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

Stevensville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

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
$284 nightly
The price is $307
Aug 13 - Aug 14
Total with taxes and fees
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
$283 nightly
The price is $305
Aug 11 - Aug 12
Total with taxes and fees
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.
$1,198 nightly
The price is $1,270
Aug 30 - Aug 31
Total with taxes and fees
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.
$304 nightly
The price is $347
Aug 9 - Aug 10
Total with taxes and fees
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)
$269 nightly
The price is $274
Aug 6 - Aug 7
Total with taxes and fees
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
$370 nightly
The price is $421
Aug 9 - Aug 10
Total with taxes and fees
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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$257 nightly
The price is $284
Aug 6 - Aug 7
Total with taxes and fees
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.
$144 nightly
The price is $159
Aug 10 - Aug 11
Total with taxes and fees
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
$395 nightly
The price is $419
Aug 6 - Aug 7
Total with taxes and fees
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.
$262 nightly
The price is $278
Aug 22 - Aug 23
Total with taxes and fees
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
$406 nightly
The price is $463
Sep 1 - Sep 2
Total with taxes and fees
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.
$418 nightly
The price is $476
Aug 10 - Aug 11
Total with taxes and fees
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.
$343 nightly
The price is $364
Aug 10 - Aug 11
Total with taxes and fees
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
$425 nightly
The price is $485
Aug 10 - Aug 11
Total with taxes and fees
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.
$300 nightly
The price is $342
Sep 1 - Sep 2
Total with taxes and fees
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.
$204 nightly
The price is $232
Aug 17 - Aug 18
Total with taxes and fees
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.
$548 nightly
The price is $625
Sep 1 - Sep 2
Total with taxes and fees
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
$401 nightly
The price is $457
Aug 12 - Aug 13
Total with taxes and fees
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
$97 nightly
The price is $111
Aug 12 - Aug 13
Total with taxes and fees
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.
$486 nightly
The price is $554
Aug 31 - Sep 1
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stevensville Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Convient location. Nice amenities including dog friendly, hugh pool. Full service restaurant. Shuttle that takes you around town to downtown and surrounding 5 mile radius which was a nice bonus."
Dixie 3-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Annapolis

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 $232 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.

Explore a world of travel with Expedia

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.