Title: Holiday Rentals Shelter Island from £135: Find Short-Term Rentals & Holiday Accommodations | 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)[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) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Shelter Island - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Shelter Island ![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/312e44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/a1d1bd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Shelter Island 10/10 Exceptional (52) "Really great property, had a relaxing lovely time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nava S. £1,034 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/85d04a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/e4120ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/c66a667e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/bebec502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Houseboat in Old Lyme £292 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen | Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Montauk 9.2/10 Wonderful (1262) "Always excellent, even suring my eleventh stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl £135 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/6b9fb589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/58473cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Greenport 9.4/10 Exceptional (6) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin £169 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/10f54062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Hampton Bays 10/10 Exceptional (1) £345 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/ec09d195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/f3aa91d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/41a9fc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Waterford 10/10 Exceptional (12) "The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorie M. £241 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.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) ![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4bd4eab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8ea39820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Hampton Bays 10/10 Exceptional (12) "This is a simple house with a great view right on the water. The beds and bedding were comfortable. Despite being on the water, it has a nice yard and little beach area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Coleman H. £937 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/691fdd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/909788b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils, spices](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/b6de66d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Old Lyme 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lylian £151 includes taxes & fees 22 Nov - 23 Nov [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/f7b0c3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/669e9fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/8aa6190f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0c0a866f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Old Lyme 10/10 Exceptional (3) "We were very comfortable during our stay. The amenities at the house and in the vicinity were great. Our hosts were very responsive in answering our questions. We watched the World Series on the large screen TV in the den. All the family members we had stay with us during the week had ample space to sleep and stretch out. We loved the Yoga studio too. Many thanks!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole B. £313 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/1c55c50b.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/ca71fb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/544c1919.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/d4679987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Waterford 10/10 Exceptional (10) "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. £280 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.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) ![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/a0e54ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/623abb73.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) ### Holiday Home in Westbrook 10/10 Exceptional (1) "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. £383 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/53aab435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/ffda393d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/6fccc75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/f9f66e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Old Lyme 9.6/10 Exceptional (52) "Great stay, charming cottage, hope to return" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen C. £195 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information) ![One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fd0f941b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/fa3ad3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/a9bb02b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Condo King with Ocean view | Beach/ocean view](https://images.trvl-media.com/lodging/119000000/118950000/118940400/118940366/173765ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Montauk £503 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Montauk-Hotels-Offshore-Residences.h118940366.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/1c33ad63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/d9d72b46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/ca0fd6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/f3beb059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Westbrook Center 9.4/10 Exceptional (14) "Very nice small place to stay by the beach and close to great coffee shop. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donovan V. £323 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Westbrook-Hotels-Adorable-Cottage.h99406822.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) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.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) ### Holiday Home in East Hampton 9.0/10 Wonderful (4) "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. £710 includes taxes & fees 24 Nov - 25 Nov [](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/67000000/66480000/66472400/66472313/47172b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/02ffbf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/1483cc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/6ca48340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Hampon Bays 9.6/10 Exceptional (22) "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. £988 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/3067f697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Clinton 9.2/10 Wonderful (36) "Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle £140 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/8c60ece7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/f4c65ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Clinton 10/10 Exceptional (1) "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. £236 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/ea0aa1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c4ddd562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c4febed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/992d88e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Greenport 10/10 Exceptional (1) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. £418 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/a3e46cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Old Saybrook Center 9.6/10 Exceptional (38) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. £396 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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=2025-12-03&endDate=2025-12-04®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Holiday-Rentals.d157359.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Holiday-Rentals.d157359.Travel-Guide-HolidayRentals) ## Top Shelter Island Hotel Reviews ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Great" [](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.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 "amenities clean room with turndown service " [](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg) ### Sag Harbor Inn 10/10 Excellent "Great room, with a great view" [](https://expedia.co.uk/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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 "The reception staff was extremely helpful with referring our party to restaurants! Place was immaculate! Loved it - we will be back!" [](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg) ### Madison Beach Hotel 10/10 Excellent "Great 1st wedding anniversary experience!" [](https://expedia.co.uk/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful and unique property. We really enjoyed our weekend getaway " [](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 10/10 Excellent "Location - beautiful view " [](https://expedia.co.uk/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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 "Amazing experience." [](https://expedia.co.uk/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Sea Crest Resort](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Location. Staff. Space. " [](https://expedia.co.uk/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ## Find out more about Shelter Island **Everything you need to know about** **Shelter Island** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Shelter Island holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as £135 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Shelter Island rentals** At Expedia, we put the best Shelter Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Can I find holiday rentals in Shelter Island? > Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area. ### How many holiday rentals are there in Shelter Island? > Choose from 84 Expedia holiday rentals in Shelter Island for a memorable holiday. ### What can I see and do in Shelter Island? > Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Mashomack Preserve are other places to visit while you're in town. ### What are holiday rentals like in Shelter Island? > Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)