Title: Book The Best Hotels in Shelter Island, NY for 2025 from CA $128 - Compare prices by date | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Shelter Island, NY from CA $128 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.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 Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Shelter Island Spa [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=SPA_ON_SITE) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=OCEAN_VIEW) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=HOT_TUB) Pool [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=POOL) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&lodging=APARTMENT) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&travelerType=family_friendly) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=PETS) Condo [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&lodging=CONDO) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America®ionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2025-10-15&d1=2025-10-15&endDate=2025-10-17&d2=2025-10-17&amenities=WATER_PARK) ## Check prices for these dates Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 4,702 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![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) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen](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) ### Montauk Manor Montauk 9.2/10 Wonderful (1251) "Beautiful grounds, excellent staff" CA $180 CA $232 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/f7da52a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/8957afe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saybrook Point Resort & Marina Old Saybrook Center 9.4/10 Exceptional (1000) "Great place!! " CA $383 CA $476 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View One Bedroom Suite](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/d3ce4464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Two Bedroom Suite | Living area](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/60539ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront One Bedroom Suite | Terrace/patio](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/3a4c2dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gurney's Montauk Resort & Seawater Spa Montauk 8.2/10 Very good (669) "Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. " CA $430 CA $588 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio (Upper Level Corner)](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/25e00712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (Lower Level) | Living area](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/6cdd0286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Fireplace | Living area](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/7f15eb82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachcomber Resort at Montauk Montauk 9.4/10 Exceptional (597) "Lovely stay and great staff! " CA $242 CA $318 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![Deluxe Double Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/e3ee1fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Bays Hotel on Main Hampton Bays 7.0/10 Good (61) "Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!" CA $159 CA $182 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pier Blue Inn Old Saybrook - Essex Saybrook Manor 7.8/10 Good (1001) "Very friendly and helpful staff." CA $112 CA $128 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/55438f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Atlantic Hotel Southampton 7.2/10 Good (944) "Very nice staff and great location " CA $162 CA $219 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/7bd2ac6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/8593ea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/1443e1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/67609737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Surf Resort Montauk 8.4/10 Very good (208) "The view from our balcony was beautiful! We watched whales and dolphins swim by. Hotel is close to restaurants and town and very walkable. Would definitely stay again " CA $165 CA $189 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-Ocean-Surf-Resort.h12001193.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View King](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/e47e67f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk Montauk 9.2/10 Wonderful (54) "The staff is excellent and very accommodating. Great place in a great location. Would stay here again." CA $205 CA $394 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard Double Queen](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/07fb7947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/00b9aef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/b1a067ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marram Montauk 8.8/10 Excellent (230) "We loved everything about our stay here: the beds are comfortable, the fire pits with the smores are a nice touch, the beach is very nice, the view as well; and the food is amazing. The staff is very helpful and friendly!" CA $282 CA $450 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/9f1bca91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/74fca349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/34576327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hampton Maid Hampton Bays 9.0/10 Wonderful (663) "Great place to stay" CA $262 CA $299 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Maid-Motel.h19715959.