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Holiday Homes in Kent Island

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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Holiday Homes in Kent Island

Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (25)
"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, (227)
"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!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"We had a great time! The house was really nice, very comfortable and clean. It had everything that you needed. I really liked that everything was controlled by alexa even the window blinds. I definitely recommend staying here and I definitely will be returning. "
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
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, (112)
"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 Coastal/Country Home w/3 Acres & Sauna!❤️
Overlooking the marina, the city skyline reflects off the calm water, offering a serene urban experience.

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is NZ$585
includes taxes & fees
3 Aug - 4 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Relax by the pool surrounded by lush greenery and vintage bicycles.

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.6 out of 10, Exceptional, (24)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
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)
"We really enjoyed this property. It had everything we would want and plenty of space. It was very clean and quiet. The water, fire-pit, porch and living spaces were wonderful for a nice long-weekend get-away!"
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Cozy Annapolis Cottage
Relax on the outdoor deck surrounded by lush greenery and trees, featuring a sofa set, wicker chair, and small table.

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (11)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Enjoy cooking in this well-equipped kitchen with a dishwasher, sink, and range hood.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (14)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
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

Rising Sun Bay View Cottage
Charming Historic Annapolis Home With Two Off-street Parking Places!
Staircase leads to a warm and inviting interior with a fireplace and wooden door.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (188)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Stroll up to the charming entrance, where a brick pathway leads to a cozy home with a red door and inviting porch.

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

10.0 out of 10, Exceptional, (44)
"This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again. "
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Spacious 4 Bedroom Home w/ Hot Tub
Fridge, microwave, oven, stovetop

Spacious 4 Bedroom Home w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is NZ$921
includes taxes & fees
23 July - 24 July
Spacious 4 Bedroom Home w/ 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 NZ$516
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview
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, (64)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (5)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Relax in a serene sauna with a wooden bench and natural ambiance.

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (41)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is NZ$498
includes taxes & fees
27 July - 28 July
BAYSIDE BUNGALOW
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed at the Historic Inns of Annapolis - Governor Calvert House. The front desk receptionist was friendly and helpful. Check in was easy and efficient. Valet parked the car and due to being centrally located, we didn't use the car for the two days we were in Annapolis. The room was clean and the bed was comfortable. Very quiet. We would definitely stay here again! "
Mary 2-night trip
Posted 2 days ago
Historic Inns of Annapolis