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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 Heights Holiday Homes

Serene Island Getaway with Tennis, Pickleball, Free Bikes & Watersports
A heated pool

Serene Island Getaway with Tennis, Pickleball, Free Bikes & Watersports

The price is £1,032
includes taxes & fees
10 Sept - 11 Sept
Serene Island Getaway with Tennis, Pickleball, Free Bikes & Watersports
Waterfront Retreat with Heated Pool, Spa & Seasonal Water Sports
A heated pool

Waterfront Retreat with Heated Pool, Spa & Seasonal Water Sports

The price is £1,085
includes taxes & fees
10 Sept - 11 Sept
Waterfront Retreat with Heated Pool, Spa & Seasonal Water Sports
Relaxing Waterfront Escape with Wellness & Outdoor Activities
A heated pool

Relaxing Waterfront Escape with Wellness & Outdoor Activities

The price is £1,385
includes taxes & fees
1 Sept - 2 Sept
Relaxing Waterfront Escape with Wellness & Outdoor Activities
Relaxing Cottages & Spacious Rooms w/ Beach Access, Pool, Spa and Free Bikes
A heated pool

Relaxing Cottages & Spacious Rooms w/ Beach Access, Pool, Spa and Free Bikes

The price is £1,214
includes taxes & fees
1 Sept - 2 Sept
Relaxing Cottages & Spacious Rooms w/ Beach Access, Pool, Spa and Free Bikes
Shelter Island Retreat with Spa Facility, Seasonal Heated Pool & Kayaking
A heated pool

Shelter Island Retreat with Spa Facility, Seasonal Heated Pool & Kayaking

The price is £1,295
includes taxes & fees
10 Sept - 11 Sept
Shelter Island Retreat with Spa Facility, Seasonal Heated Pool & Kayaking
Unwind with Stunning Ocean Views, Heated Pool and Spa Facility
A heated pool

Unwind with Stunning Ocean Views, Heated Pool and Spa Facility

The price is £768
includes taxes & fees
10 Sept - 11 Sept
Unwind with Stunning Ocean Views, Heated Pool and Spa Facility
Waterfront Escape with Scenic Views, Spa & Outdoor Adventures
A heated pool

Waterfront Escape with Scenic Views, Spa & Outdoor Adventures

The price is £697
includes taxes & fees
10 Sept - 11 Sept
Waterfront Escape with Scenic Views, Spa & Outdoor Adventures
Tranquil Hideaway with Pool, Spa, Game Room & Outdoor Fun Activities
A heated pool

Tranquil Hideaway with Pool, Spa, Game Room & Outdoor Fun Activities

The price is £1,603
includes taxes & fees
1 Sept - 2 Sept
Tranquil Hideaway with Pool, Spa, Game Room & Outdoor Fun Activities
Peaceful Island Stay with Spa, Tennis Court, Seasonal Heated Pool & Watersports
A heated pool

Peaceful Island Stay with Spa, Tennis Court, Seasonal Heated Pool & Watersports

The price is £1,757
includes taxes & fees
10 Sept - 11 Sept
Peaceful Island Stay with Spa, Tennis Court, Seasonal Heated Pool & Watersports
Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is £12,383
includes taxes & fees
18 Aug - 19 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 £5,803
includes taxes & fees
10 Sept - 11 Sept
Sag Harbor Water View w Dock 1.5ml from town
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
Terrace/patio

Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is £4,426
includes taxes & fees
3 Sept - 4 Sept
Luxury 7BR Hamptons Estate – Prime Central Location, Mins to Beach & Horse Show
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 £345
includes taxes & fees
10 Sept - 11 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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 £4,854
includes taxes & fees
23 Aug - 24 Aug
Spacious 5-bedroom house with water views and 2 houses from the bay.
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
18 Aug - 19 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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 £416
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 £370
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 £376
includes taxes & fees
16 Sept - 17 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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 £424
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 £3,356
includes taxes & fees
16 Sept - 17 Sept
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
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 Heights Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"The staff was knowledgeable and courteous. The cleaning crew cleaned the room exceptionally well. The view of the ocean from the room was breathtaking. I will definitely go back. "
Kimberly 2-night trip
Posted 10 hours ago
Beachcomber Resort at Montauk