Stevensville Vacation Rentals

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Our top choices for Stevensville vacation rentals

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, (44 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
$240 nightly
The price is $254
May 17 - May 18
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
$329 nightly
The price is $349
May 26 - May 27
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
8.0 out of 10, Very Good, (3 reviews)
"Great location! Clean! Parking was very easy!"
United States
Susan P.
$1,142 nightly
The price is $1,211
May 18 - May 19
Total with taxes and fees
Kent Island Luxary Home W/ Pool and walking distance from the beach

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
$339 nightly
The price is $359
May 17 - May 18
Total with taxes and fees
40' Bristol sailboat with spectacular views

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
May 18 - May 19
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$501 nightly
The price is $531
May 18 - May 19
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$259 nightly
The price is $275
May 17 - May 18
Total with taxes and fees
BAYSIDE BUNGALOW

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, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
$395 nightly
The price is $419
May 18 - May 19
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$597 nightly
The price is $680
Jun 1 - Jun 2
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$255 nightly
The price is $281
May 18 - May 19
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
May 18 - May 19
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$341 nightly
The price is $361
Jun 2 - Jun 3
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor

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)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
$274 nightly
The price is $312
Jun 7 - Jun 8
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.0 out of 10, Wonderful, (11 reviews)
"THE PERFECT WATERSIDE GETAWAY!!! The Hideaway Spot is a true GEM of a location/property for "
United States
Karen M.
$429 nightly
The price is $489
May 18 - May 19
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$407 nightly
The price is $464
Jun 4 - Jun 5
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
$464 nightly
The price is $529
May 17 - May 18
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.

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
$425 nightly
The price is $485
May 24 - May 25
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
$379 nightly
The price is $433
May 17 - May 18
Total with taxes and fees
3-Bedroom Beach Home w/ Backyard

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
$581 nightly
The price is $662
Jun 7 - Jun 8
Total with taxes and fees
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

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.
$507 nightly
The price is $578
Jun 8 - Jun 9
Total with taxes and fees
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

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 $254 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?

NEW! Charming Farm House in Historic Kent Island : This highly rated vacation home rental in Stevensville is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease 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 Relax on Kent Island in a 4 Bedroom Home w/Waterview! and Circa 1700 Chesapeake Colonial home on the National Register..

How many vacation rentals will I find in Stevensville?

With 38 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.