Photo by Jennifer Crim

Kent Island Holiday Rentals

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Holiday Rentals in Kent Island

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AU$821
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!

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 AU$402
includes taxes & fees
1 Dec - 2 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AU$1,366
includes taxes & fees
3 Dec - 4 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 AU$392
includes taxes & fees
1 Dec - 2 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
The price is AU$655
includes taxes & fees
1 Dec - 2 Dec
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

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

Arnold
10.0 out of 10, Exceptional, (5)
"Enjoyed the stay"
United States
Kedra B.
The price is AU$565
includes taxes & fees
2 Dec - 3 Dec
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Edgewater
The price is AU$4,770
includes taxes & fees
1 Dec - 2 Dec
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Upscale Condo in Annapolis

Historic District
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is AU$938
includes taxes & fees
8 Dec - 9 Dec
Upscale Condo in Annapolis

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 AU$687
includes taxes & fees
8 Dec - 9 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Just what we were looking for. Appreciated the little touches such as already baited crab traps and the complimentary smores kit. "
United States
Dan K.
The price is AU$581
includes taxes & fees
2 Dec - 3 Dec
Beautiful Waterfront Retreat in Cambridge!

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 AU$646
includes taxes & fees
1 Dec - 2 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$246
includes taxes & fees
1 Dec - 2 Dec
First Floor Studio Apartment in Historic Chestertown

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AU$419
includes taxes & fees
1 Dec - 2 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"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."
United States
Kristina
The price is AU$851
includes taxes & fees
2 Dec - 3 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (2)
"So comfortable for the 2 of us. Close to restaurants, shopping, liquor store and to family in Chesapeake Beach. The 2nd BR let us spread out suitcases and extras. Stocked kitchen and bath. Grill right out the door to the fenced back yard. Driveway to the door. All we needed and felt at home. "
United States
Patricia M.
The price is AU$427
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"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 AU$506
includes taxes & fees
1 Dec - 2 Dec
Walk to Beach! King Bed & Free Beach Passes

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 AU$775
includes taxes & fees
3 Dec - 4 Dec
Neptune by the Water - Pet Friendly Fenced Yard

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$705
includes taxes & fees
3 Dec - 4 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Rock Hall
10.0 out of 10, Exceptional, (17)
"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! "
United States
Tracy S.
The price is AU$453
includes taxes & fees
3 Dec - 4 Dec
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 AU$627
includes taxes & fees
1 Dec - 2 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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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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$194 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.