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

Kent Island Vacation Rentals

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$269 nightly
The price is $289
Nov 2 - Nov 3
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 a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$260 nightly
The price is $279
Nov 1 - Nov 2
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Three birds perched on a wooden structure by the 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)
"Just what was needed for our weekend stay."
United States
barbara s.
$1,256 nightly
The price is $1,386
Nov 1 - Nov 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.
$1,256 nightly
The price is $1,386
Nov 2 - Nov 3
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
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
$994 nightly
The price is $1,054
Oct 30 - Oct 31
Total with taxes and fees
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A waterfront patio with outdoor seating and umbrellas, overlooking a river with boats and a bridge in the background.

6. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (110 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat
A deck with a view of a marina, including boats and docks.

7. 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
$254 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
A beach with chairs and a pier in the background.

8. 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.
$422 nightly
The price is $481
Nov 3 - Nov 4
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

9. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$463 nightly
The price is $521
Nov 5 - Nov 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
$466 nightly
The price is $531
Nov 1 - Nov 2
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.

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$483 nightly
The price is $551
Nov 1 - Nov 2
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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.
$444 nightly
The price is $506
Nov 4 - Nov 5
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A kitchen with a wooden countertop, a stove, and a refrigerator.

13. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
$392 nightly
The price is $447
Oct 30 - Oct 31
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

14. 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.
$683 nightly
The price is $778
Nov 2 - Nov 3
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. 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.
$522 nightly
The price is $595
Nov 9 - Nov 10
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

16. 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.
$509 nightly
The price is $580
Nov 1 - Nov 2
Total with taxes and fees
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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.

17. 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.
$440 nightly
The price is $502
Nov 3 - Nov 4
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

18. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$621 nightly
The price is $708
Oct 30 - Oct 31
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
A two-story house with a covered patio, a garage, and a well-maintained lawn.

19. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (56 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
$432 nightly
The price is $492
Oct 30 - Oct 31
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

20. 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.
$487 nightly
The price is $555
Oct 30 - Oct 31
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-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

St Michaels Inn

St Michaels Inn

8/10 Good
"Breakfasr was in lobby consisting of package roles and coffee. No toaster, no microwave, no cereal or eggs or bacon or yougert. Room and parking and staff werefine."
John 1-night trip
Posted 7 hours ago
St Michaels Inn

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 $210 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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