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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)
The price is NZ$581
includes taxes & fees
23 Nov - 24 Nov

2. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
The price is NZ$509
includes taxes & fees
15 Nov - 16 Nov

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)
The price is NZ$2,211
includes taxes & fees
1 Dec - 2 Dec

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)
The price is NZ$2,211
includes taxes & fees
1 Dec - 2 Dec

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 parkingStevensville
8.6 out of 10, Excellent, (7 reviews)
The price is NZ$1,763
includes taxes & fees
15 Nov - 16 Nov

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

7. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
The price is NZ$837
includes taxes & fees
16 Nov - 17 Nov

8. Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$958
includes taxes & fees
30 Nov - 1 Dec

9. Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
9.6 out of 10, Exceptional, (14 reviews)
The price is NZ$950
includes taxes & fees
15 Nov - 16 Nov

10. Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (44 reviews)
The price is NZ$541
includes taxes & fees
22 Nov - 23 Nov

11. 5 bedroom house with EV charger Near Downtown Annapolis
5 bedroom house with EV charger Near Downtown AnnapolisEastport
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$1,089
includes taxes & fees
15 Nov - 16 Nov

12. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$1,175
includes taxes & fees
14 Nov - 15 Nov

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)
The price is NZ$783
includes taxes & fees
1 Dec - 2 Dec

14. Cute, Cozy 2-bedroom house near Annapolis with water access
Cute, Cozy 2-bedroom house near Annapolis with water accessHerald Harbor
9.8 out of 10, Exceptional, (31 reviews)
The price is NZ$355
includes taxes & fees
15 Nov - 16 Nov

15. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and DowntownHomewood
9.8 out of 10, Exceptional, (10 reviews)
The price is NZ$1,090
includes taxes & fees
17 Nov - 18 Nov

16. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 MinCape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
The price is NZ$1,041
includes taxes & fees
17 Nov - 18 Nov

17. Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown AnnapolisHistoric District
10.0 out of 10, Exceptional, (87 reviews)
The price is NZ$744
includes taxes & fees
30 Nov - 1 Dec

18. The Harness Creek Retreat in Annapolis
The Harness Creek Retreat in AnnapolisHillsmere
10.0 out of 10, Exceptional, (1 review)
The price is NZ$751
includes taxes & fees
15 Nov - 16 Nov

19. Cute bungalow blocks to Stadium
Cute bungalow blocks to StadiumAdmiral Heights
9.4 out of 10, Exceptional, (13 reviews)
The price is NZ$1,039
includes taxes & fees
30 Nov - 1 Dec

20. Fabulous 5-bedroom house with AC in charming Annapolis
Fabulous 5-bedroom house with AC in charming AnnapolisAnnapolis
8.6 out of 10, Excellent, (18 reviews)
The price is NZ$722
includes taxes & fees
17 Nov - 18 Nov
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.

Top reviews in Kent Island

Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
















































































