Holiday Homes in Kent Island

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Check prices for these dates

Our top choices for Kent Island holiday homes

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.
The price is NZ$581
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!

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.
The price is NZ$509
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview

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.
The price is NZ$2,211
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

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.
The price is NZ$2,211
includes taxes & fees
1 Dec - 2 Dec
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

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 traveller
The price is NZ$1,763
includes taxes & fees
15 Nov - 16 Nov
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

6. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is NZ$545
includes taxes & fees
24 Nov - 25 Nov
Family Friendly Cozy 3 Bedroom Duplex

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.
The price is NZ$837
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

8. 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 NZ$958
includes taxes & fees
30 Nov - 1 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!

9. 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.
The price is NZ$950
includes taxes & fees
15 Nov - 16 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly

10. 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, (44 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 NZ$541
includes taxes & fees
22 Nov - 23 Nov
Large 2 bedroom house with private parking in a nice neighborhood

11. 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.
The price is NZ$1,089
includes taxes & fees
15 Nov - 16 Nov
5 bedroom house with EV charger Near Downtown Annapolis

12. 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 NZ$1,175
includes taxes & fees
14 Nov - 15 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10

13. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is NZ$783
includes taxes & fees
1 Dec - 2 Dec
Sunset Cottage - West River Access and Views!

14. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is NZ$355
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access

15. 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.
The price is NZ$1,090
includes taxes & fees
17 Nov - 18 Nov
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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.
The price is NZ$1,041
includes taxes & fees
17 Nov - 18 Nov
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

17. 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.
The price is NZ$744
includes taxes & fees
30 Nov - 1 Dec
Cozy 2br home w/ parking in downtown Annapolis

18. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The property was beautiful, exceptionally clean, and in a perfect location for enjoying everything Annapolis has to offer. The beds were very comfortable, and the home had wonderful amenities that made our stay even more enjoyable. We couldn’t have asked for a better place to stay and would absolutely return. Highly recommend!"
United States
Dayna A.
The price is NZ$751
includes taxes & fees
15 Nov - 16 Nov
The Harness Creek Retreat in Annapolis

19. 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.
The price is NZ$1,039
includes taxes & fees
30 Nov - 1 Dec
Cute bungalow blocks to Stadium

20. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (18 reviews)
"Very nice home. Definitely recommend!"
United States
Bob H.
The price is NZ$722
includes taxes & fees
17 Nov - 18 Nov
Fabulous 5-bedroom house with AC in charming Annapolis
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.

Learn more about Kent Island

Cross the Chesapeake Bay Bridge to discover Kent Island's scenic waterfront and fresh seafood restaurants. Kayak through tranquil creeks, cycle the Cross Island Trail, or visit historic Stevensville for a taste of Eastern Shore charm.

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

Top reviews in Kent Island

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