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/5c6281d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/533d1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Multiple Beds, Ground Floor (by the Sea) | Beach/ocean view](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/25adc215.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water's Edge Resort & Spa Westbrook Center 8.8/10 Excellent (1021) "clean and quiet property, great views, amazing staff" CA $303 CA $373 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Harbor View Balcony Junior Suite | Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/e407cc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (521) "Great location ,beautiful hotel,nice staff" CA $230 CA $331 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/511d84f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook Old Saybrook 7.6/10 Good (1001) "We have stayed there before so have been pleased with it." CA $130 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/20957ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/bfb5cc4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/dc9e5678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zey Hotel Greenport 9.2/10 Wonderful (275) "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." CA $366 CA $419 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a7102e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (257) "Staff was amazing and this hotel is in the perfect location " CA $193 CA $221 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/fc8f49f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/7454864c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/98ce732d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vista Resort Amagansett 9.0/10 Wonderful (194) "Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!" CA $187 CA $213 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1011) "Wonderful hotel and location " CA $271 CA $468 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/1f765cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/783d70b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/6a60f683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/22000000/21830000/21825900/21825843/cd124626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Preston House & Hotel Riverhead 9.8/10 Exceptional (363) "Pet friendly " CA $316 CA $361 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Riverhead-Hotels-The-Preston-House-Hotel.h21825843.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/949a0d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (315) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." CA $175 CA $200 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.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.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17®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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShelter-Island-Hotels.d157359.Travel-Guide-Hotels) ## Where to stay in Shelter Island Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. [Learn more about Shelter Island](https://www.expedia.ca/Shelter-Island.dx157359) - Menantic Creek - Silver Beach - Coecles Harbor - Hay Beach - Shorewood [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481214) ![Menantic Creek map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7BryFh%7CqxLeOkr%40fT_EnMqEjKc%40fGjBhAuArItErIPrBlB%7DAd%5Cm_AnW&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=n26EkDMTtXxMOW9v2XNlupnSUzc=) ### Menantic Creek If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481214) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481903) ![Silver Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mzpyF%60vvxLg%60%40kEi%40%7DHuLaYrBOSaK_Oib%40n%40cFuWiStCmEvBXxDwDfHH%7EK%60NpNxDjFyGlHrAf%5CwSlg%40oUhImBpAvPoN%7El%40kp%40dsAcAxK&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=LI215i5nbJyDKLk8XZgKcAhItxY=) ### Silver Beach While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481903) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976480820) ![Coecles Harbor map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ybxyFxymxLw%5Das%40rjAyyBnqA%7Cx%40pIl%7E%40%7DhCnt%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=xFWty9iq-ZDYNo-RgTcjrckcozE=) ### Coecles Harbor When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Mashomack Preserve, some noteworthy sights in the nearby area. