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Our top choices for Kent Island vacation homes

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is ¥17,230
¥45,851 total
includes taxes & fees
Apr 19 - Apr 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ¥13,941
¥42,196 total
includes taxes & fees
Apr 13 - Apr 14
Charming Coastal/Country Home w/3 Acres & Sauna!

Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
8.0 out of 10, Very Good, (3 reviews)
"Great location! Clean! Parking was very easy!"
United States
Susan P.
The price is ¥159,670
¥193,284 total
includes taxes & fees
Apr 6 - Apr 7
Kent Island Luxary Home W/ Pool and walking distance from the beach

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is ¥39,918
¥67,362 total
includes taxes & fees
Apr 6 - Apr 7
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is ¥21,555
¥52,422 total
includes taxes & fees
Apr 6 - Apr 7
Large 2 bedroom house with private parking in a nice neighborhood

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is ¥27,942
¥58,053 total
includes taxes & fees
Apr 13 - Apr 14
Bayside Cottage steps from Rock Hall Harbor

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ¥27,518
¥77,423 total
includes taxes & fees
Apr 6 - Apr 7
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ¥27,144
¥70,019 total
includes taxes & fees
Apr 6 - Apr 7
Family Beach House: Spacious Deck, Grill & Views

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is ¥18,970
¥59,036 total
includes taxes & fees
Apr 12 - Apr 13
Walk to Beach! King Bed & Free Beach Passes

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is ¥52,691
¥98,504 total
includes taxes & fees
Apr 20 - Apr 21
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.4 out of 10, Exceptional, (14 reviews)
"No complaints"
United States
Shelby B.
The price is ¥9,900
¥17,111 total
includes taxes & fees
Apr 9 - Apr 10
Lower Level Loft - Adorable Studio Apt. Near BWI

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ¥41,099
¥93,996 total
includes taxes & fees
May 3 - May 4
Charming Pet-Friendly Stay - Near Bay & Beaches.

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥31,934
¥47,052 total
includes taxes & fees
Apr 30 - May 1
BAYSIDE BUNGALOW

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (10 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is ¥17,564
¥23,663 total
includes taxes & fees
Apr 8 - Apr 9
Secluded Tiny Pool House -Private Pool -Self Check in

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ¥25,236
¥76,883 total
includes taxes & fees
Apr 6 - Apr 7
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is ¥26,346
¥93,379 total
includes taxes & fees
Apr 13 - Apr 14
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ¥49,498
¥100,113 total
includes taxes & fees
Apr 28 - Apr 29
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (4 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is ¥13,795
¥36,658 total
includes taxes & fees
Apr 13 - Apr 14
Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is ¥31,615
¥82,195 total
includes taxes & fees
Apr 6 - Apr 7
Cute bungalow blocks to Stadium

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ¥31,136
¥89,374 total
includes taxes & fees
Apr 6 - Apr 7
Annapolis Retreat - 7 mins from 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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Top Kent Island Hotel Reviews

Find out more about Kent Island

Kent Island Vacation Homes information

Number of reviews
294
Accommodation
660 Vacation Homes
Lowest Price
¥17,111
Highest Price
¥193,284

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