Title: Shelter Island Vacation Rentals from $166: Search Short-Term Rentals | Expedia.com [Shelter Island Travel Guide](https://expedia.com/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Flights to Shelter Island](https://expedia.com/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Car Rentals in Shelter Island](https://expedia.com/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.com/Shelter-Island.d157359.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-07-24&endDate=2026-07-26&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 vacation rentals ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.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) ![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom cottage with Grove Beach 🏖️ access. [](https://www.expedia.com/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) Clinton 9.6/10 Exceptional (40 reviews) "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. $166 nightly $188 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.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/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/035b4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk [](https://www.expedia.com/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information) Waterford 10/10 Exceptional (18 reviews) "Wonderful place with a great location! Fantastic communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cary H. $266 nightly $301 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/4e5920d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bay Cottage · Rocky Neck Park, Beach & Niantic [](https://www.expedia.com/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) East Lyme 9.0/10 Wonderful (4 reviews) "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. $405 nightly $458 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/116c6f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/fcccb3b4.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/107000000/106150000/106148000/106147917/2c60a89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/2c178ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Anchor at Soundview · Beach+Ocean+Sunrise [](https://www.expedia.com/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.Hotel-Information) Old Lyme 8.0/10 Very Good (2 reviews) "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. $172 nightly $194 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/bec199ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0298db95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/9ddc24ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rogers Lake House (87) · CT College+Beach+USCGA [](https://www.expedia.com/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) Old Lyme 10/10 Exceptional (6 reviews) "Host was very responsive. Property as described. We would stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john18250 $394 nightly $445 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information) ![Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f0c0c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/b50e5baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Tent, 1 Queen Bed | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/fe9ed1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort [](https://www.expedia.com/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) Greenport 8.6/10 Excellent (11 reviews) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin $183 nightly $209 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/3f2f736d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/2d4d8efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b42f892a.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/ab165773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze 3 Cozy cottage by the beach [](https://www.expedia.com/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) Hampton Bays 10/10 Exceptional (1 review) $435 nightly $463 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/33a85d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/8066b18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/fda79bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4ad42a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks [](https://www.expedia.com/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information) Waterford 10/10 Exceptional (11 reviews) "Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda W. $401 nightly $453 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c88122e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/9825549c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/ef7e518d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/1e415396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BlackBerry Private home with jacuzzi yearlong [](https://www.expedia.com/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) East Hampton 9.0/10 Wonderful (4 reviews) "We had a great time staying here. The home is well worn and there are some fixtures that should be replaced " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne R. $747 nightly $800 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/3dd02542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/9b931aba.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) ![West Studio Queen and Full | Living area | TV](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/fcfe3def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windward Shores Ocean Resort [](https://www.expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) Napeague 8.8/10 Excellent (310 reviews) "Amazing stay! Place was perfect and staff was so friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather $172 nightly $197 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.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) ### Montauk Manor [](https://www.expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) Montauk 9.2/10 Wonderful (1,309 reviews) "Great property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) brian $168 nightly $192 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/c3f938dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/72873cc1.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) ![Exterior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/ffda393d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Insta-worthy Couples Retreat: Perfect for romantic getaway! [](https://www.expedia.com/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information) Old Lyme 9.4/10 Exceptional (53 reviews) "Adorable cottage. Nice location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet B. $236 nightly $267 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a433371c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a3f762f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/9aa58e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/4235c401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Luz Cozy Family Home with Jacuzzi year round [](https://www.expedia.com/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) Hampon Bays 9.6/10 Exceptional (23 reviews) "Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie B. [](https://www.expedia.com/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/e12e0a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ce1cf8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a85d3539.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) ### Shoreline Oasis [](https://www.expedia.com/Shoreline-Oasis.h113308197.Hotel-Information) Clinton 9.2/10 Wonderful (7 reviews) "Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom S. $257 nightly $291 total Apr 4 - Apr 5 Total with taxes and fees [](https://www.expedia.com/Shoreline-Oasis.h113308197.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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/e3540489.