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

Kent Island Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Kent Island vacation rentals

A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
$257 nightly
The price is $276
Nov 11 - Nov 12
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$282 nightly
The price is $304
Nov 15 - Nov 16
Total with taxes and fees
Relax on Kent Island in 4 Bedroom Home w/Waterview
A boat's deck with a view of a large bridge spanning across a body of water.

3. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
$1,122 nightly
The price is $1,239
Dec 1 - Dec 2
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

4. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
$1,141 nightly
The price is $1,259
Dec 1 - Dec 2
Total with taxes and fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A two-story house with a red roof, a brick chimney, and a small porch.

5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.6 out of 10, Excellent, (7 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveler
$945 nightly
The price is $1,002
Nov 12 - Nov 13
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A deck with a view of a marina, including boats and docks.

6. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
$232 nightly
The price is $257
Nov 12 - Nov 13
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
A beach with chairs and a pier in the background.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
$414 nightly
The price is $472
Nov 16 - Nov 17
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A wooden dock extending into a calm body of water with boats docked at the end.

8. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
$378 nightly
The price is $431
Nov 11 - Nov 12
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

9. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$462 nightly
The price is $527
Nov 11 - Nov 12
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

10. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
$624 nightly
The price is $711
Nov 11 - Nov 12
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
A kitchen with a wooden countertop, a stove, and a refrigerator.

11. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
$353 nightly
The price is $403
Nov 11 - Nov 12
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Stylish kitchen with open layout and island seating

12. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$404 nightly
The price is $460
Nov 11 - Nov 12
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

13. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
$603 nightly
The price is $659
Nov 11 - Nov 12
Total with taxes and fees
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
A backyard patio with a round table and chairs, surrounded by a gravel area.

14. 5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
$531 nightly
The price is $605
Nov 15 - Nov 16
Total with taxes and fees
5 bedroom house with EV charger Near Downtown Annapolis
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

15. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
$559 nightly
The price is $637
Nov 15 - Nov 16
Total with taxes and fees
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

16. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$466 nightly
The price is $531
Nov 30 - Dec 1
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

17. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
$465 nightly
The price is $530
Nov 11 - Nov 12
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with a central island, built-in oven, and microwave.

18. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
$510 nightly
The price is $576
Nov 30 - Dec 1
Total with taxes and fees
Cute bungalow blocks to Stadium
A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

19. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
$479 nightly
The price is $546
Nov 11 - Nov 12
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Exterior detail

20. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
$439 nightly
The price is $500
Nov 11 - Nov 12
Total with taxes and fees
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"The hot tub was broken. But the staff was helpful, the rooms were big and clean"
Brian 1-night trip
Posted 14 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Kent Island

Everything you need to know about Kent Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kent Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kent Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $198 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kent Island rentals

At Expedia, we put the best Kent Island vacation 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 vacation.

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.

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