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976480820) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976470037) ![Hay Beach map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:q%7DyyFvxoxLu%7B%40aS%7Ei%40owAnj%40cEfEdc%40a_%40nmA&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=oUw1-B9agSYZdTPReexAj0cx418=) ### Hay Beach Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976470037) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=553248635976481937) ![Shorewood map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:iepyFdhnxLeP%7DEuBi%5Cfa%40wNvL%7BLRhb%40cTnSsE%60I&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wv_xANliD00Fd1ruzPgVjStzT-s=) ### Shorewood While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Sunset Beach. [See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976481937) ## Learn more about Shelter Island Escape to Shelter Island! Enjoy its island views, natural setting, and beaches. [See all hotels in Shelter Island](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&adults=2®ionId=157359) ![](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by tom owens ### Stay near popular Shelter Island attractions [](https://expedia.ca/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels) #### Gardiner's Bay Country Club Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6282173) [](https://expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) #### Shelter Island Whale's Tail You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204762) [](https://expedia.ca/Mashomack-Preserve-Hotels.0-l6224462-0.Travel-Guide-Filter-Hotels) #### Mashomack Preserve Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6224462) [](https://expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels) #### Wades Beach Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204759) [](https://expedia.ca/Shell-Beach-Hotels.0-l553248621554204761-0.Travel-Guide-Filter-Hotels) #### Shell Beach Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621554204761) [](https://expedia.ca/Shelter-Island-Historical-Society-Hotels.0-l553248635961235094-0.Travel-Guide-Filter-Hotels) #### Shelter Island Historical Society You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635961235094) ## More cheap stays in Shelter Island ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Atlantic Hotel 1655 County Road 39, Southampton, NY CA $162 CA $219 total Nov 2 - Nov 3 includes taxes & fees 7/10 Good! (944 reviews) [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd, Old Saybrook, CT CA $112 CA $128 total Oct 6 - Oct 7 includes taxes & fees 7.8/10 Good! (1,001 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Greenporter Hotel](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Greenporter Hotel 326 Front St, Greenport, NY CA $193 CA $221 total Oct 8 - Oct 9 includes taxes & fees 9.2/10 Wonderful! (256 reviews) [](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Bentley Hotel Southampton 161 Hills Station Rd, Southampton, NY CA $222 CA $254 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (343 reviews) [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Old Saybrook - Westbrook 100 Essex Rd, Old Saybrook, CT CA $130 CA $150 total Nov 2 - Nov 3 includes taxes & fees 7.6/10 Good! (1,011 reviews) [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Montauk Blue Hotel 108 South Emerson Avenue, Montauk, NY CA $201 CA $230 total Nov 2 - Nov 3 includes taxes & fees 9.2/10 Wonderful! (145 reviews) [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ## Find out more about Shelter Island ### Top reasons to visit Shelter Island - **Stunning Beaches:** Shelter Island boasts beautiful beaches like Crescent Beach, perfect for relaxation and ocean views. - **Outdoor Adventures:** Enjoy paddle boarding, windsurfing, and golf amidst the island's natural beauty. - **Rich History:** Explore historic buildings and learn about the island's unique heritage. - **Scenic Boat Tours:** Take a picturesque boat tour to appreciate the stunning coastal scenery. - **Diverse Accommodations:** Choose from pet-friendly and family-oriented stays to suit every traveller's needs. ### Find great hotels near Shelter Island Experience the charm of Shelter Island with a variety of accommodations tailored to meet the needs of every traveller. From pet-friendly options to family-oriented stays, you'll find the perfect lodging for your adventure. Explore the best hotels and luxury accommodations that provide a memorable vacation experience amidst the beautiful surroundings of Shelter Island. - **[Sound View Greenport:](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)** Nestled 6.4km from Shelter Island, Sound View Greenport is a delightful 3.5-star hotel that combines a business-friendly environment with a family-oriented beach getaway. Guests can enjoy direct access to the pristine beach, perfect for sun-soaked days. The hotel is equipped with essential business amenities, including meeting rooms and conference spaces, ensuring a productive stay for corporate travellers. Families will appreciate thoughtful features such as window guards for children and complimentary cribs, making it a safe and enjoyable destination for all ages. - **[Sag Harbor Inn:](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)** Located 8.0km from Shelter Island, Sag Harbor Inn offers a sophisticated 3.5-star experience tailored for business travellers. This charming inn provides essential business facilities, including meeting rooms, allowing guests to conduct meetings in a serene setting. The inn's proximity to both the vibrant town of Sag Harbor and the scenic waterfront makes it an appealing choice for those looking to blend work