Annapolis holiday rentals

We found 717 holiday rentals — enter your dates for availability
Select from 384 houses, 45 apartments and other holiday rentals to find the perfect place for your stay in Annapolis. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Annapolis

Showing deals for:18 Dec - 25 Dec

Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(31 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
AU$2,946
for 7 nights, 1 room
AU$421 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Outdoor dining
Private kitchen
Room
Interior
Exceptional
(21 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$7,767
for 7 nights, 1 home
AU$1,110 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Upstairs Hall
Porch Dining Table
Exterior Rear of House and Dock
Kitchen
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
AU$18,963
for 7 nights, 1 home
AU$2,709 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Great Room
Terrace/patio
Exterior
The Green Bedroom View
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,317
for 7 nights, 1 home
AU$2,045 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
Sitting area overlooking Burley Creek
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(62 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off
AU$7,214
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Private kitchen
Interior
Exterior
Exterior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$5,962
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Living area
Private kitchen
Interior
Living area
Exceptional
(14 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

7% off
AU$12,164
for 7 nights, 1 home
AU$1,738 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Living area
Private kitchen
Dining
Exterior
Excellent
(11 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,060
for 7 nights, 1 home
AU$723 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
upstairs bedroom w/ King size bed and space for queen air mattress
Terrace/patio
Marina
Living room with wood fireplace and second TV with basic channels
Exceptional
(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
AU$5,304
for 7 nights, 1 home
AU$758 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Property grounds
New Kitchen 2022
Interior
Exterior
Exceptional
(65 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,137
for 7 nights, 1 home
AU$734 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior
Living area
Interior
Private kitchen
Exceptional
(51 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$9,040
for 7 nights, 1 home
AU$1,291 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Exterior
Terrace/patio
Living area
Dining
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,200
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Separate entryway with electronic keypad.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Local artwork is displayed and for sale, if you wish to take a memory home.
Room
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,475
for 7 nights, 1 apartment
AU$354 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Screen porch for relaxing, eating, watching the water, working on a laptop
Pool
Exterior
Dining
Exceptional
(58 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

16% off
AU$4,748
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Dining
Living area
Living area
Living area
Exceptional
(11 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
AU$5,777
for 7 nights, 1 home
AU$825 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Private kitchen
Dining
Exterior
Living area
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$6,783
for 7 nights, 1 home
AU$969 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Exterior
Pool
Interior
Marina
Exceptional
(233 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,595
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Sun Room
2nd Floor Full Bath
Rear of House
Living Room
Exceptional
(180 reviews)

Heart of Historic District!

Annapolis

26% off
AU$4,542
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Heart of Historic District!
Living area
Exterior
Property grounds
Room
Exceptional
(269 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
AU$1,671
for 7 nights, 1 cottage
AU$239 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Property grounds
Pool
Private kitchen
Interior
Exceptional
(217 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off
AU$4,569
for 7 nights, 1 room
AU$653 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Private kitchen
Exterior
Property grounds
Living area
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

8% off
AU$4,336
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Ship's Ladder Stairs to Rooftop Deck
Historic Annapolis and City Dock
Quaint Pinkney Street
Living Room with Cable Television
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,170
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Room
Private kitchen
Dining
Living area
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

7% off
AU$7,894
for 7 nights, 1 home
AU$1,128 per night
includes taxes & fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Interior
Interior
Exterior
Marina
Exceptional
(55 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
AU$1,792
for 7 nights, 1 cottage
AU$256 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Annapolis

  • Historic District: Stroll through Annapolis' charming streets filled with well-preserved colonial architecture and historic landmarks.
  • Vibrant Waterfront: Enjoy the scenic Annapolis harbour, perfect for leisurely walks, boat tours, and stunning views.
  • Maritime Heritage: Immerse yourself in the city’s rich maritime history, with museums and maritime activities reflecting its nautical past.
  • Cultural Experiences: Discover local art galleries and theatres showcasing the vibrant arts scene unique to Annapolis.
  • Outdoor Adventures: Explore urban parks and outdoor spaces, ideal for families and nature lovers seeking recreation.

Popular types of accommodation in Annapolis

Planning a getaway to Annapolis, Maryland? This charming city, known for its rich maritime history and vibrant arts scene, offers a delightful array of holiday rental options, including private homes, cosy cottages, and stylish apartments. While you explore the historic district, the stunning waterfront, and iconic landmarks, enjoy the comfort and convenience of your chosen accommodation. Discover the perfect rental to enhance your Annapolis experience.

