Stevensville Holiday Rentals

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Our top choices for Stevensville holiday rentals

9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$386
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$396
includes taxes & fees
22 Jan - 23 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AU$239
includes taxes & fees
29 Jan - 30 Jan
First Floor Studio Apartment in Historic Chestertown
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$426
includes taxes & fees
22 Jan - 23 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is AU$538
includes taxes & fees
25 Jan - 26 Jan
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (8 reviews)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
HGTV quality, private guest suite, country getaway with hot tub & fire pit
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$611
includes taxes & fees
2 Feb - 3 Feb
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is AU$427
includes taxes & fees
1 Feb - 2 Feb
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$459
includes taxes & fees
22 Jan - 23 Jan
Walk to Beach! King Bed & Free Beach Passes
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
The price is AU$541
includes taxes & fees
26 Jan - 27 Jan
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$412
includes taxes & fees
25 Jan - 26 Jan
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (14 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is AU$788
includes taxes & fees
27 Jan - 28 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 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 AU$565
includes taxes & fees
25 Jan - 26 Jan
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$580
includes taxes & fees
22 Jan - 23 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is AU$457
includes taxes & fees
25 Jan - 26 Jan
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$785
includes taxes & fees
25 Jan - 26 Jan
Annapolis Retreat - 7 mins from downtown 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 AU$701
includes taxes & fees
25 Jan - 26 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
The price is AU$4,518
includes taxes & fees
23 Jan - 24 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
8.6 out of 10, Excellent, (10 reviews)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is AU$188
includes taxes & fees
22 Jan - 23 Jan
Secluded Tiny Pool House -Private Pool -Self Check in
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$596
includes taxes & fees
25 Jan - 26 Jan
Waterfront Oasis of Annapolis Star
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stevensville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Stevensville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stevensville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stevensville holiday rentals we have selected for you start as low as AU$386 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Stevensville rentals

At Expedia, we put the best Stevensville holiday 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 holiday.

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 holiday rental in Stevensville?

Yes, there are holiday rentals in Stevensville close to Paul Reed Smith Guitars, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stevensville has a good selection of restaurants. Make sure you have time to check out the spas and shopping during your trip.

What are some of the best holiday rentals that Stevensville has to offer?

240' Private Beachfront @Kent Island Love Point - Great for Families: This highly rated holiday home rental in Stevensville is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Other favourite homes for rent in Stevensville are Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. and Relax on Kent Island in a 4 Bedroom Home w/Waterview!.

How many holiday rentals will I find in Stevensville?

With 38 Expedia holiday rentals, you're guaranteed 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 holiday rental in Stevensville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stevensville. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip.