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Stevensville Holiday Rentals

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Our top choices for Stevensville holiday rentals

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
9.8 out of 10, Exceptional, (42)
"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 NZ$387
includes taxes & fees
14 Dec - 15 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (57)
"What a stunning place, we were delighted by this 300 year old property, the view was incredible. "
United States
Karen N.
Circa 1700 Chesapeake Colonial home on the National Register.
9.8 out of 10, Exceptional, (44)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (45)
"Just perfect for a 4 night stay."
United States
Lyn
Chesapeake Houseboat Getaway on Kent Island, Maryland
2.0 star property
40' Bristol sailboat with spectacular views
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$274
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$520
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is NZ$1,145
includes taxes & fees
15 Dec - 16 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is NZ$600
includes taxes & fees
15 Dec - 16 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Houseboat in Grasonville

Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
9.6 out of 10, Exceptional, (125)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is NZ$1,999
includes taxes & fees
14 Dec - 15 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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 favorite 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 depends 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 NZ$274 per night. Entering your travel dates in the search wizard you might find 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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This highly rated holiday home rental in Stevensville is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table. Other favourite homes for rent in Stevensville are 240' Private Beachfront @Kent Island Love Point - Great for Large Groups and Circa 1700 Chesapeake Colonial home on the National Register..

How many holiday rentals will I find in Stevensville?

With 39 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.