  • Private Holiday Homes: Discover the charm of secluded retreats offering complete privacy and a homely feel in Annapolis.
  • Cottages: Enjoy cosy, quaint dwellings with a touch of rustic appeal, ideal for a peaceful escape.
  • Apartments: Opt for modern, well-equipped urban flats, perfect for experiencing city life in comfort.
  • Condos: Experience stylish, contemporary living with shared amenities in a vibrant setting.
  • Villas: Indulge in spacious, elegant residences that provide a luxurious and relaxing stay.**

Top attractions in Annapolis

Annapolis, Maryland offers a charming blend of urban parks, marinas, and historic houses, making it an ideal destination for families and outdoor enthusiasts. Explore the vibrant Annapolis harbour and immerse yourself in the city's rich culture and history. Whether you're enjoying leisurely walks or seeking cultural experiences, Annapolis promises memorable adventures in a picturesque setting.

  • Chesapeake Bay Bridge: A modern bridge with city vibes, offering magnificent views and a seamless connection through Annapolis. Its sleek design stands out in the urban landscape.
  • Sandy Point State Park: A national state park providing outdoor, scenic adventures and a breath of fresh air with its picturesque settings and ample space for exploration.
  • Maryland State House: A historic civic government building exuding culture vibes, inviting visitors to appreciate its storied past and architectural splendour.

Things to do recommended for couples

Explore Annapolis with your loved one while strolling through historic streets, enjoying a boat ride on the water, and indulging in delightful harbour views, all offering a romantic escape in this charming town.

Things to do recommended for families

Families will delight in exploring the United States Naval Academy, where they can enjoy fascinating exhibits and tours. The nearby Chesapeake Bay offers opportunities for sailing and kayaking, while the historic downtown area boasts charming shops and eateries perfect for a leisurely family day out.

Things to do recommended for groups

Discover the maritime legacy and vibrant culture of Annapolis. Enjoy scenic harbour walks, savour local seafood delicacies and engage in interactive group activities that bring history and community to life.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Annapolis

Whether you are travelling with a group, as a family, with your pets, or seeking extended stays, be sure to filter by the appropriate priorities. Here are some Stayz booking tips for you.

  • Traveling to Annapolis with a group: Consider how many bedrooms you require, along with facilities like a fully equipped kitchen or an outdoor area suitable for group gatherings. Fortunately, you can refine your search on Stayz to include all these features and more.
  • Traveling to Annapolis with young kids: Traveling with young children can present its challenges. It is important to prioritise their comfort and safety, while also ensuring age-suitable facilities, such as a private swimming pool, are available. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Annapolis: For many, a family holiday isn’t truly complete without their beloved pet by their side. If you can relate to this, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Annapolis: If you're seeking holiday lets with special offers for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly discover and secure savings on monthly rentals. You might also want to consider refining your search to include a parking space, a well-equipped kitchen, or a private pool.

Where to stay in and around Annapolis

Discover Annapolis, a charming state capital with a blend of historical allure and modern vibrancy. Wander through picturesque streets, explore family-friendly neighbourhoods, and enjoy outdoor excursions in the heart of the city. Experience the best of Annapolis with a mix of cultural gems and relaxing spots that capture the essence of this delightful urban retreat.

  • Historic District: Nestled in the heart of Annapolis, the Historic District is a vibrant neighbourhood that encapsulates a rich tapestry of history and modern urban delights. Visitors can immerse themselves in a family-friendly, outdoorsy, city-themed experience, exploring educational landmarks such as an academy and a bustling tourist precinct. The area also offers a delightful shopping scene with both a shopping area and centre, alongside a picturesque dock port that whispers tales of maritime heritage.
  • Arnold: Located a short 6km journey from Annapolis, Arnold is a charming city that invites travellers to savour scenic outdoor adventures and family-oriented activities. With an emphasis on education and leisure, the city boasts a well-regarded golf course and offers delightful experiences by the bay, a sandy beach, and a serene lake, making it a perfect spot for those who appreciate a blend of nature and recreation.
  • Arundel on the Bay: Arundel on the Bay is a captivating neighbourhood that promises a refreshing mix of outdoor, beach, and scenic experiences. Situated conveniently within the Annapolis area, it is known for its inviting recreational areas and a bustling shopping centre. Visitors can enjoy the serene beauty of the nearby beach and bay while also exploring local educational landmarks like the academy, ensuring a culturally enriching and leisurely holiday for all.

