Photo by Jennifer Crim

Stevensville Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
30 Jul - 31 Jul
Tomorrow
31 Jul - 1 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Stevensville

Floating 2 bed 2 bath condo stunning views of the bay
Guests can access the marina from this dock, where several boats are moored.

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (49)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a skylight above.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (11)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$539
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
Chesapeake Houseboat Getaway on Kent Island, Maryland
Boats docked at the marina, surrounded by calm waters and a picturesque view.

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (35)
"Such a cute and unique place to stay. Very peaceful. "
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Kitchen features a stove, oven, microwave, and large island with seating.

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

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Relax in this serene outdoor seating area with a glass-top table and wicker chairs, surrounded by a wooden deck and large windows offering views of the surrounding landscape.

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

10.0 out of 10, Exceptional, (188)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Circa 1700 Chesapeake Colonial home on the National Register.
Situated on a serene lawn, this traditional building features a symmetrical facade with evenly spaced windows and a central entrance.

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (53)
"Our boys lacrosse team stayed at Camp Wright for a few days during Spring Break 2025 while we moms stayed across the street at this awesome house with so much character! It wasn't warm enough to enjoy the pool but we made great use of the outdoor fire pit. The kitchen was also perfect for our needs. May not be your cup of tea but I loved waking up to the rooster's crow. I would stay here again in a heartbeat!!! (But don't use the front stairs.) "
Circa 1700 Chesapeake Colonial home on the National Register.
Kent Island Waterfront Cottage
Enjoy cooking in this well-equipped kitchen with a sink, microwave, oven, and refrigerator.

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (299)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Waterfront Oasis of Annapolis Star
Surround yourself with nature's serenity by the tranquil pool, complete with a soothing waterfall and lush greenery.

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is NZ$828
includes taxes & fees
31 July - 1 Aug
Waterfront Oasis of Annapolis Star
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (1)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is NZ$572
includes taxes & fees
31 July - 1 Aug
Waterfront Getaway, Dock Your Boat & Play!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (42)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Boats docked at the marina, surrounded by a serene grassy area and wooded surroundings.

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (59)
"The location and unit did not disappoint! "
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Secluded Tiny Pool House -Private Pool -Self Check in
Outdoor pool

Secluded Tiny Pool House -Private Pool -Self Check in

9.6 out of 10, Exceptional, (8)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
Secluded Tiny Pool House -Private Pool -Self Check in
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is NZ$914
includes taxes & fees
31 July - 1 Aug
Edgewater/Mayo Gateaway w/ Hot Tub
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stevensville Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful. "
Anonymous traveller 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

Frequently asked questions

Can I find a holiday rental in Stevensville?

Yes, there are holiday rentals in Stevensville close to Paul Reed Smith Guitars, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stevensville has a good selection of restaurants. Make sure you have time to check out the spas and shopping during your trip.

What are some of the best holiday rentals that Stevensville has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This highly rated holiday home rental in Stevensville is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table. Another good choice for your trip to Stevensville is Relax on Kent Island in 3 Bedroom Home w/Waterview.

How many holiday rentals will I find in Stevensville?

With 38 Expedia holiday rentals, you're guaranteed to find just the right place for your Stevensville stay.

What’s there to see and do in Stevensville?

Romancoke Wharf County Park and Island Dog Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Paul Reed Smith Guitars. Matapeake State Park and Love Point State Park are other places to visit while you're in town.

What’s a holiday rental in Stevensville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stevensville. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip.