Chesapeake Beach holiday rentals

We found 836 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Chesapeake Beach that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, which might include parking and a fireplace. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Chesapeake Beach

Showing deals for:20 Nov - 27 Nov

Upstairs Hall
Porch Dining Table
Swimming Pool
Exterior Rear of House and Dock
Exceptional
(34 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
AU$18,804
for 7 nights, 1 home
AU$2,686 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Great Room
Terrace/patio
Kitchen - Granite Island
Exterior
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,201
for 7 nights, 1 home
AU$2,029 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Marina
Property grounds
Exterior
Room
Exceptional
(9 reviews)

Houseboat on Solomons Island

Solomons

8% off
AU$3,145
for 7 nights, 1 houseboat
AU$449 per night
includes taxes & fees
Houseboat on Solomons Island
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
West-facing screened porch with bar area and café lights for night ambience
Sitting area overlooking Burley Creek
Exceptional
(62 reviews)

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

Annapolis

8% off
AU$7,514
for 7 nights, 1 home
AU$1,073 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Living area
Property grounds
Beach
Private kitchen
Exceptional
(92 reviews)

Chesapeake Bay Cottage

Churchton

8% off
AU$3,444
for 7 nights, 1 cottage
AU$492 per night
includes taxes & fees
Chesapeake Bay Cottage
Exterior
Interior
Private kitchen
Interior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$5,914
for 7 nights, 1 home
AU$845 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Living area
Dining
Exterior
Terrace/patio
Exceptional
(5 reviews)

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Lusby

8% off
AU$5,760
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Exterior
Terrace/patio
Dining
Private kitchen
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,173
for 7 nights, 1 home
AU$453 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Room
Private kitchen
Living area
Interior
Exceptional
(12 reviews)

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

Annapolis

8% off
AU$13,354
for 7 nights, 1 home
AU$1,908 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Exterior
Private kitchen
Dining
Dining
Excellent
(9 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,019
for 7 nights, 1 home
AU$717 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Living area
Outdoor dining
Living area
Interior
Exceptional
(5 reviews)

Driftwood Haven, Chesapeake Bay views throughout

Lusby

12% off
AU$4,715
for 7 nights, 1 home
AU$674 per night
includes taxes & fees
Driftwood Haven, Chesapeake Bay views throughout
Local artwork is displayed and for sale, if you wish to take a memory home.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Room
Separate entryway with electronic keypad.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

8% off
AU$2,457
for 7 nights, 1 apartment
AU$351 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Dining
Exterior
Property grounds
Living area
Wonderful
(17 reviews)

Magnificent Water Front Property

Solomons

7% off
AU$7,966
for 7 nights, 1 home
AU$1,138 per night
includes taxes & fees
Magnificent Water Front Property
dining area
entryway
steps to the loft
loft bedroom
Exceptional
(58 reviews)

Soul Oasis - home on the Chesapeake Bay

Lusby

8% off
AU$1,871
for 7 nights, 1 cottage
AU$267 per night
includes taxes & fees
Soul Oasis - home on the Chesapeake Bay
Interior
Living area
Living area
Living area
Exceptional
(11 reviews)

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

Riva

8% off
AU$5,730
for 7 nights, 1 home
AU$819 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Beautiful North Bach, MD
Beautiful North Beach, MD
Directly next door to Sunrise Garden park
Open-concept living area and kitchen
Exceptional
(21 reviews)

Unbelievable beach views for 6

North Beach

8% off
AU$3,445
for 7 nights, 1 apartment
AU$492 per night
includes taxes & fees
Unbelievable beach views for 6
Room
Foyer
Bathroom
Exterior
Exceptional
(27 reviews)

Guest Quarters at the Inn - 102

North Beach

8% off
AU$2,069
for 7 nights, 1 apartment
AU$296 per night
includes taxes & fees
Guest Quarters at the Inn - 102
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Light and bright dining room with space for 6 (plus a high chair).
Exceptional
(8 reviews)

Cozy Cottage with Beach Access

Annapolis

8% off
AU$4,578
for 7 nights, 1 home
AU$654 per night
includes taxes & fees
Cozy Cottage with Beach Access
Gourmet Kitchen with seating at the counter for 5
Open floor plan
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Exterior
Exceptional
(58 reviews)

Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience

Annapolis

6% off
AU$7,032
for 7 nights, 1 home
AU$1,005 per night
includes taxes & fees
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Property grounds
Outdoor dining
Exterior detail
Living area
Exceptional
(11 reviews)

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

Huntingtown

8% off
AU$5,061
for 7 nights, 1 cottage
AU$723 per night
includes taxes & fees
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Living area
Exterior
Outdoor dining
Property grounds
Exceptional
(267 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
AU$1,659
for 7 nights, 1 cottage
AU$237 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Exterior
Outdoor dining
Exterior detail
Outdoor dining
Exceptional
(172 reviews)