Best time to go to Annapolis

If you're planning a trip to Annapolis, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnyModerately LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyModerately LowSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyModerately HighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

Booking with Stayz is a breeze

Looking to cut costs on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. You might also secure substantial savings by planning a longer stay. To locate a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday let.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers a handy space to create new trips, resume where you previously left off, or review and arrange your plans. Your saved or booked properties are neatly organised into categories labeled Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Annapolis

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Thanksgiving Farm Wines (10.4 mi / 16.8 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Queenstown Harbor Golf (17.4 mi / 28 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)
  • Chesapeake Beach Water Park (19.9 mi / 32.1 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Northern Chesapeake Bay (8 mi / 12.8 km)
  • Fort Smallwood Park (11 mi / 17.6 km)
  • Allen Pond Park (13.4 mi / 21.5 km)
  • Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 16.8 mi (27 km) away.

Frequently asked questions

What is the best area to stay in Annapolis when booking a holiday rental?
When considering a holiday rental in Annapolis, Maryland, the historic downtown area is one of the best choices. This charming neighbourhood is steeped in history and offers a vibrant setting, making it a favourite among visitors. Here, you'll find a delightful array of properties, from quaint cottages to elegant townhouses. The proximity to the waterfront is a major draw, allowing easy access to scenic views and leisurely strolls along the docks.One of the top attractions in downtown Annapolis is the Maryland State House, the oldest state capitol still in continuous use, which showcases stunning architecture and rich American history. Another highlight is the United States Naval Academy, where you can explore its beautiful grounds and learn about its storied tradition. The area's cobblestone streets are lined with charming boutiques, restaurants, and galleries, providing plenty of options for dining and shopping.If you prefer a more residential feel, Eastport is another excellent choice. This neighbourhood, just across the water from downtown, offers a mix of waterfront properties and cosy homes, along with a relaxed vibe. Eastport is known for its local eateries and boutique shops, and it's just a short walk or boat ride from the bustling downtown area.
Where are the best areas for renting a beach house in Annapolis?
For renting a beach house in Annapolis, the area around the Chesapeake Bay is highly desirable. The Eastport neighbourhood, located just across the water from downtown Annapolis, is particularly popular for its charming waterfront properties. Many rentals here offer stunning views of the bay, private docks, and easy access to local marinas, making them superb for those interested in boating or fishing. Guests can expect amenities such as spacious decks for outdoor dining, modern kitchens, and comfortable living areas, ideal for family gatherings or relaxing after a day on the water.Another great option is the Cape St. Claire community, which features a mix of traditional beach cottages and more modern homes. This area provides a laid-back atmosphere with access to sandy beaches and picnic areas, along with amenities like outdoor showers, fire pits, and community facilities. Visitors can enjoy local parks and trails, superb for walking or cycling, and the proximity to local shops and restaurants adds to the convenience.For those looking for a more secluded experience, the properties along Broadneck Park offer a tranquil setting with easy access to the bay. Rentals in this area often include features like large yards, private balconies, and family-friendly amenities, making them an excellent choice for travellers seeking a peaceful retreat while still being close to the attractions of Annapolis.
Are there any houseboat rentals in Annapolis?
In Annapolis, there are about 16 houseboat holiday rentals available, primarily located along the scenic waterfront and in marinas close to the historic district. These unique accommodations offer a blend of nautical charm and modern comfort, with most featuring amenities such as fully equipped kitchens, spacious living areas, and outdoor decks superb for enjoying the views of the Chesapeake Bay. Many houseboats are conveniently situated near popular attractions like the United States Naval Academy and the vibrant City Dock, allowing guests to immerse themselves in the local culture and dining options.
What is the most popular type of holiday rental accomodation in Annapolis?
In Annapolis, holiday houses are the most popular type of holiday rental, with around 1,204 available throughout the city. These properties are often located in charming neighbourhoods close to the historic district, providing easy access to attractions such as the United States Naval Academy and the waterfront. Most holiday houses come equipped with multiple bedrooms, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a home-like experience.Apartments are also a top option, with approximately 180 available, typically featuring modern amenities and convenient locations near local shops and restaurants. For those seeking a great experience, there are about 88 cottages and 88 condos, which often provide picturesque views and outdoor spaces for relaxation. Additionally, a few houseboats are available for a distinctive stay on the water.
Are there any family house rentals in Annapolis?
In Annapolis, Maryland, there are numerous family-friendly house rentals available, with around 257 options throughout the city. This charming area is known for its maritime heritage, historic architecture, and vibrant waterfront, making it an excellent choice for families. Many properties in neighbourhoods such as Eastport and the Historic District offer spacious living areas, fully equipped kitchens, and outdoor spaces that are superb for children to enjoy.Visitors can find amenities like Wi-Fi, air conditioning, and sometimes even features such as game rooms or backyards with grills, enhancing the family experience. Moreover, being close to attractions like the U.S. Naval Academy, the Maryland State House, and the picturesque City Dock allows families to easily engage in educational and recreational activities together.
