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Holiday Rentals in Stevensville

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Holiday Rentals in Stevensville

Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (8)
"My husband and I both LOVED this property!!! The houseboat was beautifully decorated, so relaxing and in a great area. We cant wait to go back!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, (3)
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is €1,087
includes taxes & fees
18 Jun - 19 Jun
Waterfront Cottage on the Eastern Shore
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is €343
includes taxes & fees
30 Jun - 1 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (182)
"Prime location!"
Directly Across from Gate One & Steps from the Waterfront
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (15)
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (187)
"Several family members and I went on a fishing trip out of Edgewater. We stayed in this wonderful cottage on the water. The house was immaculate and everything we needed aside from food was provided. The check in and check out were very simple and the host gave us contact information in case we needed anything. The location and overall property could not have been any better. We would definitely stay here again."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (5)
"We had a great time. Children and their parents spent a lot of time in the surprisingly large pool. Some adults chose the hot tub and the most active members of our group were paddleboarding and kayaking in the river. Severl people went hiking at Blackwater, and a few of us just sat on the screened in porch."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, (62)
"This is our second stay and it was just as memorable and lovely as our first stay. Pat and Ken are fantastic hosts. They think of everything! They are super responsive when you have questions/issues. They also let you know about things going on in the community so that you can join if you wish. The house itself is perfect for us. It's very well and generously stocked. Having a washer and dryer on site is a life saver when you travel by plane. I would highly recommend the Firefly Cottage if you...
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is €734
includes taxes & fees
10 Jul - 11 Jul
Charming Annapolis WaterVIEW Home
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (106)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (25)
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, (6)
"This location was extremely clean and perfect for a weekend get away. It’s located not even 2 miles from downtown Annapolis. 10/10 would recommend"
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (40)
"Property and home were in excellent condition. Home made us feel welcome and secure. Host provides extras that make your stay convenient. Close to the restaurants and ice cream shop that serves Hershey ice cream. Love the people and neighborhood."
The Blue Crab Beach House - Free beach passes
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (62)
"My husband and I were traveling to Annapolis for a family reunion with our one year old grandchild. Our hosts, Beth and Andy went above and beyond to make sure that we had a wonderful stay on their beautiful property. We were treated like family the whole time that we were there. Beth was so helpful when it came to questions or concerns that I had in traveling for the first time with our baby granddaughter. To celebrate my Birthday, we took a boat tour with Captain Andy, which was our...
The price is €479
includes taxes & fees
18 Jun - 19 Jun
Waterfront Oasis of Annapolis Star
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, (9)
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
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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.

Other types of properties in Stevensville you may be interested in

The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (345)
"The Inn is a wonderful place - very nice atmosphere, and excellent attentive service. What I liked best is that it was peaceful. I went for a peaceful get-away - and I especially loved the balmy air, the gentle breezes, the gardens, and the birds. Heard and saw so many wonderful birds! And you can meander around the surrounding lanes, and end up down by the water. All so nice!"
The price is €282
includes taxes & fees
7 Jul - 8 Jul
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (69)
"Quiet and beautiful. The staff was very professional and friendly. I felt like I was home. Looking forward to my next visit!!!"
The price is €278
includes taxes & fees
19 Jun - 20 Jun
Kent Island Resort
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
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.

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, apart-hotels, 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 €343 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?

Pool and Bay Views on wrap around deck in Kent Island: This highly rated holiday home rental in Stevensville offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. Other favourite homes for rent in Stevensville are Waterfront Cottage on the Eastern Shore and Relax on Kent Island in 3 Bedroom Home w/Waterview.

How many holiday rentals will I find in Stevensville?

With 35 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?

Matapeake State Park and Love Point State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Paul Reed Smith Guitars. Sandy Point Beach and Chesapeake Bay Environmental Center are a couple of places you'll find in the wider area.

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.

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