and leisure. The inviting atmosphere and convenient amenities make it a great option for a productive yet relaxing stay. - **[The Harbor Front Inn:](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)** Situated 4.8km from Shelter Island, The Harbor Front Inn is a welcoming 3.5-star hotel that prides itself on being pet-friendly. Ideal for business travellers who wish to bring their furry companions along, the inn features a pet policy that allows dogs in guest rooms. With a focus on comfort and convenience, guests can enjoy business amenities while also having the flexibility to travel with their pets. The charming waterfront location enhances the appeal, ensuring a delightful retreat for both you and your four-legged friends. ### Where to stay near Shelter Island Discover the charm of Shelter Island, a perfect getaway for outdoor enthusiasts and couples alike. Enjoy stunning ocean views and relaxing beach access at Crescent Beach. Explore the rich history of the area while immersing yourself in its family-friendly atmosphere. Nearby Long Island offers additional excursions and scenic spots, making Shelter Island an ideal base for your vacation adventure. Experience the unique blend of relaxation and exploration that this picturesque destination has to offer. - **[Hamptons:](https://www.expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)** Located 14.5km from Shelter Island, the Hamptons is a quintessential summer retreat known for its stunning beaches and vibrant atmosphere. This area is particularly popular from June to August, attracting visitors for its romantic seaside charm and outdoor activities. With picturesque golf courses and lively music concerts, the Hamptons offers an array of entertainment options. Local landmarks like beautiful beaches and serene lakes provide the perfect backdrop for relaxation and adventure alike, making it an ideal spot for those looking to soak up the sun and enjoy coastal life. - **[Greenport:](https://www.expedia.ca/Greenport-Hotels.d110728.Travel-Guide-Hotels)** Only 4.8km away from Shelter Island, Greenport boasts a charming small-town vibe combined with rich maritime history. This city, which sees a spike in visitors from June to August, is perfect for those seeking outdoor adventures, romantic getaways, and beach time. Visitors can enjoy various activities like golfing and attending local music concerts. The nearby family-friendly beaches and event conference venues add to the allure, making Greenport a delightful destination for exploration and fun. - **[Sag Harbor:](https://www.expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)** Just 8.0km from Shelter Island, Sag Harbor is a picturesque village that captures the essence of coastal living. Known for its outdoor attractions and romantic atmosphere, this city experiences peak visitor numbers in the summer months. Visitors can indulge in golfing or even skiing during the winter months. The local beaches and parks offer ample opportunities for relaxation and recreation, making Sag Harbor a charming stop for those looking to immerse themselves in the beauty of the East End. ### Things to do in and around Shelter Island Shelter Island is perfect for outdoor adventures and romantic getaways, offering a variety of activities. Enjoy paddle boarding and windsurfing on its beautiful waters, explore numerous attractions, or take a scenic boat tour. Golf enthusiasts will appreciate the island's golf courses, and there are opportunities for skiing as well. With its stunning beaches and natural beauty, Shelter Island is an ideal destination for a memorable vacation. **Shopping** The [Greenport Farmers' Market](https://www.expedia.ca/Greenport-Farmers-Market-Hotels.0-l553248621532665744-0.Travel-Guide-Filter-Hotels), located 4.8km away, offers a vibrant public market experience with local produce and crafts. [The Style Bar](https://www.expedia.ca/The-Style-Bar-Hotels.0-l553248621532665737-0.Travel-Guide-Filter-Hotels) and [BookHampton](https://www.expedia.ca/BookHampton-Hotels.0-l553248621532665731-0.Travel-Guide-Filter-Hotels), both 8.0km away, feature unique clothing and books, perfect for souvenirs. If you're up for a drive, explore further shopping options in nearby towns. **Recreation** [Shelter Island Whale's Tail](https://www.expedia.ca/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) offers a fun-filled mini-golf experience with a family-friendly atmosphere perfect for playful competition. For golf enthusiasts, [Noyac Golf Club](https://www.expedia.ca/Noyac-Golf-Club-Hotels.0-l6064499-0.Travel-Guide-Filter-Hotels) presents a picturesque outdoor course just 9.7km away. [Cedar Point County Park](https://www.expedia.ca/Cedar-Point-County-Park-Hotels.0-l6326834-0.Travel-Guide-Filter-Hotels), located 8.0km away, invites relaxation amidst nature with its tranquil surroundings. **Adventure** Experience the thrill at [Splish Splash Water Park](https://www.expedia.ca/Splish-Splash-Water-Park-Hotels.0-l6173416-0.Travel-Guide-Filter-Hotels), located 37.0km from Shelter Island, with exciting water slides and family fun. Hike the scenic [Walking Dunes Trailhead](https://www.expedia.ca/Walking-Dunes-Trailhead-Hotels.0-l553248633992587102-0.Travel-Guide-Filter-Hotels), 25.7km away, for stunning views. For adrenaline, check out the [Riverhead Raceway](https://www.expedia.ca/Riverhead-Raceway-Hotels.0-l6173429-0.Travel-Guide-Filter-Hotels), 35.4km from Shelter Island, featuring exhilarating motor racing. **Nightlife** Experience the enchanting [Greenport Carousel](https://www.expedia.ca/Greenport-Carousel-Hotels.0-l553248635961252285-0.Travel-Guide-Filter-Hotels), just 4.8km away, for a nostalgic ride under the stars. For a cultural evening, visit [Bay Street Theatre](https://www.expedia.ca/Bay-Street-Theatre-Hotels.0-l6326787-0.Travel-Guide-Filter-Hotels), 8.0km from Shelter Island, which offers a blend of romance and entertainment, perfect for families and couples alike. