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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Shelter Island Holiday Homes

Huge Island Getaway Pool Hot Tub Walk To Beach
Beach nearby

Huge Island Getaway Pool Hot Tub Walk To Beach

10.0 out of 10, Exceptional, (7)
"Property great. Beautiful home with great amenities"
The price is £2,077
includes taxes & fees
31 Aug - 1 Sept
Huge Island Getaway Pool Hot Tub Walk To Beach
Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (49)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
The price is £1,085
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is £394
includes taxes & fees
17 Aug - 18 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Fridge, microwave, oven, stovetop

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

10.0 out of 10, Exceptional, (9)
"Open concept home beautiful with private yard space. It was perfect for our stay"
The price is £350
includes taxes & fees
2 Sept - 3 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Rogers Lake House (87) · CT College+Beach+USCGA
Property grounds

Rogers Lake House (87) · CT College+Beach+USCGA

10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
The price is £417
includes taxes & fees
10 Sept - 11 Sept
Rogers Lake House (87) · CT College+Beach+USCGA
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!"
The price is £362
includes taxes & fees
15 Sept - 16 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Beach nearby, sun-loungers, beach towels

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "
The price is £398
includes taxes & fees
3 Sept - 4 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is £12,453
includes taxes & fees
16 Aug - 17 Aug
Stunning Southampton Village Modern Home
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is £5,815
includes taxes & fees
10 Sept - 11 Sept
Sag Harbor Water View w Dock 1.5ml from town
Shoreline Oasis
Exterior

Shoreline Oasis

9.0 out of 10, Wonderful, (6)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is £194
includes taxes & fees
26 Aug - 27 Aug
Shoreline Oasis
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is £4,795
includes taxes & fees
20 Aug - 21 Aug
Spacious 5-bedroom house with water views and 2 houses from the bay.
adorable ranch in beach community
Beach nearby

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is £362
includes taxes & fees
15 Sept - 16 Sept
adorable ranch in beach community
Cozy quiet gem, private & fenced in backyard
Fridge, microwave, oven, stovetop

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is £1,182
includes taxes & fees
18 Aug - 19 Aug
Cozy quiet gem, private & fenced in backyard
Aqua by American Beech - Rooftop Suite
Terrace/patio

Aqua by American Beech - Rooftop Suite

10.0 out of 10, Exceptional, (1)
"Quick stay after a day at the wineries. Location is is set in a beautiful quiet area and the view is just amazing. The staff could truly not be any better, any request or issue was dealt with in literally a minute. Room was perfect, clean and made you feel at home with anything you needed. Will definitely be back!"
The price is £425
includes taxes & fees
9 Sept - 10 Sept
Aqua by American Beech - Rooftop Suite
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
The price is £3,486
includes taxes & fees
15 Sept - 16 Sept
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
Exterior detail

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

9.8 out of 10, Exceptional, (19)
"House was perfectly appointed in Southampton! Close to all the spots--Southampton town, Bridgehampton shopping and quaint Sag Harbor"
The price is £2,366
includes taxes & fees
24 Aug - 25 Aug
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is £270
includes taxes & fees
20 Aug - 21 Aug
American Beech in Greenport - Petite King Room 7
Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is £887
includes taxes & fees
18 Aug - 19 Aug
Beautifully farmhouse
Aqua by American Beech - Superior King
Property grounds

Aqua by American Beech - Superior King

10.0 out of 10, Exceptional, (5)
"Very clean, flexible, great communication and exceptional view"
The price is £324
includes taxes & fees
1 Sept - 2 Sept
Aqua by American Beech - Superior King
Bay Access Cottage + Pilates Gym
Beach nearby, sun-loungers, beach towels

Bay Access Cottage + Pilates Gym

2.0 star property
The price is £533
includes taxes & fees
9 Sept - 10 Sept
Bay Access Cottage + Pilates Gym
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

Greenporter Hotel

Greenporter Hotel

10/10 Excellent
"Great location, clean, staff very nice"
Karen 2-night trip
Posted 8 hours ago
Greenporter Hotel