Photo by Jennifer Crim

Stevensville Holiday Rentals

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Holiday Rentals in Stevensville

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$391
includes taxes & fees
26 Nov - 27 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.6 out of 10, Exceptional, (20)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Circa 1700 Chesapeake Colonial home on the National Register.
9.8 out of 10, Exceptional, (49)
"We very much enjoyed our stay, relishing the peace and quiet of the property as an offset to our busy wedding week. The house was spacious and well outfitted, and we all enjoyed downtime in the pool. Glen was very helpful at answering all of our questions. We left the galley stairs to the young adults traveling with us. :)"
Circa 1700 Chesapeake Colonial home on the National Register.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (18)
"Great location, great host! "
The price is AU$1,393
includes taxes & fees
3 Dec - 4 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (35)
"The groomsmen and their families attending my daughter's nearby wedding stayed at this spectacular property. I heard nothing but high praise for its beauty, amenities, and comfort. So glad this all worked out for the dates we needed it for!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (12)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (100)
"We absolutely loved staying in this property. It’s comfortable, charming and so well appointed. It’s situated in a great location, within walking distance of all the special things Annapolis has to offer. The host was so easy to communicate with, and we really appreciate that she shares this beautiful home. We will’s definitely be back!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (32)
"We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (71)
"We had an amazing time! Beth and Andy are wonderful hosts! We are looking forward to another stay!"
The price is AU$689
includes taxes & fees
30 Nov - 1 Dec
Waterfront Oasis of Annapolis Star
USNA Quintessential Charm ~ Downtown Annapolis.
9.8 out of 10, Exceptional, (6)
"Limited living room seating for family of 5"
USNA Quintessential Charm ~ 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.
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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, (367)
"Love this property and Knoxie's is the best"
The price is AU$395
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (89)
"Wonderful stay, charming inn. "
The price is AU$342
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
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.
Beautiful view of the beach with palm trees

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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?

Relax on Kent Island in 3 Bedroom Home w/Waterview: This highly rated holiday 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 that you can cook with friends or family. Another good choice for your trip to Stevensville is Pool and Bay Views on wrap around deck in Kent Island.

How many holiday rentals will I find in Stevensville?

With 36 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.