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Shelter Island To save money on your trip to Shelter Island, consider visiting between January and March when hotel prices are at their lowest. Tuesdays are typically the least expensive days for accommodation. Use Expedia to search for budget-friendly hotels, and don’t forget to check for eco-certified options. Additionally, bundling your hotel with flights and activities can lead to great savings. Explore free local attractions and utilize public transport to keep costs down. Planning your visit during the off-peak season and taking advantage of deals will enhance your experience without breaking the bank. - **The most and least expensive months on average to stay in a hotel:** The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking. - **Consider bundling your trip:** You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in and around Shelter Island Shelter Island offers a perfect blend of outdoor adventures, romantic getaways, and family-friendly experiences. Visitors can enjoy beautiful beaches, explore historic buildings, and relax in urban parks. With a focus on culture and leisure, popular activities include unwinding at sunset beach, making it an ideal destination for those seeking relaxation and exploration. - **[67 Steps Beach:](https://www.expedia.ca/67-Steps-Beach-Hotels.0-l553248626388140598-0.Travel-Guide-Filter-Hotels)** A picturesque beach located 6.4km from Shelter Island, 67 Steps Beach offers a serene escape with its beautiful shoreline and tranquil vibes. It's the perfect spot for sunbathing, swimming, or simply enjoying the coastal scenery. - **[Gardiner's Bay Country Club:](https://www.expedia.ca/Gardiners-Bay-Country-Club-Hotels.0-l6282173-0.Travel-Guide-Filter-Hotels)** Situated within Shelter Island, this exceptional golf course provides a unique blend of challenging play and stunning views. Experience a round of golf surrounded by lush landscapes and the refreshing breeze from the bay. - **[Orient Point County Park:](https://www.expedia.ca/Orient-Point-County-Park-Hotels.0-l553248621532665781-0.Travel-Guide-Filter-Hotels)** Located 12.9km from Shelter Island, this urban park is ideal for families and outdoor enthusiasts. Enjoy scenic trails, picnic spots, and the vibrant atmosphere of the city, making it a great place to unwind and connect with nature. ### Best time to go to Shelter Island The best time to visit Shelter Island is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 35.6°F (2.0°C) | Light Rain | Mostly Sunny | Average | Moderately Low | | February | 35.8°F (2.1°C) | Light Rain | Mostly Cloudy | Average | Moderately Low | | March | 39.7°F (4.3°C) | Light Rain | Mostly Sunny | Average | Moderately Low | | April | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Average | Average | | May | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | High | Moderately High | | July | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | High | Moderately High | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | High | Moderately High | | September | 68.2°F (20.1°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.7°F (15.4°C) | Light Rain | Mostly Sunny | Low | Average | | November | 49.6°F (9.8°C) | Light Rain | Mostly Sunny | Low | Average | | December | 42.1°F (5.6°C) | Light Rain | Mostly Cloudy | Low | Average | ### The nearest major airports for your trip to Shelter Island To reach Shelter Island, New York, you have several airport options. Islip, NY ([ISP](https://www.expedia.ca/MacArthur-Airport-Hotels.0-aISP-0.Travel-Guide-Filter-Hotels)\-MacArthur) is situated 70.8km away, with nearby accommodations like the 3.5-star [Hyatt Regency Long Island](https://www.expedia.ca/Hauppauge-Hotels-Hyatt-Regency-Long-Island.h3668.Hotel-Information) and Jake's 58 Casino Hotel, both 6.4km from the airport, along with the [Radisson Hotel Hauppauge-Long Island](https://www.expedia.ca/Hauppauge-Hotels-Radisson-Hotel-Hauppauge-Long-Island.h10706.Hotel-Information), 14.5km away. New Haven, CT ([HVN](https://www.expedia.ca/Tweed-New-Haven-Regional-Airport-Hotels.0-aHVN-0.Travel-Guide-Filter-Hotels)\-Tweed - New Haven Regional) is 51.5km from Shelter Island, offering excellent hotels such as [The Blake Hotel](https://www.expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information), [Graduate by Hilton New Haven](https://www.expedia.ca/New-Haven-Hotels-Graduate-New-Haven.h37200005.Hotel-Information), and [Omni New Haven Hotel at Yale](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information), all 