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Holiday Homes in Kent Island

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Our top choices for Kent Island holiday 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)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$458
includes taxes & fees
5 Jan - 6 Jan 2026
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, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$474
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Coastal/Country Home w/3 Acres & Sauna!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$553
includes taxes & fees
11 Jan - 12 Jan 2026
Walk to Beach! King Bed & Free Beach Passes

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is NZ$763
includes taxes & fees
5 Jan - 6 Jan 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is NZ$638
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!

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, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$681
includes taxes & fees
30 Dec - 31 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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)
"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 NZ$905
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (6)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is NZ$964
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Pet-Friendly Stay - Near Bay & Beaches.

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$518
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport
Pasadena
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
The price is NZ$272
includes taxes & fees
6 Jan - 7 Jan 2026
Modern New Suite Close to US Capital and BWI Airport

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is NZ$1,061
includes taxes & fees
20 Jan - 21 Jan 2026
Neptune by the Water - Pet Friendly Fenced Yard

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)
"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 NZ$707
includes taxes & fees
30 Dec - 31 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is NZ$1,022
includes taxes & fees
28 Jan - 29 Jan 2026
Holly Hill Haven - Sleeps 10

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, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is NZ$541
includes taxes & fees
4 Jan - 5 Jan 2026
Large 2 bedroom house with private parking in a nice neighborhood

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Glen Burnie
8.0 out of 10, Very good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is NZ$215
includes taxes & fees
30 Dec - 31 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$776
includes taxes & fees
27 Jan - 28 Jan 2026
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is NZ$598
includes taxes & fees
1 Jan - 2 Jan 2026
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$906
includes taxes & fees
19 Jan - 20 Jan 2026
Annapolis Retreat - 7 mins from downtown Annapolis!

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (20)
"The place stay was above and beyond, after arriving at the location I was more than surprised to see the size, amenities, and accommodations available."
United States
Matthew O.
The price is NZ$555
includes taxes & fees
5 Jan - 6 Jan 2026
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

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
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$917
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 Holiday Homes information

Number of reviews
357
Accommodation
708 Holiday Homes
Lowest Price
NZ$215
Highest Price
NZ$1,061

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