Title: Holiday Rentals Shelter Island from £131: 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) ![View of Dering Harbor](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brian V. Rowe # 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 [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2026-05-01&endDate=2026-05-03&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 rentals ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Montauk [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) 9.2/10 Wonderful (1280) "Very beautiful place, staff are amazing. Thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank £131 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.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) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/9371eb14.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) ### Apartment in Old Lyme [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) 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 £147 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.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) ![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Water Mill [](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information) 10/10 Exceptional (6) "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. £5,586 includes taxes & fees 7 Jan - 8 Jan [](https://www.expedia.co.uk/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.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) ![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/14ad38a9.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/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Clinton [](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) 9.2/10 Wonderful (36) "Many local restaurants near by. Christy's for breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin H. £134 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.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) ![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0c0a866f.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) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/4ed75f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Old Lyme [](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) 10/10 Exceptional (5) "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. £306 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/40dd49e1.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) ### Cottage in Hampton Bays [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) 10/10 Exceptional (1) £326 includes taxes & fees 12 Jan - 13 Jan [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.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) ![Exterior](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/5860a5b4.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) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/544c1919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Waterford [](https://www.expedia.co.uk/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information) 10/10 Exceptional (11) "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. £279 includes taxes & fees 15 Jan - 16 Jan [](https://www.expedia.co.uk/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.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/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/32bb5853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in East Lyme [](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) 9.0/10 Wonderful (4) "This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah G. £277 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/a34caa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/89e5a275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107780000/107779100/107779041/8613ee04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Clinton [](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information) 10/10 Exceptional (3) "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. £402 includes taxes & fees 13 Jan - 14 Jan [](https://www.expedia.co.uk/Clinton-Hotels-The-Cozy-Glass-House.h107779041.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/47172b27.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) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/02ffbf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Hampon Bays [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) 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. £1,009 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.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 dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.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) ### Holiday Home in East Hampton [](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) 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. £837 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.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) ![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) ![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Westbrook [](https://www.expedia.co.uk/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) 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. £386 includes taxes & fees 21 Jan - 22 Jan [](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/106000000/105360000/105355600/105355576/6111fd06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/a5732811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/37bca755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105360000/105355600/105355576/4af5d7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in East Lyme [](https://www.expedia.co.uk/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information) 10/10 Exceptional (9) "It was PERFECT way to spend USCGA Parent’s Weekend!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerri G. £301 includes taxes & fees 12 Jan - 13 Jan [](https://www.expedia.co.uk/Niantic-Hotels-Quaint-Beach-Cottage.h105355576.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/aeb85212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/126bef9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Home in Sag Harbor [](https://www.expedia.co.uk/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) £4,845 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.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) ![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) ![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) ### Holiday Home in Hampton Bays [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) 9.6/10 Exceptional (14) "Nice house. Photos and descriptions represent it very accurately. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Will K. £961 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/645209f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/56a6cc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/e4b9a917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106310000/106307100/106307058/c1b7f88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Old Lyme [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Bridge-At-Soundview-BeachOceanViewSunrise.h106307058.Hotel-Information) 10/10 Exceptional (2) "The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emotional J. £370 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Bridge-At-Soundview-BeachOceanViewSunrise.h106307058.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) ![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) ![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) ### Cottage in Greenport [](https://www.expedia.co.uk/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) 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. £384 includes taxes & fees 8 Jan - 9 Jan [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/71856d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Old Saybrook Center [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) 9.6/10 Exceptional (41) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. £398 includes taxes & fees 7 Jan - 8 Jan [](https://www.expedia.co.uk/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/d9d72b46.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 [](https://www.expedia.co.uk/Westbrook-Hotels-Adorable-Cottage.h99406822.Hotel-Information) 9.4/10 Exceptional (15) "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 7 Jan - 8 Jan [](https://www.expedia.co.uk/Westbrook-Hotels-Adorable-Cottage.h99406822.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/1ce6739a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/6c064ac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/bddecfe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/6b05e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Old Lyme [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.Hotel-Information) 8.0/10 Very good (2) "So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) October P. £147 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.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=2026-01-20&endDate=2026-01-21®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 Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Everything was Great Immaculate hotel very good location sraff was great" [](https://expedia.co.uk/Greenport-Hotels-The-Harborfront-Inn.h43532300.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 "All was beautiful" [](https://expedia.co.uk/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Always an ama" [](https://expedia.co.uk/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg) ### Offshore Montauk 10/10 Excellent "Always a great stay" [](https://expedia.co.uk/Montauk-Hotels-The-Offshore.h113578409.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 "The rooms were so nice! Definitely gonna be back!" [](https://expedia.co.uk/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "The room was much larger than expected, very clean. Perfect location, Melissa at the front desk was very helpful" [](https://expedia.co.uk/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.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 "Excellent " [](https://expedia.co.uk/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great place!" [](https://expedia.co.uk/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg) ### Montauk Manor 10/10 Excellent "We gave stayed at Montauk Manor for the holiday for many years. The lobby area is grand and very festive during the holidays. The units are clean and comfortable with amenities that make it easy to eat in if desired. The front desk staff are helpful and friendly and the in house restaurant, Montes, is wonderful. We will continue to come on holidays! It is a special place. " [](https://expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.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 £131 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? ### What are some of the best holiday rentals that Shelter Island has to offer? ### How many holiday rentals are there in Shelter Island? ### What can I see and do in Shelter Island? ### What are holiday rentals like in Shelter Island? ![](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. 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