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

St. Leonard

6% off
AU$2,098
for 7 nights, 1 cottage
AU$300 per night
includes taxes & fees
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
Wiew out east side windows
Hilltop cottage December
Partial view of the water
Private kitchen
Exceptional
(29 reviews)

Quiet Woodland cottage near St. Leonard's Creek

Lusby

8% off
AU$1,145
for 7 nights, 1 cottage
AU$164 per night
includes taxes & fees
Quiet Woodland cottage near St. Leonard's Creek
Fully equipped and filled with light, the kitchen opens to the backyard for easy outdoor dining.
The upstairs primary suite includes a queen bed and private bath with a deep soaking tub—your own peaceful hideaway.
Dining
Park with ease in the permeable gravel driveway and enjoy sustainable living with rooftop solar panels and lush native landscaping.
Exceptional
(6 reviews)

Unique and central in Eastport

Annapolis

8% off
AU$5,768
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
Unique and central in Eastport

  • 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

Explore the beachside setting in Chesapeake Beach

Enjoy the live music and other features of Chesapeake Beach. This relaxing and romantic city is well known for its restaurants, spas and beaches. 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 Chesapeake Beach

Are you hoping to find attractions to see during your stay? Venture out of your holiday home and experience everything that makes Chesapeake Beach a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Beach Water Park (0.2 mi / 0.3 km)
  • Thanksgiving Farm Wines (13.1 mi / 21.1 km)
  • Running Hare Vineyard (13.6 mi / 21.9 km)
  • Lake Presidential Golf Club (14.9 mi / 24 km)
  • Renditions Golf Club (16.5 mi / 26.6 km)
  • South River Golf Links (15.7 mi / 25.2 km)

Exploring the natural features in Chesapeake Beach

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chesapeake Beach is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (5.2 mi / 8.3 km)
  • Triton Beach (13.3 mi / 21.3 km)
  • Matoaka Beach (15.7 mi / 25.3 km)
  • Flag Ponds Nature Park (17.3 mi / 27.8 km)
  • Northern Chesapeake Bay (21.3 mi / 34.3 km)
  • Blackwater National Wildlife Refuge (29.2 mi / 47 km)

Seasonal weather averages in Chesapeake Beach

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 24°C.

