Title: Holiday Rentals Shelter Island from £121: 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) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by tom owens # Search Holiday Rentals in Shelter Island ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=157359&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Shelter Island ![Ocean View 2BD Corner King and Queen | Living area | TV](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/213ea8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/700cd038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2BD Corner King and Queen | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/5974dc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windward Shores Ocean Resort Amagansett 8.8/10 Excellent (296) "Very nice & affordable " [](https://www.expedia.co.uk/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.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) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor Montauk 9.2/10 Wonderful (1252) "Beautiful grounds, excellent staff" £121 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Apartment | Private kitchen | Fridge, microwave, stovetop](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/4604b12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/026ba813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Private kitchen | Fridge, microwave, stovetop](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/e03ad839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Private kitchen | Fridge, microwave, stovetop](https://images.trvl-media.com/lodging/12000000/11070000/11062900/11062836/4c252ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Oceanside Suites Montauk 8.6/10 Excellent (414) "We loved it, suite size was great! " £123 includes taxes & fees 20 Oct - 21 Oct [](https://www.expedia.co.uk/Montauk-Hotels-Born-Free-Suites-By-The-Sea.h11062836.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/w1446h1293x1y0-077b519e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/d9295239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliffside Resort Condominiums Greenport 9.0/10 Wonderful (241) "Great view of the water and nice amenities with the beach and pool." £222 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![On the beach, white sand](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/1ba7bf71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/5f3d4968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtside Two Bedroom | 1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/1c56664c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Ocean View | 1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207128/f8e91815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Surf Club Montauk 8.6/10 Excellent (278) "Very close walk to the beach great for little ones " [](https://www.expedia.co.uk/Montauk-Hotels-The-Surf-Club.h4207128.Hotel-Information) ![Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/59e33701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/d8406ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/6b2173cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/14ba9bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Resort Montauk 9.0/10 Wonderful (235) "Great place to stay for small family " £146 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Montauk-Hotels-Driftwood-Resort.h4207142.Hotel-Information) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/20bccc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/ca35c4da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/9341740d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/27000000/26560000/26554100/26554014/95829c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill Montauk 8.8/10 Excellent (28) "This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!... [](https://www.expedia.co.uk/Montauk-Hotels-Oceanfront.h26554014.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/05048f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/67d18d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, ping pong, books, stereo](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/70e808a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101880000/101877700/101877657/dc64ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping Southampton 9.8/10 Exceptional (32) "Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!" [](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/c1c14546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/9a2f74fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/200490ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105954000/105953994/b0e8e3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor Bridgehampton 9.6/10 Exceptional (15) "Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!" £298 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Bridgehampton-Hotels-Cozy-Bungalow-Available-Nearby-Bridgehampton-And-Sag-Harbor.h105953994.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c0b20841.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/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk Waterford 10/10 Exceptional (9) "This listing was perfect for our stay. Close to the water, beautifully styled, and plenty of items to cook and clean.Thanks so much, Erin!" £247 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Waterford-Hotels-Charming-3-Bedroom-Cottage-With-WiFi.h108765994.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a7476bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/1f01f033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ea540de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shoreline Oasis Clinton 9.2/10 Wonderful (7) "A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!" £199 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Clinton-Hotels-Shoreline-Oasis.h113308197.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/69c78126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/e5e7798f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/46ba0f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, electric kettle, toaster](https://images.trvl-media.com/lodging/105000000/104810000/104804300/104804253/3a51fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy houseboat escape surrounded by breath taking views across from Rocky Neck! Old Lyme 10/10 Exceptional (13) "Such a fun, beautiful and unique stay. Would love to stay again!" £228 includes taxes & fees 6 Oct - 7 Oct [](https://www.expedia.co.uk/Old-Lyme-Hotels-Cozy-Houseboat-Escape-Surrounded-By-Breath-Taking-Views-Across-From-Rocky-Neck.h104804253.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/ee3ffaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/eb892682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/43458864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33090000/33088400/33088314/ec9d9a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town! Montauk 9.8/10 Exceptional (96) "Very Nice stay there for business would go back for pleasure" [](https://www.expedia.co.uk/Montauk-Hotels-Newly-Renovated-Montauk-Oceanfront-Condo-Steps-To-Beach.h33088314.