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

Kent Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥12,606
￥43,863 total
includes taxes & fees
Oct 14 - Oct 15
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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥18,617
￥49,361 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is ￥126,162
￥218,898 total
includes taxes & fees
Oct 21 - Oct 22
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, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is ￥110,817
￥199,553 total
includes taxes & fees
Oct 11 - Oct 12
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
8.0 out of 10, Very good, (5 reviews)
"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...
United States
Suzanne R.
The price is ￥113,688
￥166,370 total
includes taxes & fees
Oct 16 - Oct 17
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A beach with chairs and a pier in the background.

6. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is ￥33,245
￥76,340 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

7. 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.
The price is ￥45,476
￥68,421 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

8. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is ￥79,155
￥126,873 total
includes taxes & fees
Nov 8 - Nov 9
Secluded Cozy Cottage in Historic Downtown
A wooden dock extending into a calm body of water with boats docked at the end.

9. 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.
The price is ￥39,578
￥76,341 total
includes taxes & fees
Oct 20 - Oct 21
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.

10. 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
The price is ￥26,946
￥76,378 total
includes taxes & fees
Nov 1 - Nov 2
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Stylish kitchen with open layout and island seating

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥33,055
￥80,094 total
includes taxes & fees
Oct 13 - Oct 14
Pool Loft Suite | Bay Access & Beach Passes
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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.
The price is ￥35,936
￥96,192 total
includes taxes & fees
Nov 3 - Nov 4
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

13. 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.
The price is ￥35,145
￥94,568 total
includes taxes & fees
Nov 9 - Nov 10
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.

14. 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
9.0 out of 10, Wonderful, (18 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is ￥55,567
￥104,314 total
includes taxes & fees
Oct 12 - Oct 13
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

15. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (42 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is ￥22,084
￥53,330 total
includes taxes & fees
Oct 12 - Oct 13
Large 2 bedroom house with private parking in a nice neighborhood
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

16. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (12 reviews)
"The home was well stocked with all the items needed to cook and spotless. Very comfortable and easy walk to the Navy stadium. Enjoyed our stay and all that Annapolis has to share. "
United States
Veronica D.
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
A two-story house with a covered patio, a garage, and a well-maintained lawn.

17. 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, (55 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is ￥60,554
￥78,958 total
includes taxes & fees
Oct 19 - Oct 20
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,580
￥46,369 total
includes taxes & fees
Oct 12 - Oct 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

19. 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.
The price is ￥41,952
￥116,766 total
includes taxes & fees
Oct 22 - Oct 23
Family Home on Mayo Peninsula | Deck | Sleeps 10
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

20. Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (21 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
The price is ￥45,910
￥75,258 total
includes taxes & fees
Nov 9 - Nov 10
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"We stayed overnight after a wedding. Beautiful hotel so convenient with the provided shuttles. We have another wedding next year and will definitely be staying again!"
Jennifer 1-night trip
Posted less than an hour ago
The Inn at Chesapeake Bay Beach Club

Find out more about Kent Island

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