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 lighthouse with a white exterior, a balcony, and a metal roof.

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

Stevensville

Michael V.

AED 1,149 total

includes taxes & fees

9 Nov - 10 Nov

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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

Stevensville

Anthony P.

AED 1,340 total

includes taxes & fees

23 Nov - 24 Nov

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.

AED 4,626 total

includes taxes & fees

1 Dec - 2 Dec

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.

AED 4,620 total

includes taxes & fees

18 Nov - 19 Nov

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

AED 3,679 total

includes taxes & fees

6 Nov - 7 Nov

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

6. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

AED 947 total

includes taxes & fees

12 Nov - 13 Nov

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

7. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

AED 1,141 total

includes taxes & fees

5 Nov - 6 Nov

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

AED 1,059 total

includes taxes & fees

18 Nov - 19 Nov

Stylish kitchen with open layout and island seating

9. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

AED 1,690 total

includes taxes & fees

5 Nov - 6 Nov

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.

AED 770 total

includes taxes & fees

29 Nov - 30 Nov

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

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

Arnold

Linda B.

AED 1,151 total

includes taxes & fees

5 Nov - 6 Nov

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.

AED 552 total

includes taxes & fees

5 Nov - 6 Nov

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Ryan C.

AED 1,692 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

AED 1,603 total

includes taxes & fees

5 Nov - 6 Nov

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

16. BAYSIDE BUNGALOW

Rock Hall

Diane V.

AED 1,105 total

includes taxes & fees

5 Nov - 6 Nov

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

AED 348 total

includes taxes & fees

17 Nov - 18 Nov

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.

AED 2,058 total

includes taxes & fees

8 Nov - 9 Nov

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.

AED 2,039 total

includes taxes & fees

10 Nov - 11 Nov

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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.

AED 1,935 total

includes taxes & fees

18 Nov - 19 Nov

View all properties

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

Two Adirondack chairs facing a calm body of water with a clear sky above.

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 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

A patio with outdoor seating, overlooking a marina with boats.

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 spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Robert

A marina with boats docked at wooden piers, surrounded by greenery.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

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 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 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 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

A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Excellent

MARA

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

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

Change your mind

Treat yourself

Be picky

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

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?