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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 62 Cottages in Shelter Island Heights with updated reviews, rates, and availability.

Remodeled Farmhouse in Waterford Near 2 Beaches!
House (2 Bedrooms) | Interior

Remodeled Farmhouse in Waterford Near 2 Beaches!

3.0 star property
10.0 out of 10, Exceptional, (1)
Remodeled Farmhouse in Waterford Near 2 Beaches!
Hamptons Bay Home on Shinnecock Bay w/ Yard!
House (2 Bedrooms) | Private kitchen | Paper towels

Hamptons Bay Home on Shinnecock Bay w/ Yard!

3.0 star property
Hamptons Bay Home on Shinnecock Bay w/ Yard!
Charming Old Lyme Cottage, Steps to Private Beach!
Cottage (2 Bedrooms) | Private kitchen

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!
Property grounds

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!
Hamptons Vacation Rental w/ Seasonal Pool!
Property grounds

Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Villa Gavin
Villa (3 Bedrooms) | Living area | 45-inch flat-screen TV with cable channels, TV, fireplace

Villa Gavin

3.5 star property
Villa Gavin
Shelter Island Retreat w/ Outdoor Pool!
Outdoor pool

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Historic Essex Home w/ Large Yard Near Downtown!
TV

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!
Westbrook Home w/ Ocean Views - Walk to Beach
Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Deluxe Waterford Home w/ Views, Outdoor Bar & More
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Deluxe Waterford Home w/ Views, Outdoor Bar & More

3.0 star property
Deluxe Waterford Home w/ Views, Outdoor Bar & More
Waterfront Cottage w/ Sunroom + Patio & Grill
Living area

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Unique Southampton Getaway w/ Rooftop Deck!
Interior

Unique Southampton Getaway w/ Rooftop Deck!

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

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!
Walk to Beach: Long Island Wine Country Home!
House (3 Bedrooms) | Interior

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Charming Old Saybrook Home: Half-mi to Sand & Sea!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Mattituck Home w/ Fireplaces - Near Wineries
TV, fireplace

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Pet-friendly Home w/ Hot Tub Near the Hamptons!
Interior

Pet-friendly Home w/ Hot Tub Near the Hamptons!

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!
4 Mi to Beach: Furnished Deck at Waterford Home!
Living area

4 Mi to Beach: Furnished Deck at Waterford Home!

3.0 star property
4 Mi to Beach: Furnished Deck at Waterford Home!
Charming Hampton Bays Home 5 Mi to Coopers Beach
Terrace/patio

Charming Hampton Bays Home 5 Mi to Coopers Beach

3.0 star property
Charming Hampton Bays Home 5 Mi to Coopers Beach
Charming Westbrook Cottage, Steps to Private Beach
Interior

Charming Westbrook Cottage, Steps to Private Beach

3.0 star property
Charming Westbrook Cottage, Steps to Private Beach
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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Other property types in Shelter Island Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1162)
"Above and beyond what we expected for an off-season stay! Beautifully maintained property, gorgeous view from our room's balcony, kind and helpful staff. Will definitely be back in the near future."
The price is NT$4,918
NT$6,256 total
includes taxes & fees
May 12 - May 13
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (371)
"Perfect for a quick getaway. The location can’t be beat. Loved the beach-themed decor also."
The price is NT$4,425
NT$5,409 total
includes taxes & fees
Apr 27 - Apr 28
Montauk Oceanside Suites
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"2nd loft bedroom/bath was especially nice"
The price is NT$4,641
NT$6,010 total
includes taxes & fees
Apr 29 - Apr 30
Windward Shores Ocean Resort
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.