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Kent Island Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Kent Island

Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Holiday Home in Stevensville

10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Holiday Home in stevensville

10.0 out of 10, Exceptional, (196)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Holiday Home in Chester

10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (42)
"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 HK$572
HK$1,977 total
includes taxes & fees
3 Dec - 4 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior
Circa 1700 Chesapeake Colonial home on the National Register.

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (57)
"What a stunning place, we were delighted by this 300 year old property, the view was incredible. "
United States
Karen N.
Circa 1700 Chesapeake Colonial home on the National Register.
Interior
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

10.0 out of 10, Exceptional, (57)
"A comfortable , impeccably styled stay where every detail was thoughtfully curated by wonderful owners.Down to the water bowl for the dogs."
United States
Marianne R.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Marina
Chesapeake Houseboat Getaway on Kent Island, Maryland

Houseboat in Stevensville

9.8 out of 10, Exceptional, (45)
"Just perfect for a 4 night stay."
United States
Lyn
Chesapeake Houseboat Getaway on Kent Island, Maryland
Fridge, microwave, oven, stovetop
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (44)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Interior
40' Bristol sailboat with spectacular views

Houseboat in Stevensville

2.0 star property
40' Bristol sailboat with spectacular views
Property grounds
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Holiday Home in Pasadena

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Holiday Home in Historic District

10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Holiday Home in Arnold

9.4 out of 10, Exceptional, (33)
"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 HK$1,016
HK$2,525 total
includes taxes & fees
3 Dec - 4 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in Cambridge

10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Holiday Home in Tracys Landing

9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is HK$2,804
HK$5,176 total
includes taxes & fees
3 Dec - 4 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$771
HK$1,237 total
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Holiday Home in 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 HK$701
HK$976 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Evening bar staff was exceptional, as was the crew at the check-in desk. Excellent recommendations for places to eat. This hotel is within walking distance of everything we wanted to see and do. So much history here, cool stores, venues, and not far from the bay."
Jan Michael 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown

Find out more about Kent Island

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