Title: Shelter Island Holiday Homes from £149: Search Holiday Homes in Shelter Island | Expedia.co.uk

[Shelter Island Travel Guide](https://expedia.co.uk/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.co.uk/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Holiday Rentals in Shelter Island](https://expedia.co.uk/Shelter-Island-Holiday-Rentals.d157359.Travel-Guide-HolidayRentals)[Flights to Shelter Island](https://expedia.co.uk/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Shelter Island Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Shelter-Island.d157359.Car-Hire-Guide)[Shelter Island Holidays](https://expedia.co.uk/Shelter-Island.d157359.Holidays-City-Breaks)

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## Check prices for these dates

In two weeks

[27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[8 May - 10 May](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Shelter Island holiday homes

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/84a27bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4422918e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/997596e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Swan: Beachfront Home w/ Year-Round Jacuzzi

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

Hampton Bays

9.6/10

Exceptional

(15 reviews)

"Nice house. Photos and descriptions represent it very accurately. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Will K.

£907

includes taxes & fees

24 Feb - 25 Feb

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/40ddf6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/1d0cab84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/fde884e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123140000/123130700/123130625/a1c526db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amagansett Farmhouse Retreat - Outdoor Fireplace & Basement Arcade, Great for Kids

[](https://www.expedia.co.uk/East-Hampton-Hotels-Amagansett-Farmhouse-Retreat.h123130625.Hotel-Information)

East Hampton North

£455

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/East-Hampton-Hotels-Amagansett-Farmhouse-Retreat.h123130625.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/76a0ec07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/4f11d273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/w1330h900x18y0-56561db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/w993h1280x143y0-78873ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

[](https://www.expedia.co.uk/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information)

East Hampton North

£474

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information)

![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/9626c6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/91eb12d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/3e9c1103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/830deaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Estate for 8, Sauna, Soaking Tub, Chef\`s Kitchen, Outdoor Fireplace

[](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information)

East Hampton North

£447

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/33a85d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/b32ce68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/fda79bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4ad42a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

Waterford

10/10

Exceptional

(11 reviews)

"We had a nice stay. Kitchen well stocked and house was clean and comfortable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elaine A.

£340

includes taxes & fees

3 Mar - 4 Mar

[](https://www.expedia.co.uk/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/6f35c24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Modern Stay Steps from the Ocean

[](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

Clinton

10/10

Exceptional

(1 review)

"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly Z.

£247

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/eea5c652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/95b993b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a31fd902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/e689a456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

[](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

Clinton

10/10

Exceptional

(3 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elya D.

£364

includes taxes & fees

24 Feb - 25 Feb

[](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/f7c4e75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/7d654429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/ceb7120d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/252d3a5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

Hampon Bays

9.6/10

Exceptional

(23 reviews)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annie B.

£972

includes taxes & fees

18 Feb - 19 Feb

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Bliss w/ Game Room, Gym & Golf Green

[](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

Westbrook

10/10

Exceptional

(1 review)

"Perfect house for 6 guests. Loved that it was close to the beach."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon G.

£389

includes taxes & fees

17 Feb - 18 Feb

[](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/52990ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/146ca0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blackberry: Private home with jacuzzi year-round

[](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

East Hampton

9.0/10

Wonderful

(4 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Suzanne R.

£713

includes taxes & fees

24 Feb - 25 Feb

[](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### American Beech in Greenport - Petite King Room 7

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

Greenport

9.0/10

Wonderful

(4 reviews)

"We thoroughly enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Parent From The Heart, Inc. E.

£149

includes taxes & fees

17 Feb - 18 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/259b8f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/9ddc24ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0298db95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

Old Lyme

10/10

Exceptional

(5 reviews)

"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!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hemie J.

£495

includes taxes & fees

17 Feb - 18 Feb

[](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/103000000/102190000/102189500/102189499/3fbe5245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102190000/102189500/102189499/66e641ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/103000000/102190000/102189500/102189499/58a20b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102190000/102189500/102189499/3d345122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Great-Hammcock-Getaway.h102189499.Hotel-Information)

Old Saybrook

9.8/10

Exceptional

(9 reviews)

"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Doug F.

£369

includes taxes & fees

15 Feb - 16 Feb

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Great-Hammcock-Getaway.h102189499.Hotel-Information)

![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/c520cfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/f04ef5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/41d30343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

[](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

Water Mill

10/10

Exceptional

(6 reviews)

"Highly recommend everything from start to finish went smoothly and it was a great experience!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie M.

£4,289

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h946x0y0-a3c0ca5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w4320h3228x0y4-a36bb89d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h956x0y0-f00664d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/c23d45d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

Saybrook Manor

9.8/10

Exceptional

(136 reviews)

"We loved our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deana L.

£392

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/c1360527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/b56aaa31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/5b429221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106350000/106340600/106340524/f42f3c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach cottage, private road, private beach, private mooring, private parking. 

[](https://www.expedia.co.uk/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information)

Laurel

10/10

Exceptional

(1 review)

£576

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Laurel-Hotels-Beach-Cottage.h106340524.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-297b69ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-6196bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w906h683x58y0-bc7fef2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, Internet](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w904h683x60y0-a596b0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 5 Bedroom With Wi-fi And Air Condition

[](https://www.expedia.co.uk/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information)

Wainscott

£1,420

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/676d68a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/fdd8564b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/30220c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Northfork Townhouse walk to all

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

Greenport

10/10

Exceptional

(5 reviews)

"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Beth R.

£413

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/9304004e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/305503f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/e51e1447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/4ee29ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Immaculate Waterfront 2 bedroom! 

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information)

Hampton Bays

10/10

Exceptional

(5 reviews)

"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael L.

£471

includes taxes & fees

15 Feb - 16 Feb

[](https://www.expedia.co.uk/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/165550bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated Townhouse walk to all

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

Greenport

9.6/10

Exceptional

(10 reviews)

"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura B.

£451

includes taxes & fees

16 Feb - 17 Feb

[](https://www.expedia.co.uk/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

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.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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## Find holiday rentals that suit your style

Private holiday homes

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Aparthotels

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Cottages

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Apartments

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Condos

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Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA)

Houseboats

[](https://www.expedia.co.uk/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg)

### Montauk Manor

10/10 Excellent

"Beautiful room and beautiful setting. Love the fireplace!"

[](https://expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "

[](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![The Preston House & Hotel](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec_y.jpg)

### The Preston House & Hotel

10/10 Excellent

"Staff was amazing during the snow storm when everything in the town was closed. Also the hotel restaurant was closed so the GM prepared a salad, pasta with chick and stated veg for my husband and me. "

[](https://expedia.co.uk/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information)

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Very comfortable and enjoyable place to stay."

[](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Room was spotless, staff were great and the resort is top notch!!"

[](https://expedia.co.uk/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg)

### Offshore Montauk

10/10 Excellent

"was great."

[](https://expedia.co.uk/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "

[](https://expedia.co.uk/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Adorable room"

[](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg)

### Hyatt Place Long Island East End

10/10 Excellent

"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."

[](https://expedia.co.uk/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

## Find out more about Shelter Island

## Shelter Island Holiday Homes information

| Number of reviews | 178                |
| ----------------- | ------------------ |
| Accommodation     | 1792 Holiday Homes |
| Lowest Price      | £149               |
| Highest Price     | £4,289             |

## Explore a world of travel with Expedia

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