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Kent Island Holiday Rentals

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Holiday Rentals in Kent Island

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (14)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
United States
Tammy S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
7.0 out of 10, Good, (6)
"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

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is NZ$477
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
10.0 out of 10, Exceptional, (196)
"We had a great time with friends on our annual MD golf trip. Hal was great and the place was perfect for our group."
United States
Jason R.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
10.0 out of 10, Exceptional, (55)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
United States
Nick B.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville
9.8 out of 10, Exceptional, (44)
"Great for our purposes"
United States
Glenn F.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

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

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is NZ$1,574
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville
9.8 out of 10, Exceptional, (45)
"First time on a houseboat, very relaxing, enjoyed our stay."
United States
Frank P.
Chesapeake Houseboat Getaway on Kent Island, Maryland

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester
10.0 out of 10, Exceptional, (126)
"Family lives 1 mile from this property and we needed a little bit larger place to accommodate 5 adults for family traveling to the area for KI High School graduation. Everyone was extremely happy with the location, the house and the water front views."
United States
Stephanie S.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville
9.8 out of 10, Exceptional, (57)
"We had a wonderful time staying at your farmhouse! We found it easy to navigate to and the house is as charming as ever. We really enjoyed the private pool during the day and walking down to the deep water dock to take in the picturesque scenery in the evenings. Would absolutely stay here again."
United States
Peggs111
Circa 1700 Chesapeake Colonial home on the National Register.

25-50% Off~Private Beach~Hot Tub~Fire Table~

Stevensville
10.0 out of 10, Exceptional, (31)
"Cute little cottage with great views and very comfortable for a small family. "
United States
Susie S.
25-50% Off~Private Beach~Hot Tub~Fire Table~

40' Bristol sailboat with spectacular views

2.0 star property
Stevensville
The price is NZ$777
includes taxes & fees
22 Nov - 23 Nov
40' Bristol sailboat with spectacular views

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (31)
"The location is fabulous. We could walk wherever we wanted to go. The room to bathroom ration was also great. We would stay here again. "
United States
Diana L.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
9.8 out of 10, Exceptional, (13)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (44)
"If you’re looking for a great view sitting on the water, with a modern look, convenient to everything, you need to stay on the Cass-and-Reel Luxury Houseboat!!"
United States
Karen B.
Cass-N-Reel Luxury Houseboat

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 NZ$506
includes taxes & fees
11 Nov - 12 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena
9.4 out of 10, Exceptional, (89)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
United States
Tom S.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Waterfront Getaway, Dock Your Boat & Play!

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.
The price is NZ$547
includes taxes & fees
11 Nov - 12 Nov
Waterfront Getaway, Dock Your Boat & Play!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (17)
"The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!"
United States
Elizabeth B.
The price is NZ$2,062
includes taxes & fees
12 Nov - 13 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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

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 favorite 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 depends 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 NZ$477 per night. Entering your travel dates in the search wizard you might find 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.