Stevensville holiday rentals

We found 948 holiday rentals — enter your dates for availability
Discover a selection of 40 homes and other holiday rentals in Stevensville that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as parking and air conditioning. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Stevensville

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$2,924
for 7 nights, 1 room
AU$418 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Dining
Interior
Interior
SuperMoon rising behind the house with moon beams on the bay
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
AU$11,340
for 7 nights, 1 home
AU$1,620 per night
includes taxes & fees
Sunset Lodge on the Bay
Interior
Interior
Dining
Private kitchen
Exceptional
(107 reviews)

Cass-Away Luxury Houseboat

Grasonville

7% off
AU$1,864
for 7 nights, 1 houseboat
AU$266 per night
includes taxes & fees
Cass-Away Luxury Houseboat
Private kitchen
Terrace/patio
Room
Exterior detail
Exceptional
(5 reviews)

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Stevensville

17% off
AU$6,790
for 7 nights, 1 home
AU$970 per night
includes taxes & fees
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Interior
Private kitchen
Dining
Outdoor dining
Exceptional
(21 reviews)

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

Annapolis

16% off
AU$7,564
for 7 nights, 1 home
AU$1,081 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Sitting area overlooking Burley Creek
Enjoy screened in porch with dining table and sitting area
Lawn for yard games along the waterfront, or simply relax in the shade
Beautiful waterfront home on Burley Creek with private pier
Exceptional
(62 reviews)

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

Annapolis

8% off
AU$7,222
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
screened porch
Pool
View from Foyer into Great Room
View from Pier back to house!
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,181
for 7 nights, 1 home
AU$1,597 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Great Room
Terrace/patio
The Green Bedroom View
Kitchen - Granite Island
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,332
for 7 nights, 1 home
AU$2,047 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Swimming Pool
Porch Dining Table
Kitchen
Upstairs Hall
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
AU$18,983
for 7 nights, 1 home
AU$2,712 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Exterior
Interior
Private kitchen
Interior
Exceptional
(15 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$5,969
for 7 nights, 1 home
AU$853 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Interior
The view off of the point, breathtaking.
Pool
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,782
for 7 nights, 1 home
AU$969 per night
includes taxes & fees
Grandview- Main House
Living area
Interior
Dining
Exterior
Excellent
(6 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

8% off
AU$12,205
for 7 nights, 1 cottage
AU$1,744 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Dining
Exterior
Interior
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Exceptional
(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

8% off
AU$7,899
for 7 nights, 1 home
AU$1,128 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Convenient open-concept design: kitchen, dining and living areas
Delightful front garden welcomes you when approaching house from driveway
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,398
for 7 nights, 1 home
AU$485 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Exterior
Private kitchen
Living area
Dining
Excellent
(11 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,032
for 7 nights, 1 home
AU$719 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
outdoor space
Terrace/patio
Marina
upstairs bedroom w/ King size bed and space for queen air mattress
Exceptional
(94 reviews)

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

Pasadena

8% off
AU$5,310
for 7 nights, 1 home
AU$759 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Separate entryway with electronic keypad.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Room
Local artwork is displayed and for sale, if you wish to take a memory home.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,478
for 7 nights, 1 apartment
AU$354 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Living area
Dining
Private kitchen
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,953
for 7 nights, 1 cottage
AU$708 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Property grounds
Outdoor dining
Marina
kitchen
Exceptional
(39 reviews)

This is truly a Baydream!

Rock Hall

8% off
AU$2,932
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
This is truly a Baydream!
Dining
Exterior
Property grounds
Private kitchen
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,163
for 7 nights, 1 cottage
AU$595 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Living Room with flat screen TV and sleeper sofa
View down the lane
Dining Room - Seats 6
Sit and stay a while!
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,849
for 7 nights, 1 cottage
AU$407 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Living area
Exterior
Private kitchen
Room
Exceptional
(25 reviews)

In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Rock Hall

8% off
AU$2,474
for 7 nights, 1 home
AU$353 per night
includes taxes & fees
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Private kitchen
Living area
Interior
Exterior
Exceptional
(51 reviews)

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

Stevensville

8% off
AU$9,049
for 7 nights, 1 home
AU$1,293 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
House front
Front gardens
Interior
Property grounds
Exceptional
(63 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
AU$3,112
for 7 nights, 1 home
AU$445 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!