4.8km from the airport. East Hampton, NY ([HTO](https://www.expedia.ca/East-Hampton-Airport-Hotels.0-aHTO-0.Travel-Guide-Filter-Hotels)) is the closest at 14.5km away, featuring the 5-star [Mill House Inn](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) and the 4.5-star [Topping Rose House](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information), both 4.8km from the airport. ## Recent reviews of Shelter Island hotels ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 5/5 Excellent "Only issue....the refrigerator makes an annoying sound which is amlpified wearing hearing aids" A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex Posted 1 day ago [](https://expedia.ca/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 5/5 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. " A verified traveller stayed at Montauk Blue Hotel Posted 1 day ago [](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Beachcomber Resort at Montauk](//images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 5/5 Excellent "Beautiful room right across from the ocean and by town. Definitely go back!" A verified traveller stayed at Beachcomber Resort at Montauk Posted 2 days ago [](https://expedia.ca/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 5/5 Excellent "wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities" A verified traveller stayed at Gurney's Montauk Resort & Seawater Spa Posted 2 days ago [](https://expedia.ca/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 5/5 Excellent "Perfect location!" A verified traveller stayed at Sea Crest Resort Posted 2 days ago [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 5/5 Excellent "Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable and we enjoyed the breakfast which was included. " A verified traveller stayed at Quality Inn Old Saybrook - Westbrook Posted 3 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg) ### Offshore Montauk 5/5 Excellent "Super clean cut. Would be nice to have some waters in the room" A verified traveller stayed at Offshore Montauk Posted 4 days ago [](https://expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Zey Hotel](//images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978_y.jpg) ### Zey Hotel 5/5 Excellent "Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay." A verified traveller stayed at Zey Hotel Posted 4 days ago [](https://expedia.ca/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 5/5 Excellent "Beautiful grounds and quiet private beach" A verified traveller stayed at Water's Edge Resort & Spa Posted 5 days ago [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Shelter Island? > The most popular time to visit Shelter Island is during the summer months, particularly July. This is when the island truly comes alive with vibrant outdoor activities, charming events, and a bustling atmosphere. With average temperatures around 25°C, visitors can enjoy the warm weather while exploring the island's beautiful beaches, scenic walking trails, and delightful local shops. > > > > During the peak season from June to August, Shelter Island attracts a diverse crowd of travellers, making it an exciting time to experience the community vibe. You'll find plenty of opportunities for outdoor adventures, whether it's kayaking in the calm waters, cycling along the picturesque paths, or simply relaxing on the sandy shores. The long, sunlit days provide ample time for sightseeing and enjoying the island's natural beauty. > > > > For those who appreciate a quieter experience, consider visiting in September. The summer crowds begin to dwindle, yet the weather remains pleasantly warm, often still hovering around 22°C. This month also offers a wonderful opportunity to enjoy local events without the hustle and bustle of high season. You can take leisurely walks through the vineyards or indulge in fresh seafood at waterfront restaurants, all while soaking in the stunning autumnal scenery. ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island. ### How can I save on a Shelter Island hotel booking with Expedia? > Before booking your Shelter Island hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Shelter Island hotel? > Prices for hotels in Shelter Island often vary, but you can find a great deal from CA $128 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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[Visit Sag Harbor](https://www.expedia.ca/Sag-Harbor.dx154327) - [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides) - [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Car rental Orient](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide) - [Car rental Sag Harbor](https://www.expedia.ca/Car-Rentals-In-Sag-Harbor.d154327.Car-Rental-Guide) - [Sag Harbor Vacation Rentals](https://www.expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals) - [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) - [Things to do in Sag Harbor](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities) - [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities) - [Book Hotels in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on 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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