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/d31ec06c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/ef304302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/66e0afe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70110000/70101200/70101127/57b353a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play! Westbrook Center 10/10 Exceptional (7) "We enjoyed our time in Westbrook! Hosts were more than accomodating and helpful throughout our stay - thank you! House is cute, the perfect size for a small group, and in a good location (walking distance to many shops and restaurants). Private beach access is easy to get to (beach area is small, but it worked!)" [](https://www.expedia.co.uk/Westbrook-Hotels-Perfect-Shoreline-Stay-Walk-To-Beach.h70101127.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/ec19dfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/9f7825c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/03847a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/55000000/54250000/54242900/54242867/de3f6f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairy Tale Guest Cottage in Magic Garden by Pool Bridgehampton 10/10 Exceptional (75) "We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. " [](https://www.expedia.co.uk/Bridgehampton-Hotels-Fairy-Tale-Guest-Cottage-In-Magic-Garden-By-Pool.h54242867.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/4c400fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun-loungers](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/bf812e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/270-800f5613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32530000/32523000/32522969/ad085255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MONTAUK MANOR-DELUXE STUDIO APARTMENT MONTAUK 9.8/10 Exceptional (74) "We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! " [](https://www.expedia.co.uk/Montauk-Hotels-MONTAUK-MANOR-DELUXE-STUDIO-APARTMENT.h32522969.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ca104a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/b05e12cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/850fe737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ae5634ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom! Hampton Bays 9.6/10 Exceptional (137) "Perfect property to hangout and stay entertained for hours" [](https://www.expedia.co.uk/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/077d4275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dfbac7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/dcee1147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/35000000/34210000/34201400/34201329/7757c331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 'The Gate House'on Beach front Estate with Dockage. Walk to Village . Pipes Cove 9.8/10 Exceptional (99) "My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town." [](https://www.expedia.co.uk/Greenport-Hotels-The-Gate-Houseon-Beach-Front-Estate-With-Dockage-Walk-To-Village.h34201329.Hotel-Information) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/1e7208b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/13c2a30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/572bf9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/34000000/33500000/33492900/33492827/3c58e4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready Montauk 10/10 Exceptional (105) "Very walkable charming stay in beautiful area that supports larger group. Carter is very responsive and friendly. " [](https://www.expedia.co.uk/Montauk-Hotels-Private-Montauk-Setting-Walk-To-Beach-Town-Large-Pool-Jacuzzi-Kid-Friendly.h33492827.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/5b4c06e7.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) ### The Stern at Soundview · Beach+Ocean+Sunrise Old Lyme 10/10 Exceptional (3) "I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! " £128 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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=2025-10-18&endDate=2025-10-19®ionId=157359&adults=2&sort=RECOMMENDED&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 ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Beautiful grounds, well maintained property. Our room was clean and comfortable. Definitely want to come back and extend our stay with family and friends. It’s a beautiful escape on the East Coast " [](https://expedia.co.uk/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Sun N Sound](//images.trvl-media.com/lodging/5000000/4230000/4225500/4225489/5de1d3d0_y.jpg) ### Sun N Sound 10/10 Excellent "Stayed here for one night. The room was very clean and the view was beautiful." [](https://expedia.co.uk/Montauk-Hotels-Sun-N-Sound.h4225489.Hotel-Information) ![The Sagaponack](//images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "I arrived late night for check-in. The staff text arranged for checking me in ahead of time and left a nice breakfast for me for the morning. Thank you!" [](https://expedia.co.uk/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" [](https://expedia.co.uk/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Montauk Blue Hotel](//images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg) ### Montauk Blue Hotel 10/10 Excellent "The ocean view from the 2nd floor was beautiful. The area was very walkable, but it was still nice to have a car to explore other areas such as the light house. Room was clean and staff was helpful. " [](https://expedia.co.uk/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg) ### Offshore Montauk 10/10 Excellent "The staff is excellent and very accommodating. Great place in a great location. Would stay here again." [](https://expedia.co.uk/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Beachcomber Resort at Montauk](//images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Beautiful room right across from the ocean and by town. Definitely go back!" [](https://expedia.co.uk/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities" [](https://expedia.co.uk/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Perfect location!" [](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 £121 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. ### What are some of the best holiday rentals that Shelter Island has to offer? > [Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping](https://www.expedia.co.uk/Southampton-Hotels-Delightful-Southampton-Retreat-With-Heated-Pool-Jacuzzi.h101877657.Hotel-Information): This holiday home rental outside of Shelter Island offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. ### How many holiday rentals are there in Shelter Island? > Choose from 85 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. Mashomack Preserve and Gardiner's Bay Country Club 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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)