Title: Wainscott Chalets from CA $159 | Expedia.ca [Hotels in Wainscott](https://expedia.ca/Wainscott-Hotels.d6046784.Travel-Guide-Hotels)[Vacation Rentals in Wainscott](https://expedia.ca/Wainscott-Vacation-Rentals.d6046784.Travel-Guide-VacationRentals)[Wainscott Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott.d6046784.Car-Rental-Guide)[Wainscott Vacation Packages](https://expedia.ca/Wainscott.d6046784.Destination-Travel-Guides) ![Amerikanischer Strand auf Long Island bei New York](https://images.trvl-media.com/place/6046784/20a21c13-09f9-4231-8e0a-98fb1f8c34ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Wainscott from CA $159 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Wainscott ![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/2f7aacee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/5c1700b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) Wainscott 8.8/10 Excellent (211) "Clean & amenities, staff friendly Thank you " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Archil CA $196 CA $280 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/7bd037b9.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/33000000/32400000/32391300/32391262/2b5114d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/74678c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ba8e29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, Charming, Lovely Farmhouse in Wainscott, East Hampton [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) Wainscott 10/10 Exceptional (112) "We had a great stay at the house - it's perfect for a family and the kids love the pool ! Would definitely stay again and perfect for long term rental as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy P. CA $997 CA $2,196 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/280d0e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/f417f407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/a2d322f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Studio Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/e9280c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wainscott Woods Retreat [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information) Wainscott 7.0/10 Good (9) "Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivan CA $312 CA $357 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w907h683x59y0-59a3d8e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-6196bd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w906h683x58y0-bc7fef2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119900000/119891500/119891409/w905h683x60y0-eb7cd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 5 Bedroom With Wi-fi And Air Condition [](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) Wainscott CA $2,069 CA $2,688 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Wainscott-Hotels-Cozy-5-Bedroom-With-Wi-Fi-And-Air-Condition.h119891409.Hotel-Information) ![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/7a155d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![El Presidente | View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/0404b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Offshore Montauk [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) Montauk 9.2/10 Wonderful (77) "Nice decoration, clean amenities, good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) weihao CA $161 CA $263 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/11d8806e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/c263e1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/302ae081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (440) "Great weekend stay! staff was super kind and property was beautiful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyanne CA $123 CA $159 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/334e85c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/6222b412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (392) "great cost-effective option; room was very spacious and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isadora CA $158 CA $182 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/176892a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/dc79a27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/89358591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) Culloden Shores 8.4/10 Very good (878) "Really clean and nice location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiara CA $160 CA $190 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![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) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.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.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) Montauk 9.2/10 Wonderful (1265) "Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Violet CA $192 CA $246 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/c4264a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Bay View | Room amenity](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/e54c439c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/07ec8098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House on Chase Creek [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information) The Heights 9.4/10 Exceptional (79) " This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $144 CA $165 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/7ebc6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (544) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $182 CA $275 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/147e40ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/1bb00541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shorewood Inn [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) Riverhead 8.4/10 Very good (708) "Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mahlon [](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/90ac61e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King | Living area](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/582203a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace King](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/efe41897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/7f5c2322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shoals Suites and Slips [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) Southold 9.6/10 Exceptional (227) "Food!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $241 CA $276 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/0a5356ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze #3: Cozy Cottage by the beach [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) Hampton Bays 10/10 Exceptional (1) CA $76 CA $633 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/d63abefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/6f482e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/ea7d9e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/f1b58415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daunt's Albatross Motel [](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information) Downtown Montauk 9.0/10 Wonderful (288) "The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany [](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information) ![Suite | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/784055fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/f1ebef28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/2fdf39bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/22da4a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hero Beach Club [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) Montauk 9.0/10 Wonderful (202) "Great weekend trip " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $198 CA $367 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/43997189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/a7c5a78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (598) "Staff was amazing , room clean view phenomenal " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $242 CA $345 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/9091cefd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/65a6ec82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/d9d8edde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Beech Hotel [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) Greenport 8.8/10 Excellent (195) "The property was clean beautiful and pleasant. Loved the trendy decor." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $276 CA $370 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/2bfbb5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Living area](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/0fc29bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/885537fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/w3438h2272x6y0-ee61100c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southampton Long Island Hotel [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) Southampton 8.6/10 Excellent (203) "Good location. Nice people!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $164 CA $196 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information) ![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/dde88cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/8e47f99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/d1fe07eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) Pantigo Road Historic District 9.0/10 Wonderful (73) "We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) margaret CA $415 CA $522 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.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=2025-12-24&endDate=2025-12-25®ionId=6046784&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWainscott-Chalets.d6046784-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWainscott-Chalets.d6046784-aaChalets.Travel-Guide-Accommodation) ## Top Wainscott Hotel Reviews ![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg) ### The Shoals Suites and Slips 10/10 Excellent "Great sta" [](https://expedia.ca/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay." [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg) ### The Bentley Hotel Southampton 10/10 Excellent "Had a wonderful stay at The Bentley Hotel Southampton. The room was spacious, stylish, and spotless. I especially loved the record player — such a unique and thoughtful touch that made the stay feel personal and relaxing. The overall vibe of the room and the layout were perfect. Staff were friendly and the property felt well cared for. I’d definitely stay here again and highly recommend it." [](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg) ### The Harbor Front Inn 10/10 Excellent "Monica really helped us out with our last-minute travel needs. She's a gem and so is this Inn and the North Fork in general. We'll be back." [](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg) ### Sag Harbor Inn 10/10 Excellent "Very clean, helpful staff and convenient location." [](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg) ### The Sagaponack 10/10 Excellent "Everything was amazing! Friendly service! " [](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg) ### Montauk Manor 10/10 Excellent "Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. " [](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Great room with amazing views! Staff was fantastic and the food was great too" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great hotel for a quick stay - very friendly staff" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ## Find out more about Wainscott ## Wainscott Chalets information | Number of reviews | 6,418 | | ----------------- | --------- | | Accommodation | 1 Chalets | | Lowest Price | CA $159 | | Highest Price | CA $2,688 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Bridgehampton ](https://www.expedia.ca/Bridgehampton-Bed-And-Breakfast.d6130684-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Bridgehampton ](https://www.expedia.ca/Bridgehampton-Hotels-Beach-Hotel.0-0-d6130684-tBeachHotel.Travel-Guide-Filter-Hotels) - 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