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Holiday Homes in Shelter Island
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Featured Holiday Homes in Shelter Island
The Hampton Sack a cheerful relaxing beach cottage
The Hampton Sack a cheerful relaxing beach cottage
7.6 out of 10, Good, 13 reviews
North Fork Escape Near Wineries, Beaches And Hamptons
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
9.0 out of 10, Wonderful, 2 reviews
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Patchogue River Retreat, 8 minute walk to West Beach
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, 1 review
The price is NZ$2,897
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, 7 reviews
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
10.0 out of 10, Exceptional, 30 reviews
Gorgeous Garden Home with secluded and heated pool, quiet getaway
Gorgeous Garden Home with secluded and heated pool, quiet getaway
10.0 out of 10, Exceptional, 7 reviews
Lovely Westbrook Home w/ Patio - Walk to Beach!
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, 1 review
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 74 reviews
Get out of the heat! Amazing home with pool, hot tub, pirate ship and much more!
Get out of the heat! Amazing home with pool, hot tub, pirate ship and much more!
10.0 out of 10, Exceptional, 70 reviews
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, 9 reviews
Sun Drenched East Hampton Springs Retreat with Private Beach Pass
Sun Drenched East Hampton Springs Retreat with Private Beach Pass
Cozy Ocean front view, Beach house , lay in bed and hear the waves! Waterford CT
Cozy Ocean front view, Beach house , lay in bed and hear the waves! Waterford CT
10.0 out of 10, Exceptional, 6 reviews
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
9.0 out of 10, Wonderful, 9 reviews
Niantic Cottage Minutes from Beach | Play & Relax
Niantic Cottage Minutes from Beach | Play & Relax
10.0 out of 10, Exceptional, 5 reviews
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, 4 reviews
The price is NZ$11,532
includes taxes & fees
2 July - 3 July
2 Jul - 3 Jul
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, 86 reviews
The price is NZ$1,493
includes taxes & fees
26 June - 27 June
26 Jun - 27 Jun
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.
Other property types in Shelter Island
Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, 1,030 reviews
The price is NZ$766
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, 240 reviews
The price is NZ$668
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
The Surf Club
The Surf Club
8.6 out of 10, Excellent, 224 reviews
The price is NZ$620
includes taxes & fees
24 June - 25 June
24 Jun - 25 Jun
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.
Shelter Island Holiday Homes information
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Recent Reviews in Shelter IslandExpedia verified reviews
5/5 Excellent
"The pool closed too early. "
A verified traveller from Green Bay stayed at Sag Harbor Inn
Posted 23 hours ago
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