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Explore the waterfront setting in Stevensville

The island views and other outdoor surroundings create an inviting atmosphere in Stevensville. This relaxing and romantic city is well known for its restaurants, spas and cycling. 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 Stevensville

Are you hoping to find top things to see and do in the city? Venture out of your cosy holiday rental and check out everything that makes Stevensville a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Queenstown Harbor Golf (7.9 mi / 12.7 km)
  • St. Michaels Winery (14.7 mi / 23.6 km)
  • Maryland Renaissance Festival (14.8 mi / 23.8 km)
  • Thanksgiving Farm Wines (18.4 mi / 29.7 km)
  • Chesapeake Beach Water Park (23.2 mi / 37.4 km)
  • Paul Reed Smith Guitars (0.5 mi / 0.8 km)

Exploring the natural features in Stevensville

Whether you're an active traveller or just want to take in the scenery, Stevensville is a great spot to appreciate mother nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Northern Chesapeake Bay (2 mi / 3.2 km)
  • Sandy Point Beach (4.8 mi / 7.8 km)
  • Eastern Neck National Wildlife Refuge (6 mi / 9.7 km)
  • Maryland Quiet Waters Park (10.2 mi / 16.3 km)
  • Fort Smallwood Park (14.7 mi / 23.6 km)
  • Patuxent River (29.6 mi / 47.6 km)

Travelling to and around Stevensville

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 17.8 mi (28.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Baltimore Washington International Airport (BWI), which is 23.5 mi (37.8 km) away.

