Photo by tom owens
Search Holiday Rentals in Shelter Island
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Top Holiday Rentals in Shelter Island

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1239)
The price is 7.814.961 ₫
9.443.736 ₫ total
includes taxes & fees
2 Sept - 3 Sept

Montauk Oceanside Suites
Montauk Oceanside Suites
8.6 out of 10, Excellent, (405)
The price is 5.221.815 ₫
6.251.969 ₫ total
includes taxes & fees
3 Sept - 4 Sept

The Surf Club
The Surf Club
8.6 out of 10, Excellent, (273)
The price is 8.871.086 ₫
11.569.572 ₫ total
includes taxes & fees
10 Sept - 11 Sept

Cliffside Resort Condominiums
Cliffside Resort Condominiums
9.0 out of 10, Wonderful, (238)
The price is 8.746.342 ₫
11.138.637 ₫ total
includes taxes & fees
11 Sept - 12 Sept

Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (291)
The price is 4.404.555 ₫
5.606.372 ₫ total
includes taxes & fees
14 Sept - 15 Sept

Driftwood Resort
Driftwood Resort
9.0 out of 10, Wonderful, (229)
The price is 5.384.955 ₫
7.009.783 ₫ total
includes taxes & fees
3 Sept - 4 Sept

Offshore Residences
Offshore Residences
The price is 23.875.101 ₫
30.283.563 ₫ total
includes taxes & fees
1 Sept - 2 Sept

Canoe Place Waterfront Residences
Canoe Place Waterfront Residences
10.0 out of 10, Exceptional, (1)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex
10/10 Excellent