A coastal town with a marina, a bridge, and a highway.

Kent Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Kent Island vacation rentals

Exterior

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, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is ￥14,176
￥43,273 total
includes taxes & fees
Jul 12 - Jul 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is ￥26,369
￥59,214 total
includes taxes & fees
Aug 3 - Aug 4
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds

The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!

The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"The space was beautifully decorated, plenty of seating and space for a family getaway and the view was perfect. Our kids enjoyed the playset and the quick walk to the beach. Our host was proactive in communication and very warm and inviting. "
United States
Peter W.
The price is ￥292,626
￥417,369 total
includes taxes & fees
Jul 31 - Aug 1
The Landing at Kent Island: WATERFRONT 5BR with Pool, Firepit, Playground!
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ￥28,811
￥73,566 total
includes taxes & fees
Jul 13 - Jul 14
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
The price is ￥31,921
￥71,788 total
includes taxes & fees
Jul 27 - Jul 28
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is ￥34,948
￥44,488 total
includes taxes & fees
Jul 11 - Jul 12
Sailboat Experience in Annapolis
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (117 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
The price is ￥16,074
￥25,790 total
includes taxes & fees
Jul 13 - Jul 14
First Floor Studio Apartment in Historic Chestertown
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥20,133
￥47,851 total
includes taxes & fees
Jul 23 - Jul 24
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥28,413
￥59,031 total
includes taxes & fees
Jul 15 - Jul 16
Bayside Cottage steps from Rock Hall Harbor
Beach nearby

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is ￥20,867
￥62,814 total
includes taxes & fees
Jul 12 - Jul 13
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ￥17,119
￥48,241 total
includes taxes & fees
Jul 14 - Jul 15
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥29,225
￥45,091 total
includes taxes & fees
Aug 9 - Aug 10
BAYSIDE BUNGALOW
Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is ￥99,423
￥138,185 total
includes taxes & fees
Jul 12 - Jul 13
Wren Retweet- Country Estate in Center of C’Town
Terrace/patio

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
The price is ￥16,220
￥45,328 total
includes taxes & fees
Jul 15 - Jul 16
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

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, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is ￥30,848
￥65,151 total
includes taxes & fees
Jul 27 - Jul 28
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
The price is ￥38,642
￥100,319 total
includes taxes & fees
Jul 16 - Jul 17
Renovated Bungalow | Walk to Beach | Dog-Friendly
Fridge, microwave, oven, stovetop

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Just as advertised no issues. Great stay"
United States
Dan O.
The price is ￥14,028
￥38,017 total
includes taxes & fees
Jul 12 - Jul 13
Cute, Cozy 2-bedroom house near Annapolis with water access
Smart TV, stereo

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (17 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is ￥10,066
￥17,398 total
includes taxes & fees
Jul 21 - Jul 22
Lower Level Loft - Adorable Studio Apt. Near BWI
Fridge, microwave, oven, stovetop

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 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 ￥31,335
￥77,552 total
includes taxes & fees
Jul 12 - Jul 13
Pool Loft Suite | Bay Access & Beach Passes
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kent Island Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"Clean place, convenient, freindly staff. Noisy from The Jetty, though"
Bernard 1-night trip
Posted 13 hours ago
Hilton Garden Inn Kent Island Marina

Find out more about Kent Island

Search for holiday rentals in Kent Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Kent Island using one of the methods below:

  • View our selection of featured holiday rentals in Kent Island
  • Use the map to find apartments and other holiday homes in the Kent Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kent Island while they last

Look no further and take a look at our great range of rental properties in Kent Island!

Explore a world of travel with Expedia