Stevensville holiday homes

We found 945 holiday rentals — enter your dates for availability
Discover a selection of 41 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:8 Jan - 15 Jan

Room
Private kitchen
Outdoor dining
Interior
Exceptional
(21 reviews)

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

Annapolis

16% off
NZ$7,988
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
screened porch
Pool
View from Pier back to house!
Dining table- seats 10!
Exceptional
(147 reviews)

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

Easton

8% off
NZ$14,575
for 7 nights, 1 home
NZ$2,082 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor dining
Interior
SuperMoon rising behind the house with moon beams on the bay
Interior
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
NZ$14,343
for 7 nights, 1 home
NZ$2,049 per night
includes taxes & fees
Sunset Lodge on the Bay
Private kitchen
Terrace/patio
Living area
Room
Exceptional
(5 reviews)

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

Stevensville

16% off
NZ$8,844
for 7 nights, 1 home
NZ$1,263 per night
includes taxes & fees
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Upper level master bedroom
Kitchen
Kitchen
Living room
Exceptional
(16 reviews)

House near Patapsco River 2700 square feet

Pasadena

8% off
NZ$11,410
for 7 nights, 1 home
NZ$1,630 per night
includes taxes & fees
House near Patapsco River 2700 square feet
outdoor space
Terrace/patio
Living room with wood fireplace and second TV with basic channels
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
NZ$6,843
for 7 nights, 1 home
NZ$978 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Please put the umbrellas down to secure them. Volleyball in deck toy box.
The owners enjoy the local wildlife. Local osprey & herons are always fishing.
We replaced pub table with a black triangular table that is a bit more nautical.
KI Beach House has many Great Rooms for Mingling or just being by yourself.
Exceptional
(75 reviews)

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

8% off
NZ$10,278
for 7 nights, 1 home
NZ$1,468 per night
includes taxes & fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
POOL TABLE, TENNIS/PICKLE BALL RACKETS, BEACH SUPPLIES, BOARD GAMES, MOVIES
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
LARGE OPEN KITCHEN
SCREENED PORCH
Exceptional
(48 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

12% off
NZ$10,818
for 7 nights, 1 home
NZ$1,545 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Interior
The view off of the point, breathtaking.
Another view from above.
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
NZ$8,563
for 7 nights, 1 home
NZ$1,223 per night
includes taxes & fees
Grandview- Main House
Property grounds
New Kitchen 2022
Exterior
Dining room
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
NZ$5,568
for 7 nights, 1 home
NZ$795 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Living area
Interior
Dining
Interior
Wonderful
(7 reviews)

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

Royal Oak

9% off
NZ$15,758
for 7 nights, 1 cottage
NZ$2,251 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Kitchen
Kitchen
Exterior
Kitchen
Exceptional
(32 reviews)

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

Stevensville

12% off
NZ$3,608
for 7 nights, 1 room
NZ$515 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Yet another nice spot to spend an evening
Favorite night spot for my extended family, when we are there
Sunroom 1/2 - Great view of pond, Bay in distance. So much wildlife to see.
Entrance from inside. Half bath on first floor is the door on the left.
Exceptional
(217 reviews)

240' Private Beachfront @Kent Island Love Point - Great for Families

Stevensville

19% off
NZ$5,865
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
240' Private Beachfront @Kent Island Love Point - Great for Families
Patio located off of the living room is perfect for sitting out and enjoying the natural settings.
Spacious master bedroom complete with private deck and master bathroom.
Dining room with seating for 8
Games room
Exceptional
(39 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
NZ$10,675
for 7 nights, 1 home
NZ$1,525 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
Kitchen - Granite Island
Terrace/patio
Exterior
Great Room
Exceptional
(16 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
NZ$17,950
for 7 nights, 1 home
NZ$2,564 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Swimming Pool
Porch Dining Table
Exterior Rear of House and Dock
Upstairs Hall
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Galesville

8% off
NZ$23,908
for 7 nights, 1 home
NZ$3,415 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Living area
Private kitchen
Living area
Interior
Exceptional
(14 reviews)

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

Annapolis

7% off
NZ$12,301
for 7 nights, 1 home
NZ$1,757 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Interior
Living area
Room
Interior
Exceptional
(16 reviews)

Waterfront 4 BR home with private pier and boat dock

Grasonville

8% off
NZ$9,825
for 7 nights, 1 home
NZ$1,404 per night
includes taxes & fees
Waterfront 4 BR home with private pier and boat dock
Interior
Exterior
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Interior
Exceptional
(5 reviews)

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

Rock Hall

8% off
NZ$10,181
for 7 nights, 1 home
NZ$1,454 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Inquire on both homes: togetherness without everyone being under the same roof!
In Stevensville MD 5 miles to Chesapeake Bay Bridge. 20 miles o Annapolis.
Attention all "Foodies" Check out the galley! Open water views.
Big Internet TV above the table and another above dining room buffet downstairs.
Exceptional
(43 reviews)

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

8% off
NZ$10,278
for 7 nights, 1 home
NZ$1,468 per night
includes taxes & fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Room
Property grounds
Private kitchen
Beach
Exceptional
(94 reviews)

Chesapeake Bay Cottage

Churchton

8% off
NZ$4,375
for 7 nights, 1 cottage
NZ$625 per night
includes taxes & fees
Chesapeake Bay Cottage
Living area
Living area
Living area
Dining
Exceptional
(11 reviews)

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

Riva

8% off
NZ$7,364
for 7 nights, 1 home
NZ$1,052 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Dining
Private kitchen
Property grounds
Interior
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
NZ$8,048
for 7 nights, 1 home
NZ$1,150 per night
includes taxes & fees
Arcadia Shores on the Cove.
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Rear Porch for relaxing or for barbecues!
Thomas Harrison House looking from St. Michaels Town Harbor
Exceptional
(147 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
NZ$10,489
for 7 nights, 1 home
NZ$1,498 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

  • 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 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)
  • Bay Hills Golf Club (9.9 mi / 15.9 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)

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)
  • Bay Ridge Beach (8 mi / 12.9 km)
  • Maryland Quiet Waters Park (10.2 mi / 16.3 km)
  • Fort Smallwood Park (14.7 mi / 23.6 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Stevensville holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Stevensville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.