Frequently asked questions

What is the best area to stay in Stevensville when booking a holiday rental?
When considering a holiday rental in Stevensville, Maryland, the area around Kent Island is often regarded as one of the best options. This picturesque neighbourhood offers a lovely waterfront experience, making it an ideal spot for those looking to relax by the Chesapeake Bay. You can enjoy the stunning views and perhaps indulge in some outdoor activities, such as boating or fishing.One of the top attractions in Kent Island is the Chesapeake Bay Bridge, an impressive structure that not only serves as a vital connection between the Eastern and Western Shores but also offers breathtaking views, especially at sunset. In addition, the area is home to several charming parks, such as Broadneck Park, where visitors can enjoy walking trails, playgrounds, and picnic areas.The Kent Island area features a variety of holiday rental properties, ranging from cosy cottages to spacious waterfront homes, suiting different preferences and group sizes. This diversity ensures that you can find the great place to unwind after exploring the local attractions and enjoying the natural beauty that Stevensville has to offer.
Where are the best areas for renting a beach house in Stevensville?
For renting a beach house in Stevensville, the area along the Chesapeake Bay is particularly appealing, offering a range of rental options with stunning waterfront views. The vicinity near Kent Island is popular, where beach houses often come equipped with private docks, outdoor entertaining spaces, and spacious decks that provide the ideal setting for sunset gatherings. Many properties in this area also feature modern amenities such as fully equipped kitchens, ample living spaces, and sometimes even access to community pools and tennis courts.Another attractive area is along the shores of the Bay Bridge, where you can find charming cottages and larger family homes, ideal for those looking to enjoy the beach lifestyle. These rentals often include amenities such as fire pits, outdoor grills, and easy access to sandy beaches, making them suitable for family holidays or group getaways.In addition, the nearby Terrapin Nature Park offers opportunities for hiking and birdwatching, enhancing the overall experience. Rentals in this region may also provide bicycles for exploring the scenic trails.
Are there any houseboat rentals in Stevensville?
In Stevensville, there are about 12 houseboat holiday rentals available, offering a great experience on the water. These rentals are typically located along the picturesque shores of the Chesapeake Bay, allowing guests to enjoy beautiful views and easy access to local attractions. Most houseboats come equipped with essential amenities, including kitchens for preparing meals, comfortable living areas for relaxation, and outdoor decks for soaking in the sun or enjoying evening sunsets.
What is the most popular type of holiday rental accomodation in Stevensville?
In Stevensville, holiday houses are the most popular type of holiday rental, with approximately 152 available throughout the area. These spacious properties often come equipped with multiple bedrooms, fully stocked kitchens, and ample living areas, making them ideal for families or larger groups. Many also feature outdoor spaces such as decks or patios, great for enjoying the picturesque surroundings. Additionally, there are around 20 cottages which provide a charming, rustic retreat, often located near scenic spots for relaxation. For those looking for a great experience, about 12 houseboats are available, offering a distinct stay on the water with amenities that may include kitchen facilities and comfortable sleeping quarters.
Are there any family house rentals in Stevensville?
In Stevensville, Maryland, there are plenty of family-friendly house rentals available, with around 32 options to choose from. This charming area offers easy access to the beautiful Chesapeake Bay, making it a great spot for families looking to enjoy outdoor activities. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play, ensuring a comfortable and enjoyable stay.Visitors will find themselves close to attractions such as the serene Kent Island, where cycling and walking trails abound, as well as the nearby parks and beaches ideal for family outings.
Can I rent a holiday home with a pool or hot tub in Stevensville?
In Stevensville, Maryland, there are several holiday homes available for rent that feature pools or hot tubs, with around 13 options to choose from. This charming town, situated on Kent Island, offers a variety of properties that can cater to different tastes and group sizes. Many rentals come equipped with private swimming pools, hot tubs, and outdoor entertaining areas, making them superb for families or groups looking to unwind and enjoy the pleasant surroundings.Amenities often include fully equipped kitchens, spacious living areas, and sometimes even waterfront views, enhancing the overall experience of a relaxing getaway. Additionally, the proximity to the Chesapeake Bay provides opportunities for fishing, boating, and enjoying the scenic beauty of the area.
Are there pet-friendly house rentals in Stevensville?
In Stevensville, there are several pet-friendly house rentals available, with a total of 18 options for travellers seeking to bring their furry friends along. This charming area offers a variety of holiday homes equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many of these rentals also feature outdoor spaces where pets can roam freely, providing a welcoming environment for both guests and their pets.Stevensville is conveniently located near several points of interest that cater to pet owners. The nearby Sandy Point State Park is a lovely spot for walks, offering trails and scenic views of the Chesapeake Bay, superb for enjoying a day outdoors with your pet. Additionally, the area boasts pet-friendly cafes and shops, ensuring that you and your four-legged companion can enjoy the local atmosphere together.
Are there any remote work holiday rentals in Stevensville?
In Stevensville, Maryland, there are numerous options for remote work holiday rentals, with around 168 available. Many of these properties come equipped with essential work amenities such as free Wi-Fi and dedicated workspaces, including desks or desk chairs, making them ideal for those looking to balance work with leisure.The town is conveniently located near the picturesque Chesapeake Bay, providing opportunities for outdoor activities during breaks. Travellers can enjoy local attractions such as the historic Kent Island and the scenic views from the Chesapeake Bay Bridge. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Stevensville?
In Stevensville, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature decks or patios, superb for enjoying the pleasant outdoor surroundings. Onsite parking is commonly available, which is particularly convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers, ensuring guests can enjoy a warm drink at their leisure.
When is the best time to visit Stevensville for a holiday rental?
The best time to visit Stevensville for a holiday rental is during the peak season from May to July, when the town comes alive with vibrant energy and activities. This period attracts many visitors eager to enjoy the beautiful waterfront, charming shops, and local festivals, making it a great choice for those seeking a lively option.July stands out as the most popular month, offering warm temperatures (averaging around 25 to 30 degrees Celsius) that are ideal for outdoor pursuits such as kayaking, sailing, and exploring the scenic trails nearby. Families and friends flock to the area to soak up the sun and engage in various water-based adventures along the Chesapeake Bay.For those looking for great value, consider visiting in December. While the holiday crowds are less, you can still experience the town's festive spirit, with beautifully decorated streets and local events that capture the warmth of the season. This quieter time allows for comfortable exploration of the area's attractions without the hustle and bustle of peak season.
What are the top attractions in Stevensville?
In Stevensville, visitors can explore a variety of attractions that highlight the area's natural beauty and local history. The Chesapeake Bay Environmental Centre offers walking trails and educational programs focused on the region's ecosystems, making it a great spot for nature lovers. Nearby, the Kent Island Heritage Society provides insights into the local history and culture, with exhibits and events that celebrate the region's maritime past.For those interested in outdoor activities, the scenic Matapeake State Park features beautiful beaches and picnic areas, ideal for a relaxed day by the water. The area also boasts various waterfront dining options where visitors can enjoy fresh seafood with picturesque views of the bay.
Are all fees included in the Stevensville 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 Stevensville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Stevensville 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 Stevensville holiday homes?
You can find great discounts on holiday homes in Stevensville 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 Stevensville holiday home booking on Stayz?
To find Stevensville 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 Stevensville?
A long-stay holiday home in Stevensville 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 Stevensville holiday home?
Book your Stevensville 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 Stevensville?
Prices for holiday homes in Stevensville 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 Stevensville 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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