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Compare 649 Vacation Homes in Kent Island with updated reviews, rates, and availability.

Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, (1)
"The house was exactly as promised! We were very happy with the accommodations!"
The price is $423
$1,012 total
includes taxes & fees
Jun 30 - Jul 1
Caribbean Pool Home <1 mile from Matapeake Beach!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (6)
"Overall the home is beautiful. There is a gorgeous mostly well stocked kitchen and 3 bedrooms with beds for couples. One of the king beds listed is a pull out couch in the pool house. The biggest con of this place is that there are no blackout curtains or anything to block the sun in the bedroom so for our June visit the rooms were very bright at 5:45AM. We also had to go out and buy some of our own things that you'd think would be included (garbage bags). Other than that its a beautiful home...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (19)
"Would definitely stay here again. When we arrived, the space was clean, cozy, and inviting. Big enough for 2 people for an overnight stay as we were staying here for a local wedding. "
The price is $175
$272 total
includes taxes & fees
Jun 25 - Jun 26
BAYSIDE BUNGALOW
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Miller's Cottage
10.0 out of 10, Exceptional, (25)
"We really enjoyed our stay at Miller's Cottage. It was in the perfect quaint neighborhood away from the big city life. Just the right size for 3 adults. Would definitely recommend!"
Miller's Cottage
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
10.0 out of 10, Exceptional, (8)
"Loved our stay! House is clean and well maintained. Loved the location as it is close to stores and about 15 minutes from the mall. Sue was a great host and very responsive. Would stay here again!"
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
The price is $239
$467 total
includes taxes & fees
Jun 30 - Jul 1
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
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
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.
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
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, (9)
"This place was just perfect for my husband and I. The location was great and the neighborhood was safe. Thanks for a wonderful week!!"
The price is $78
$121 total
includes taxes & fees
Jun 25 - Jun 26
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Super close to all downtown amenities. Would definitely return."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Cozy suite Located in Presidents Hill
10.0 out of 10, Exceptional, (8)
"Loved the small touches of cookies, snacks, gifts- all super welcoming and homey- thank you!"
Cozy suite Located in Presidents Hill
200 steps to the beach!
10.0 out of 10, Exceptional, (77)
"Cute cottage very close to the beach. We had everything that we needed for our mini vacation. Very clean and well taken care of cottage."
200 steps to the beach!
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
10.0 out of 10, Exceptional, (9)
"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Historic Annapolis Home!
10.0 out of 10, Exceptional, (2)
"We absolutely adored this house in the heart of Annapolis! The decor was stylish and welcoming, making us feel right at home. The bedrooms were incredibly spacious - we had plenty of room to spread out. But what really made our stay special was the location. We were within walking distance to all the best spots in Annapolis. Our host, Sarah, was fantastic. Her communication was top-notch from start to finish. She made sure we had everything we needed for a comfortable stay. We can't recommend...
Historic Annapolis Home!
Waterfront newly-renovated home with deep water private pier minutes to Annapolis
10.0 out of 10, Exceptional, (1)
Waterfront newly-renovated home with deep water private pier minutes to Annapolis
Art's Dist
Art's Dist
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (183)
"This house is perfect for stayiing in the historic distict of Annapolis. Very comfortable and clean. One and one half baths, a private patio, and the best part is the off street parking with a private garage; very hard to find in this beautiful area. John, the manager was so helpful and answered all my questions. If ever in Annapolis again, we will definately stay here."
Directly Across from Gate One & Steps from the Waterfront
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
Walk to Everything House
10.0 out of 10, Exceptional, (64)
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
Walk to Everything House
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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 property types in Kent Island

Kent Island Vacation Homes information

Number of reviews
479
Accommodation
649 Vacation Homes
Lowest Price
$78
Highest Price
$423

Recent reviews of Kent Island hotels
Expedia verified reviews