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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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Stevensville vacation rentals

Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is SAR 399
SAR 1,136 total
includes taxes & fees
19 Aug - 20 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (53 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is SAR 500
SAR 1,260 total
includes taxes & fees
24 Aug - 25 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

3. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is SAR 3,032
SAR 5,244 total
includes taxes & fees
15 Sep - 16 Sep
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
On the beach, sun loungers, beach towels

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

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (76 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is SAR 3,032
SAR 5,244 total
includes taxes & fees
15 Sep - 16 Sep
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Outdoor dining

5. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is SAR 2,362
SAR 4,454 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise
Terrace/patio

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

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Chris A.
The price is SAR 741
SAR 1,650 total
includes taxes & fees
24 Aug - 25 Aug
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Dining

7. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is SAR 939
SAR 1,592 total
includes taxes & fees
24 Aug - 25 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"What a great apartment and location for a getaway. Had everything we needed and so convenient! I will absolutely stay here again."
United States
Charlotte M.
The price is SAR 466
SAR 1,107 total
includes taxes & fees
23 Aug - 24 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

9. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is SAR 372
SAR 596 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Terrace/patio

10. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is SAR 727
SAR 1,487 total
includes taxes & fees
18 Aug - 19 Aug
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is SAR 723
SAR 1,834 total
includes taxes & fees
18 Aug - 19 Aug
Pool Loft Suite | Bay Access & Beach Passes
Marina

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is SAR 719
SAR 1,915 total
includes taxes & fees
18 Aug - 19 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Exterior detail

13. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is SAR 676
SAR 1,086 total
includes taxes & fees
15 Sep - 16 Sep
BAYSIDE BUNGALOW
Interior

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

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is SAR 582
SAR 1,340 total
includes taxes & fees
8 Sep - 9 Sep
Large 2 bedroom house with private parking in a nice neighborhood
Interior

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is SAR 695
SAR 2,050 total
includes taxes & fees
13 Sep - 14 Sep
Annapolis Retreat - 7 mins from downtown Annapolis!
Coffee/tea maker, fridge, microwave, oven

16. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Smart TV

17. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is SAR 852
SAR 1,600 total
includes taxes & fees
24 Aug - 25 Aug
Bayside Cottage steps from Rock Hall Harbor
Coffee/tea maker, fridge, microwave, oven

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (19 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is SAR 321
SAR 880 total
includes taxes & fees
24 Aug - 25 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Exterior detail

19. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is SAR 449
SAR 1,197 total
includes taxes & fees
18 Aug - 19 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Living area

20. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is SAR 925
SAR 2,429 total
includes taxes & fees
19 Aug - 20 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
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.
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Top Stevensville Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"We had a great time and will stay again!"
Julia 2-night trip
Posted 3 hours ago
St Michaels Inn

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?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: This highly rated vacation home rental in Stevensville offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Stevensville are 240' Private Beachfront @Kent Island Love Point - Great for Families and Waterfront Escape with Pool Nature Lover Paradise.

How many vacation rentals will I find in Stevensville?

With 39 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.