Stevensville Vacation Rentals from $345: Search Short-Term Rentals

Q: What's the top vacation rental in Stevensville?

Private Pool & Stunning Bay Views on Kent Island : This highly rated vacation home rental in Stevensville offers a fireplace, a balcony, and a barbecue grill 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. You can relax into your vacation with a garden and a selection of games. Other favorite homes for rent in Stevensville are Circa 1700 Chesapeake Colonial home on the National Register. and Relax on Kent Island in a 4 Bedroom Home w/Waterview! .

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Our top choices for Stevensville vacation rentals

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

Stevensville

Handy M.

$332 nightly

Jun 29 - Jun 30

Total with taxes and fees

Waterfront Escape with Pool Nature Lover Paradise

Stevensville

Jeffrey T.

$1,144 nightly

Jun 29 - Jun 30

Total with taxes and fees

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

Stevensville

"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."

Brian

$318 nightly

Jun 29 - Jun 30

Total with taxes and fees

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

Arnold

Chris A.

$388 nightly

Jun 30 - Jul 1

Total with taxes and fees

Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

$349 nightly

Jun 22 - Jun 23

Total with taxes and fees

First Floor Studio Apartment in Historic Chestertown

Chestertown

lesia k.

$144 nightly

Jun 22 - Jun 23

Total with taxes and fees

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

Cambridge

Jill C.

$566 nightly

Jun 23 - Jun 24

Total with taxes and fees

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

Grasonville

Robin

$395 nightly

Jun 22 - Jun 23

Total with taxes and fees

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Top Stevensville Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"The room was small, but very nice for me (a single traveler). Bathroom was small and not well lit, but it was still nice. The bed was really comfortable! I enjoyed my stay in this historical inn."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"It was our first time in the area so this hotel made the experience great all around. Everything was clean, the food was super good too! We ate breakfast two days in a row and ordered dinner and all meals were hot, fresh and delicious. The area where the hotel is at is convenient but it seems the gps isn’t the best for getting around as our transportation from the airport got lost and we had uber drivers get lost as well, but we walked across the street to the mall twice and it’s fairly quick and easy to get to and there are a good amount of restaurants near by"

Chesapeake Houseboat Getaway on Kent Island, Maryland

10/10 Excellent

"Beautiful home on the water! Everything was very clean and Julia was amazing! She answered my questions instantly and made the whole experience easy. We walked to the local spot on the water and had a great time hanging out with the locals, great food and water views. Julia offered a ton of options to choose from whether you’re just hanging out for a night or two and need a good spot to get a bite to eat or other cool places to go. We will definitely be back!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

10/10 Excellent

"This place was absolutely amazing! The backyard and the 3 seasons room is so adorable and unique. This has been my favorite vrbo we have stayed at yet. It’s decorated so nicely which truly makes it homey. Our dogs absolutely loved the place too! Thank you for having such a lovely place and letting us stay:)"

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10/10 Excellent

"Beautiful property, very comfortable place to stay for our party of eight. Lou and Shelly are great hosts! One note to future renters: there is no automatic dishwasher, so be prepared to wash and dry. No problem for us but could be an unwelcome surprise for others."

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 $345 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.

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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?

Private Pool & Stunning Bay Views on Kent Island: This highly rated vacation home rental in Stevensville offers a fireplace, a balcony, and a barbecue grill 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. You can relax into your vacation with a garden and a selection of games. Other favorite homes for rent in Stevensville are Circa 1700 Chesapeake Colonial home on the National Register. and Relax on Kent Island in a 4 Bedroom Home w/Waterview!.

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.

Stevensville Vacation Rentals

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Check prices for these dates

Our top choices for Stevensville vacation rentals

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

Waterfront Escape with Pool Nature Lover Paradise

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

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

Newly restored apartment in the heart of Chestertown

First Floor Studio Apartment in Historic Chestertown

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

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

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

BAYSIDE BUNGALOW

RELAX- Eastern Shore Creek Home - 6 Guests

Fabulous 5-bedroom house with AC in charming Annapolis

Family Home on Mayo Peninsula | Deck | Sleeps 10

Plum Point Cottage #17

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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

Sunset Cottage - West River Access and Views!

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Large 2 bedroom house with private parking in a nice neighborhood

Find vacation rentals that suit your style

Top Stevensville Hotel Reviews

Historic Inns of Annapolis

Find out more about Stevensville

Explore a world of travel with Expedia

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