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) ### Floating Nest on Private River. Serene Views & Ultimate Relaxation [](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information) Old Lyme $330 nightly $374 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/6d467d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/d00906f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/a7c4d35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/8e03b24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamptons apartment getaway [](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information) East Quogue 6.0/10 (3 reviews) "The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hilary K. $249 nightly $284 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/8aaee58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/bb209788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/29a6f4b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/fc0e0719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included [](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information) Westbrook Center $228 nightly $259 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information) ![Condo | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.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/a48d2d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/c4e4571c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/0090e01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliffside Resort Condominiums [](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) Greenport 9.0/10 Wonderful (249 reviews) "Great stay - beautiful place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca $182 nightly $208 total Apr 29 - Apr 30 Total with taxes and fees [](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Bliss w/ Game Room, Gym & Golf Green [](https://www.expedia.com/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) Westbrook 10/10 Exceptional (1 review) "Perfect house for 6 guests. Loved that it was close to the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon G. $468 nightly $530 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/1bd85de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/73000000/72610000/72604700/72604611/6b6b7167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds [](https://www.expedia.com/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) Old Saybrook Center 9.6/10 Exceptional (43 reviews) "Lovely cottage! Enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce S. $474 nightly $537 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14®ionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=VILLA) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-28&d1=2026-06-28&endDate=2026-07-01&d2=2026-07-01&lodging=HOUSE_BOAT) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals) ## Top Shelter Island Hotel Reviews ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 6/10 Okay "Room could have been cleaner. The floor was dirty. The room also looked worn and in need of updating. The tub faucet dripped constantly, but the shower was nice. Staff was friendly. I was surprised they don’t offer daily housekeeping. Bed was comfortable. It was great that the room had a microwave and a fridge. It was not warm and inviting at all. Definitely wouldn’t stay more than one night." [](https://expedia.com/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Simply delightful!" [](https://expedia.com/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg) ### Offshore Montauk 10/10 Excellent "Nice clean room. Updated. Amazing staff. Small and not much storage or bathroom counter but very nice room. " [](https://expedia.com/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0_y.jpg) ### Sag Harbor Inn 10/10 Excellent "Clean rooms, very warming atmosphere " [](https://expedia.com/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e_y.jpg) ### The Sagaponack 10/10 Excellent "Wonderful! What a beautiful property, room and the location is perfection!" [](https://expedia.com/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "We loved our stay!" [](https://expedia.com/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Enjoyable stay. " [](https://expedia.com/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg) ### Montauk Manor 10/10 Excellent "Went for a quick one both stay with my kids to go hiking. We picked this place because they had a pool. Everything was clean and nice. The rooms were cool the kids loved it " [](https://expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "Absolutely beautiful property- laid back but classically tasteful. Staff was wonderful…Mimmeo & Sebastian are fabulous & friendly & Ivette in the spa gave a top notch massage. Gigi’s never disappointed! I will absolutely be back. " [](https://expedia.com/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ## Find out more about Shelter Island **Everything you need to know about Shelter Island vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Shelter Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Shelter Island rentals** At Expedia, we put the best Shelter Island vacation 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 vacation. 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.com - All accommodation types in Shelter Island ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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[Vacation Homes in Shelter Island ](https://expedia.com/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Shelter Island ](https://expedia.com/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation) - [Apartments in Shelter Island ](https://expedia.com/Shelter-Island-Apartments.d157359-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Shelter Island ](https://expedia.com/Shelter-Island-Condos.d157359-aaCondos.Travel-Guide-Accommodation) - [Villas in Shelter Island ](https://expedia.com/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation) - [B&B in Shelter Island ](https://expedia.com/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Shelter Island ](https://expedia.com/Shelter-Island-Motels.d157359-aaMotels.Travel-Guide-Accommodation) - [Resorts in Shelter Island ](https://expedia.com/Shelter-Island-Resorts.d157359-aaResorts.Travel-Guide-Accommodation) - [RV Parks in Shelter Island ](https://expedia.com/Shelter-Island-RV-Parks.d157359-aaRVParks.Travel-Guide-Accommodation) - [Aparthotels in Shelter Island ](https://expedia.com/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation) - [Farmstay in Shelter Island ](https://expedia.com/Shelter-Island-Agritourism.d157359-aaAgritourism.Travel-Guide-Accommodation) - [Inns in Shelter Island ](https://expedia.com/Shelter-Island-Inns.d157359-aaInns.Travel-Guide-Accommodation) - [Houseboats in Shelter Island ](https://expedia.com/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation) - [Guest Houses in Shelter Island ](https://expedia.com/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation) - [Cabin Rentals in Shelter Island ](https://expedia.com/Shelter-Island-Cabins.d157359-aaCabins.Travel-Guide-Accommodation) - [Chalets in Shelter Island ](https://expedia.com/Shelter-Island-Chalets.d157359-aaChalets.Travel-Guide-Accommodation) - [Hostels in Shelter Island ](https://expedia.com/Shelter-Island-Hostels.d157359-aaHostels.Travel-Guide-Accommodation) - [Lodges in Shelter Island ](https://expedia.com/Shelter-Island-Lodges.d157359-aaLodges.Travel-Guide-Accommodation) - [Condo Resorts in Shelter Island ](https://expedia.com/Shelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation) - [Residences in Shelter Island ](https://expedia.com/Shelter-Island-Residences.d157359-aaResidences.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find vacation rentals in Shelter Island? ### What are some of the best vacation home rentals that Shelter Island has to offer? ### How many vacation rentals are there in Shelter Island? ### What can I see and do in Shelter Island? ### What are vacation rentals like in Shelter Island? ### Expedia's Latest Trends Hotels - [Hotels in Montauk](https://expedia.com/Montauk-Hotels.d10637.Travel-Guide-Hotels) - [Hotels in Lake Placid](https://expedia.com/Lake-Placid-Hotels.d6055989.Travel-Guide-Hotels) - 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