A wooden gazebo by a pond with a large tree trunk nearby.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Shelter Island cottages

Balcony

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AU$504
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
Terrace/patio

2. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is AU$1,516
includes taxes & fees
9 Sept - 10 Sept
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AU$312
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

4. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is AU$852
includes taxes & fees
8 Sept - 9 Sept
Seabreeze #3 Cozy Cottage steps to the beach
Exterior

5. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is AU$504
includes taxes & fees
24 Aug - 25 Aug
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

6. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (32 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is AU$687
includes taxes & fees
25 Aug - 26 Aug
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Exterior

7. Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
The price is AU$1,236
includes taxes & fees
23 Aug - 24 Aug
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Exterior

8. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AU$852
includes taxes & fees
8 Sept - 9 Sept
Seabreeze 4 Charming Cottage footsteps to beach
Exterior

9. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is AU$1,270
includes taxes & fees
24 Aug - 25 Aug
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

10. Large Family-Friendly Cottage

Large Family-Friendly Cottage
Waterford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our weekend at Marina Bay for our daughter’s birthday weekend with her friends. Everything was easy to find and use, the space was perfectly sized and comfortable. We hope to return soon!"
United States
Henry B.
The price is AU$576
includes taxes & fees
30 Aug - 31 Aug
Large Family-Friendly Cottage
Exterior

11. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
The price is AU$997
includes taxes & fees
14 Sept - 15 Sept
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Exterior

12. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
The price is AU$1,248
includes taxes & fees
23 Aug - 24 Aug
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Terrace/patio

13. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
The price is AU$1,248
includes taxes & fees
26 Aug - 27 Aug
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Smart TV, table football, ping pong

14. Sun-Filled Private Large Cottage

Sun-Filled Private Large Cottage
Waterford
Sun-Filled Private Large Cottage
Exterior detail

15. Private Two-Bedroom Cottage

Private Two-Bedroom Cottage
Waterford
6.0 out of 10, (1 review)
The price is AU$669
includes taxes & fees
19 Sept - 20 Sept
Private Two-Bedroom Cottage
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 Shelter Island Hotel Reviews

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"The room was beautifully decorated, clean and spacious. The staff were friendly and helpful. The grounds were beautifully maintained. We enjoyed our stay. Perfect location on the water with nice restaurants nearby."
Jeanne 1-night trip
Posted 11 hours ago
The Shoals Suites and Slips

Find out more about Shelter Island

Shelter Island Cottages information

Number of reviews
169
Accommodation
226 Cottages
Lowest Price
AU$312
Highest Price
AU$1,516