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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Shelter Island

Hamptons Vacation Rental w/ Seasonal Pool!
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Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Dreamy Waterfront Westbrook Home on Private Beach
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Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
Charming Old Lyme Cottage, Steps to Private Beach!
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Charming Old Lyme Cottage, Steps to Private Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming Old Lyme Cottage, Steps to Private Beach!
Cozy Westbrook Vacation Rental - Walk to Beach!
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Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Private kitchen

Deluxe Waterford Home w/ Views, Outdoor Bar & More

3.0 star property
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Westbrook Home w/ Ocean Views - Walk to Beach
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Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Hamptons Bay Home on Shinnecock Bay w/ Yard!
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Hamptons Bay Home on Shinnecock Bay w/ Yard!

3.0 star property
Hamptons Bay Home on Shinnecock Bay w/ Yard!
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
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Classy Getaway w/ Deck & Yard < 1 Mi to Beach

3.0 star property
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
Walk to Beach: Long Island Wine Country Home!
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Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Charming Hampton Bays Home 5 Mi to Coopers Beach
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Charming Hampton Bays Home 5 Mi to Coopers Beach

3.0 star property
Charming Hampton Bays Home 5 Mi to Coopers Beach
Pet-friendly Home w/ Hot Tub Near the Hamptons!
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Pet-friendly Home w/ Hot Tub Near the Hamptons!

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!
Unique Southampton Getaway w/ Rooftop Deck!
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Unique Southampton Getaway w/ Rooftop Deck!

3.0 star property
Unique Southampton Getaway w/ Rooftop Deck!
Hampton Bays Retreat: Walk to Squires Beach!
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Hampton Bays Retreat: Walk to Squires Beach!

3.0 star property
6.0 out of 10, (1)
"Getting in and out of the property was very difficult. All the codes for the front door did not work and we were on the phone for an hour trying to get in. We had to go through the rental company as the owner didn’t answer any of our calls or texts. Also, locking the front door was very problematic. None of the shampoo, conditioner, or soap dispensers worked. The sheets were so itchy and horrible that we had to switch from the queen bed to the twin beds. Overall, the beds didn’t feel very clean...
Hampton Bays Retreat: Walk to Squires Beach!
Waterfront Cottage w/ Sunroom + Patio & Grill
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Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Historic Essex Home w/ Large Yard Near Downtown!
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Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing Host. Fantastic trip "
Historic Essex Home w/ Large Yard Near Downtown!
Shelter Island Retreat w/ Outdoor Pool!
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Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Mattituck Home w/ Fireplaces - Near Wineries
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Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Cute East Hampton Cottage w/ Patio - Walk to Beach
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Cute East Hampton Cottage w/ Patio - Walk to Beach

3.0 star property
Cute East Hampton Cottage w/ Patio - Walk to Beach
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Private kitchen

Charming Old Saybrook Home: Half-mi to Sand & Sea!

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Walk to Amagansett Beach: Cottage w/ Deck!
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Walk to Amagansett Beach: Cottage w/ Deck!

3.0 star property
Walk to Amagansett Beach: Cottage w/ Deck!
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"we just needed a simple inexpensive room for the night and this place was perfect. No fuss."
Al 1-night trip
Posted 10 hours ago
Pier Blue Inn Old Saybrook - Essex

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