Can I rent a holiday home with a pool or hot tub in Annapolis?
In Annapolis, there are several holiday homes available for rent that feature pools and hot tubs, with around 38 options to choose from. This charming city, known for its maritime heritage and historic architecture, offers a variety of neighbourhoods where these properties can be found, including the picturesque Eastport area, which is close to the waterfront and offers stunning views, and the quaint Historic District, where visitors can explore cobblestone streets and local shops.Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for entertaining. Many properties also come with fully equipped kitchens, allowing for convenient meal preparation, and some may feature additional luxuries such as outdoor dining spaces, fire pits, and easy access to local attractions.
Are there pet-friendly house rentals in Annapolis?
In Annapolis, there are numerous pet-friendly house rentals available, with around 149 options to choose from. The city offers a charming blend of historic architecture and waterfront views, making it a delightful destination for pet owners. Many holiday rentals come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, allowing for a relaxing stay with your furry companions.The neighbourhood around the historic district is particularly appealing, with properties that provide easy access to local parks and the scenic waterfront. The nearby Quiet Waters Park features lovely walking trails and open spaces, superb for exercising pets, while the Broadneck Park offers additional recreational areas for outdoor activities. Additionally, the city's dog-friendly cafes and shops enhance the experience for travellers with pets, ensuring both comfort and convenience during their stay. See all pet-friendly rentals in Annapolis.
Are there any remote work holiday rentals in Annapolis?
In Annapolis, there are a significant number of remote work holiday rentals available, with around 1,492 options to choose from. This charming city, known for its rich maritime history and vibrant culture, provides an excellent backdrop for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated workspaces or desks, and comfortable living areas that allow for a productive environment.Travellers can expect a variety of accommodations, ranging from quaint cottages to spacious homes, often featuring modern kitchens and outdoor spaces great for a break from work. The historic downtown area, with its picturesque streets and waterfront views, offers plenty of opportunities for relaxation after a day of remote working. Additionally, the proximity to local attractions such as the United States Naval Academy and the scenic Annapolis Harbor adds to the appeal. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Annapolis?
In Annapolis, popular rental amenities include well-equipped kitchens, which allow guests to prepare meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant Maryland weather. A coffee and tea maker is commonly found in rentals, ensuring visitors can enjoy their morning brew at their convenience. Onsite parking is another sought-after amenity, making it easier for guests to explore the historic downtown area and the scenic waterfront.
When is the best time to visit Annapolis for a holiday rental?
The best time to visit Annapolis for a holiday rental is during the peak season from May to July. This vibrant period is particularly popular among travellers looking to enjoy the city's rich maritime culture and beautiful waterfront. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as sailing, kayaking, and exploring the historic streets lined with charming shops and eateries.July stands out as the most popular month, attracting families and groups eager to experience the lively option created by festivals and events, including the renowned Annapolis Arts & Wine Festival. Visitors can take advantage of longer daylight hours to soak in the sights, making it a truly delightful experience.For those looking to maximise their budget while still enjoying the beauty of Annapolis, consider a trip in November. This month, while quieter, offers a unique charm with fewer crowds, allowing for leisurely strolls through the picturesque downtown and the chance to enjoy local dining without the rush of peak season.
What are the top attractions in Annapolis?
In Annapolis, visitors can take part in a rich maritime heritage and vibrant culture. The historic district is a must-see, featuring charming historic architecture and attractions like the Maryland State House, where the Continental Congress once met. Here, holiday rentals often reflect the area's history and provide easy access to local shops and restaurants.The United States Naval Academy is another key attraction, offering guided tours that showcase its impressive grounds and museums. Nearby, the scenic waterfront along City Dock is superb for leisurely strolls and dining, with stunning views of the boats and the Chesapeake Bay.For those who appreciate nature, Sandy Point State Park provides a beautiful setting for picnics, hiking, and beach activities, all just a short drive from the city centre.
Are all fees included in the Annapolis holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Annapolis holiday homes with parking?
Stayz offers a wide selection of holiday homes in Annapolis with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Annapolis holiday homes?
You can find great discounts on holiday homes in Annapolis on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Annapolis holiday home booking on Stayz?
To find Annapolis holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Annapolis?
A long-stay holiday home in Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Annapolis holiday home?
Book your Annapolis holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Annapolis?
Prices for holiday homes in Annapolis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Annapolis to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas