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Kent Island Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Kent Island Vacation Homes

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

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

10.0 out of 10, Exceptional, (228)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Enjoy the view from this home's deck, overlooking the city street below.

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

9.6 out of 10, Exceptional, (87)
"Great location in quiet neighborhood."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (114)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming townhome with AC and WiFi in delightful Annapolis
Enjoy cooking in this well-equipped kitchen with a refrigerator, dark wood cabinetry, and a window with blinds.

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is CA $62
CA $102 total
includes taxes & fees
Sep 6 - Sep 7
Charming townhome with AC and WiFi in delightful Annapolis
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

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

2.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Heated pool, sandy beach, pier, and playground set punch point apart!
Relax in Adirondack chairs along the serene lakeside, with a boat available for recreation.

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (9)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Pet-Friendly Home on Chester River w/ Dock!
Relax in a spacious, open-plan room with multiple seating areas and large windows offering a view of the outdoors.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

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

9.8 out of 10, Exceptional, (44)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $181
CA $457 total
includes taxes & fees
Aug 27 - Aug 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Bay views with kayaks, bikes, fire pit, crabbing and more
Enjoy cooking and dining in this well-equipped kitchen with appliances and a central island.

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (20)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is CA $260
CA $779 total
includes taxes & fees
Aug 18 - Aug 19
Edgewater/Mayo Gateaway w/ Hot Tub
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Kitchen features a stove, oven, microwave, and large island with seating.

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Enjoy a room with a sliding glass door leading to a balcony offering a water view.

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (17)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave, and dine at the wooden table.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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 Kent Island Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The breakfast was amazing and the restaurant staff made it even better. Al greeted us with a warm smile everyday and the staff were very attentive, making sure our meals and experience was just right. "
Colleen 2-night trip
Posted 10 hours ago
The Westin Annapolis