Kent Island Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Kent Island holiday rentals

Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"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 HK$589
HK$1,964 total
includes taxes & fees
21 Jan - 22 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"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$497
HK$1,890 total
includes taxes & fees
20 Jan - 21 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$772
HK$1,238 total
includes taxes & fees
20 Jan - 21 Jan
First Floor Studio Apartment in Historic Chestertown
Beach

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is HK$918
HK$2,236 total
includes taxes & fees
20 Jan - 21 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17 reviews)
"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 HK$523
HK$2,386 total
includes taxes & fees
20 Jan - 21 Jan
Walk to Beach! King Bed & Free Beach Passes
Fridge, microwave, oven, stovetop

Holiday Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is HK$1,228
HK$2,905 total
includes taxes & fees
22 Jan - 23 Jan
Beautiful Waterfront Retreat in Cambridge!
Exterior detail

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,123
HK$2,306 total
includes taxes & fees
20 Jan - 21 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Fridge, microwave, dishwasher, coffee/tea maker

Holiday Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (8 reviews)
"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 HK$1,537
HK$3,480 total
includes taxes & fees
26 Jan - 27 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Outdoor dining

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$695
HK$3,083 total
includes taxes & fees
21 Jan - 22 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior detail

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,559
HK$2,355 total
includes taxes & fees
20 Jan - 21 Jan
BAYSIDE BUNGALOW
Dining

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 HK$1,949
HK$3,281 total
includes taxes & fees
20 Jan - 21 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
1 bedroom, desk, free WiFi, bed sheets

Holiday Home in South Gate

Lower Level Loft - Adorable Studio Apt. Near BWI
9.4 out of 10, Exceptional, (13 reviews)
"No complaints"
United States
Shelby B.
The price is HK$463
HK$928 total
includes taxes & fees
29 Jan - 30 Jan
Lower Level Loft - Adorable Studio Apt. Near BWI
Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,614
HK$3,227 total
includes taxes & fees
20 Jan - 21 Jan
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$975
HK$3,049 total
includes taxes & fees
20 Jan - 21 Jan
Luxury Pool Loft sleeps 4
Marina

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is HK$904
HK$2,364 total
includes taxes & fees
20 Jan - 21 Jan
Cozy 2br home w/ parking in downtown Annapolis
Smart TV

Holiday Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is HK$2,046
HK$4,119 total
includes taxes & fees
21 Jan - 22 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, fireplace

Holiday Home in Glen Burnie

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very good, (2 reviews)
"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$702
HK$978 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Outdoor pool

Holiday Home in Glen Burnie

Secluded Tiny Pool House -Private Pool -Self Check in
8.6 out of 10, Excellent, (10 reviews)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is HK$695
HK$970 total
includes taxes & fees
20 Jan - 21 Jan
Secluded Tiny Pool House -Private Pool -Self Check in
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 HK$1,344
HK$3,781 total
includes taxes & fees
20 Jan - 21 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Property grounds

Holiday Home in Herald Harbor

Cute, Cozy 2-bedroom house in near Annapolis with water access
2.0 star property
The price is HK$636
HK$1,783 total
includes taxes & fees
20 Jan - 21 Jan
Cute, Cozy 2-bedroom house in near Annapolis with water access
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Nice staff. Clean room"
Carol 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Kent Island

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