Photo by Jennifer Crim

Kent Island Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Kent Island

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is AU$406
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$426
includes taxes & fees
21 Oct - 22 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is AU$1,414
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
40' Bristol sailboat with spectacular views
2.0 star property
The price is AU$666
includes taxes & fees
19 Oct - 20 Oct
40' Bristol sailboat with spectacular views
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
The price is AU$615
includes taxes & fees
20 Oct - 21 Oct
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is AU$711
includes taxes & fees
27 Oct - 28 Oct
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
The price is AU$4,791
includes taxes & fees
18 Oct - 19 Oct
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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. "
The price is AU$637
includes taxes & fees
17 Oct - 18 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
The price is AU$423
includes taxes & fees
18 Oct - 19 Oct
Chesapeake Bay Harbor View in a central location to events/restaurants
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (47)
"Property was as listed. We enjoyed are stay."
The price is AU$610
includes taxes & fees
21 Oct - 22 Oct
Beautiful Waterfront Retreat in Cambridge!
HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (6)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
The price is AU$691
includes taxes & fees
27 Oct - 28 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
The price is AU$431
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$818
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (2)
"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!"
The price is AU$560
includes taxes & fees
22 Oct - 23 Oct
Bayside Cottage steps from Rock Hall Harbor
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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 "
The price is AU$887
includes taxes & fees
20 Oct - 21 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
The price is AU$454
includes taxes & fees
21 Oct - 22 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$247
includes taxes & fees
20 Oct - 21 Oct
First Floor Studio Apartment in Historic Chestertown
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
The price is AU$867
includes taxes & fees
19 Oct - 20 Oct
Charming Pet-Friendly Stay - Near Bay & Beaches.
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
The price is AU$469
includes taxes & fees
19 Oct - 20 Oct
BAYSIDE BUNGALOW
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
The price is AU$713
includes taxes & fees
19 Oct - 20 Oct
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kent Island Hotel Reviews

Find out more about Kent Island

Everything you need to know about Kent Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kent Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Kent Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kent Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kent Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent Island holiday rentals we have selected for you start as low as AU$406 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Kent Island rentals

At Expedia, we put the best Kent Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kent Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kent Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kent Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.