Photo by Jennifer Crim

Kent Island Holiday Rentals

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Holiday Rentals in Kent Island

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (23)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is AU$386
includes taxes & fees
13 Mar - 14 Mar
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
7.4 out of 10, Good, (3)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is AU$438
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in 3 Bedroom Home w/Waterview

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
The price is AU$1,458
includes taxes & fees
12 Mar - 13 Mar
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (37)
"We can’t express how perfect our stay was. This property is perfect! And the details added were just beyond. We explained that we were using the home for a Moms weekend away to read and relax and we were greeted with an amazing table scape and chocolates! No one wanted to leave. The level of comfort achieved at this property was fantastic! Thank you!!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6

Beautiful Chesapeake Bay Views -pet friendly

9.6 out of 10, Exceptional, (114)
"The home accomodated"
Beautiful Chesapeake Bay Views -pet friendly

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (208)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (68)
"This is a great location The house is clean and updated. We enjoyed and would stay here again."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (22)
"The property was beautiful, clean and comfortable with an amazing view. Will definitely be back."
Cass-N-Reel Luxury Houseboat

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (50)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (15)
"First time in Annapolis to watch East Carolina win the Military Bowl and tour the Naval Academy.Great location, cute, clean, and comfortable place in a fun town with lots of great restaurants and bars."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
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 Kent Island you may be interested in

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (375)
"Great spot!"
The price is AU$355
includes taxes & fees
16 Mar - 17 Mar
The Inn at Chesapeake Bay Beach Club

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (99)
"This is a really special property. A girlfriend and I got away for a night without the kids and found the historic property and the sprawling estate where it sits to be a perfect escape. The service was very friendly and attentive, the rooms lovely, the bar open at 12pm, and dinner delicious. We’ll definitely be back. "
The price is AU$407
includes taxes & fees
16 Mar - 17 Mar
Kent Island Resort

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
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.