A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

Stevensville Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Stevensville vacation rentals

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

1. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

$284 nightly

Nov 9 - Nov 10

Total with taxes and fees

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

Anthony P.

$324 nightly

Nov 23 - Nov 24

Total with taxes and fees

Three birds perched on a wooden structure by the water.

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

Stevensville

barbara s.

$1,141 nightly

Dec 1 - Dec 2

Total with taxes and fees

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

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

Stevensville

David R.

$1,141 nightly

Dec 1 - Dec 2

Total with taxes and fees

A two-story house with a red roof, a brick chimney, and a small porch.

5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

Anonymous traveler

$945 nightly

Nov 8 - Nov 9

Total with taxes and fees

A deck with a view of a marina, including boats and docks.

6. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$233 nightly

Nov 12 - Nov 13

Total with taxes and fees

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

7. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

$293 nightly

Nov 6 - Nov 7

Total with taxes and fees

A house with a blue front door, two windows, and a small porch.

8. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

$251 nightly

Nov 6 - Nov 7

Total with taxes and fees

Stylish kitchen with open layout and island seating

9. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$423 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

10. Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

Guillaume P.

$175 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

11. Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Linda B.

$276 nightly

Nov 9 - Nov 10

Total with taxes and fees

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

12. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hot tub with a white deck and railing, surrounded by trees and a house in the background.

13. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

$404 nightly

Nov 9 - Nov 10

Total with taxes and fees

Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

14. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold

Anonymous traveler

$352 nightly

Nov 15 - Nov 16

Total with taxes and fees

A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

15. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena

Charles W.

$383 nightly

Nov 8 - Nov 9

Total with taxes and fees

A building with a gabled roof and a circular vent on the roof.

16. BAYSIDE BUNGALOW

Rock Hall

Diane V.

$272 nightly

Nov 6 - Nov 7

Total with taxes and fees

A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

17. Lower Level Loft - Adorable Studio Apt. Near BWI

South Gate

Deanna

$74 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Jennifer H.

$483 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

19. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

$489 nightly

Nov 30 - Dec 1

Total with taxes and fees

A kitchen with wooden cabinets, granite countertops, and a dining table set with blue and white dishes.

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

"A nice, clean, roomy place at a good price--gotta love that. The walk-out basement apartment was located in a compound of units on a quiet dead-end street. This unit is actually toward the back and I spent a little time searching for it. Once there, access to the key and apartment was no problem.The home was well-stocked with kitchen and bathroom supplies, and bedding. Would definitely stay there again."

Rob L.

$440 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Stevensville Hotel Reviews

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A balcony with a view of a body of water, a row of buildings, and a chair.

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

Best Western Kent Narrows Inn

Grasonville

10/10 Excellent

Valerie

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

Quality Inn Grasonville near Kent Island

Grasonville

10/10 Excellent

My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any...

Chuck

A white two-story building with a central entrance, a staircase, and a small garden area.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Robert

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Celina

A two-story house with a covered porch, a staircase, and a garden area.

Haven Point Inn and Gallery

Rock Hall

10/10 Excellent

Joe

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

A hotel with a covered entrance, large columns, and a brick facade.

Holiday Inn Express & Suites Annapolis by IHG

Annapolis

10/10 Excellent

Marc

Find out more about Stevensville

Everything you need to know about Stevensville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stevensville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stevensville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stevensville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stevensville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stevensville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stevensville rentals

At Expedia, we put the best Stevensville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stevensville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stevensville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stevensville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Stevensville?

Yes, we have vacation rentals in Stevensville near Paul Reed Smith Guitars, or you can choose a more secluded option if you'd like a relaxing place to stay. Our travelers say Stevensville has a good selection of restaurants. Make sure you have time to check out the spas and shopping during your trip.

What's the top vacation rental in Stevensville?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This highly rated vacation home rental in Stevensville is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table. Other favorite homes for rent in Stevensville are 240' Private Beachfront @Kent Island Love Point - Great for Families and Relax on Kent Island in a 4 Bedroom Home w/Waterview!.

How many vacation rentals will I find in Stevensville?

With 41 Expedia vacation rentals, you're sure to find just the right place for your Stevensville stay.

What’s there to see and do in Stevensville?

Northern Chesapeake Bay and Chesapeake Bay 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 vacation rental in Stevensville like?

Vacation rentals are private properties where you can stay for several days or longer in Stevensville. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.

Stevensville Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Stevensville vacation rentals

1. Charming Coastal/Country Home w/3 Acres & Sauna!

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

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

5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

6. Cass-N-Reel Luxury Houseboat

7. Family Friendly Cozy 3 Bedroom Duplex

8. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

9. Pool Loft Suite | Bay Access & Beach Passes

10. Cute, Cozy 2-bedroom house near Annapolis with water access

11. Large 2 bedroom house with private parking in a nice neighborhood

12. First Floor Studio Apartment in Historic Chestertown

13. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

14. Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

15. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

16. BAYSIDE BUNGALOW

17. Lower Level Loft - Adorable Studio Apt. Near BWI

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

19. Annapolis Retreat - 7 mins from downtown Annapolis!

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Find vacation rentals that suit your style

Top Stevensville Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

Find out more about Stevensville

Everything you need to know about Stevensville vacation rentals

Stevensville vacation rentals: An excellent choice for every season

How to find incredible deals on Stevensville rentals

Frequently Asked Questions

Can I find a vacation rental in Stevensville?

What's the top vacation rental in Stevensville?

How many vacation rentals will I find in Stevensville?

What’s there to see and do in Stevensville?

What’s a vacation rental in Stevensville like?

Explore a world of travel with Expedia