How to get to and around Chesapeake Beach

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.5 mi (42.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the best area to stay in Chesapeake Beach when booking a holiday rental?
When considering a holiday rental in Chesapeake Beach, Maryland, the area around the waterfront is particularly appealing. This neighbourhood offers a charming coastal atmosphere, with stunning views of the Chesapeake Bay and easy access to the beach. Visitors will find a variety of properties available, ranging from quaint cottages to more spacious homes, providing a range of options for different group sizes.One of the top attractions in this area is the Chesapeake Beach Railway Museum, which offers a glimpse into the local history and the significance of the railway in the area's development. Additionally, the nearby Calvert Cliffs State Park is superb for those who enjoy outdoor activities, featuring hiking trails and opportunities for fossil hunting along the stunning cliffs.
Where are the best areas for renting a beach house in Chesapeake Beach?
For renting a beach house in Chesapeake Beach, the area along the Chesapeake Bay offers a delightful selection of properties. The shoreline near the Calvert Cliffs State Park is particularly appealing, as it provides easy access to sandy beaches and picturesque views of the bay. Many of the beach houses in this vicinity boast amenities such as spacious decks, modern kitchens, and outdoor grilling areas, making them superb for families or groups looking to enjoy a seaside getaway.In addition, the area around the Chesapeake Beach Resort and Spa features holiday rentals that often include access to community pools, hot tubs, and private beach access. These properties are well-equipped for relaxation and entertainment, with some offering game rooms or fire pits for evening gatherings.Moreover, the nearby boardwalk and local shops add to the charm, giving visitors the opportunity to explore dining options and leisure activities. Rentals in this part of Chesapeake Beach frequently come with essentials like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay.
What is the most popular type of holiday rental accomodation in Chesapeake Beach?
In Chesapeake Beach, holiday houses and cottages are the most popular types of holiday rentals, with around 16 of each available in the area. These properties often provide a cozy feel, featuring multiple bedrooms, spacious living areas, and fully equipped kitchens, great for families or groups looking to enjoy a relaxing getaway. Many of these rentals also include outdoor spaces such as decks or gardens, allowing guests to take advantage of the pleasant Maryland weather. Additionally, there are several apartments available, offering a more compact option for those seeking a convenient base near the beach and local attractions.
Are there any family house rentals in Chesapeake Beach?
In Chesapeake Beach, there are several family-friendly house rentals available, making it an ideal spot for a family getaway. This charming coastal town features properties that often boast spacious living areas and fully equipped kitchens, great for preparing meals together after a day of exploring. Many homes also include outdoor spaces where children can play and families can gather for barbecues.Visitors can enjoy the close proximity to the beach, where activities such as swimming, fishing, and sunbathing await. The local area is also home to attractions like the Chesapeake Beach Railway Museum, which offers a glimpse into the town's history, and nearby parks that provide ample opportunities for outdoor recreation.
Can I rent a holiday home with a pool or hot tub in Chesapeake Beach?
In Chesapeake Beach, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful choice for those seeking relaxation and leisure. This coastal town offers a variety of properties, many of which are located near the waterfront, providing scenic views and easy access to the beach.Travellers can expect a range of amenities in these rentals, such as private pools, hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens suitable for family meals. Some properties may also include features like barbecue grills and comfortable lounge areas, great for enjoying the pleasant Maryland weather.
Are there pet-friendly house rentals in Chesapeake Beach?
In Chesapeake Beach, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties are situated close to the waterfront, offering stunning views of the Chesapeake Bay. Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios, great for enjoying the coastal breeze.The area is known for its charming beach atmosphere, with access to local attractions such as the Chesapeake Beach Water Park, ideal for family outings, and nearby parks where pets can enjoy some exercise. Additionally, the local community often features pet-friendly dining options, making it easy to explore the area without leaving your pet behind.
Are there any remote work holiday rentals in Chesapeake Beach?
In Chesapeake Beach, there are numerous holiday rentals suitable for remote work, with around 28 options available. This charming coastal town offers a variety of properties that cater to the needs of those working remotely. Many of these rentals provide essential amenities such as high-speed Wi-Fi, dedicated workspaces or desks, and comfortable living areas, ensuring a productive environment while enjoying the scenic surroundings.The area is known for its beautiful waterfront views and access to local attractions, including the Chesapeake Beach Railway Museum and the nearby Calvert Cliffs State Park, which offers excellent hiking opportunities. visitors can expect properties that often feature well-equipped kitchens, outdoor spaces for relaxation, and easy access to the beach, making it a great blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chesapeake Beach?
In Chesapeake Beach, popular rental amenities often include kitchens, allowing guests to prepare their own meals while enjoying the convenience of home. Many properties feature decks or patios, great for relaxing outdoors and soaking up the scenic views of the coastline. Balconies are also common, providing a private spot to enjoy morning coffee or evening sunsets. Additionally, air conditioning ensures comfort during warmer months, while fireplaces add a cosy touch for cooler evenings.
When is the best time to visit Chesapeake Beach for a holiday rental?
The best time to visit Chesapeake Beach for a holiday rental is during the summer months, particularly in July, when the town is bustling with activity. This peak season, spanning from June to August, invites families and beach enthusiasts to enjoy the warm coastal climate, with temperatures typically ranging from 24 to 32 degrees Celsius. Visitors can indulge in a variety of outdoor activities, from swimming in the Atlantic to exploring local parks and enjoying fresh seafood at waterfront restaurants.In July, the atmosphere is vibrant, with many opportunities for live music, festivals, and community events that enhance the holiday experience. The beach is alive with energy, making it an ideal time for those who love socialising and engaging in lively outdoor pursuits.For those looking for budget-friendly options, consider planning your trip in December. While this month falls within the low tourist season, it presents a unique chance to enjoy Chesapeake Beach's peaceful winter charm. You can explore the area's natural beauty without the crowds and take part in the local holiday festivities.Ultimately, your choice of when to visit Chesapeake Beach will depend on your preference for lively summer days filled with beach fun or the tranquil beauty of the off-peak winter season.
What are the top attractions in Chesapeake Beach?
In Chesapeake Beach, visitors can enjoy a range of attractions that highlight the area's coastal charm. The Chesapeake Beach Railway Museum offers insights into the town's history, showcasing its past as a popular seaside resort. Along the waterfront, the beach itself is a key attraction, superb for sunbathing, swimming, and enjoying picturesque sunsets over the Chesapeake Bay.For outdoor enthusiasts, the nearby North Beach boardwalk provides a pleasant walking path with beautiful views, as well as access to local shops and eateries. The area's proximity to water activities means that visitors can partake in fishing, boating, and crabbing, making it an ideal spot for those who enjoy the outdoors.Additionally, families will value the fun at the Chesapeake Beach Water Park, which features various slides and pools, ensuring a day of excitement for children and adults alike.
Are all fees included in the Chesapeake Beach 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 Chesapeake Beach holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesapeake Beach 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 Chesapeake Beach holiday homes?
You can find great discounts on holiday homes in Chesapeake Beach 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 Chesapeake Beach holiday home booking on Stayz?
To find Chesapeake Beach 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 Chesapeake Beach?
A long-stay holiday home in Chesapeake Beach 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 Chesapeake Beach holiday home?
Book your Chesapeake Beach 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 Chesapeake Beach?
Prices for holiday homes in Chesapeake Beach 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 Chesapeake Beach 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.

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