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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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, (44 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 AED 453
AED 1,152 total
includes taxes & fees
13 Aug - 14 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, (51 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 AED 453
AED 1,149 total
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Outdoor dining

3. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"
United States
Hoi C.
The price is AED 2,567
AED 4,664 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Escape with Pool Nature Lover Paradise
Terrace/patio

4. 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 AED 883
AED 1,869 total
includes taxes & fees
26 Aug - 27 Aug
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Marina

5. Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is AED 791
AED 1,006 total
includes taxes & fees
6 Aug - 7 Aug
Sailboat Experience in Annapolis
Property grounds

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

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is AED 1,030
AED 2,141 total
includes taxes & fees
19 Aug - 20 Aug
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Beach

7. 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, (27 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 433
AED 1,042 total
includes taxes & fees
6 Aug - 7 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

8. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AED 364
AED 583 total
includes taxes & fees
10 Aug - 11 Aug
First Floor Studio Apartment in Historic Chestertown
Dining

9. 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, (15 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 AED 918
AED 1,538 total
includes taxes & fees
6 Aug - 7 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior detail

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AED 661
AED 1,020 total
includes taxes & fees
18 Aug - 19 Aug
BAYSIDE BUNGALOW
Outdoor pool, a heated pool

11. 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 AED 900
AED 1,700 total
includes taxes & fees
1 Sep - 2 Sep
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 709
AED 1,750 total
includes taxes & fees
10 Aug - 11 Aug
Pool Loft Suite | Bay Access & Beach Passes
Smart TV

13. 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 AED 643
AED 1,335 total
includes taxes & fees
1 Sep - 2 Sep
Bayside Cottage steps from Rock Hall Harbor
Marina

14. 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 AED 633
AED 1,781 total
includes taxes & fees
11 Aug - 12 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Interior

15. 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 AED 540
AED 1,256 total
includes taxes & fees
1 Sep - 2 Sep
Large 2 bedroom house with private parking in a nice neighborhood
Coffee/tea maker, fridge, microwave, oven

16. 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, (18 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AED 314
AED 852 total
includes taxes & fees
17 Aug - 18 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Coffee/tea maker, fridge, microwave, oven

17. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (11 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AED 973
AED 2,403 total
includes taxes & fees
1 Sep - 2 Sep
Renovated Bungalow | Walk to Beach | Dog-Friendly
House (3 Bedrooms) | Interior

18. Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is AED 1,315
AED 1,678 total
includes taxes & fees
12 Aug - 13 Aug
Waterfront Home on Marley Creek!
Smart TV, stereo

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

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (18 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is AED 239
AED 406 total
includes taxes & fees
12 Aug - 13 Aug
Lower Level Loft - Adorable Studio Apt. Near BWI
Interior

20. 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 AED 657
AED 2,006 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"clean, extremely helpful staff, exactly as described"
Sasha 3-night trip
Posted 4 hours ago
Historic Inns of Annapolis

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 Circa 1700 Chesapeake Colonial home on the National Register. and 240' Private Beachfront @Kent Island Love Point - Great for Families.

How many vacation rentals will I find in Stevensville?

With 40 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.