Title: 5 Stars Hotels in Wainscott Woods, Wainscott from CA $456 - Find Cheap Wainscott Woods Hotels With 5 Stars | Expedia.ca [Wainscott Woods Travel Guide](https://expedia.ca/Wainscott-Woods.dx553248635976471516)[Hotels in Wainscott Woods](https://expedia.ca/Wainscott-Woods-Hotels.d553248635976471516.Travel-Guide-Hotels)[Vacation Rentals in Wainscott Woods](https://expedia.ca/Wainscott-Woods-Vacation-Rentals.d553248635976471516.Travel-Guide-VacationRentals)[Flights to Wainscott Woods](https://expedia.ca/Cheap-Flights-To-Wainscott-Woods.d553248635976471516.Travel-Guide-Flights)[Wainscott Woods Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott-Woods.d553248635976471516.Car-Rental-Guide)[Wainscott Woods Vacation Packages](https://expedia.ca/Wainscott-Woods.d553248635976471516.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/f54a09d2ea13aa6d589bee6eb9eaff7c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Miriam Marcus # 5 Stars Hotels in Wainscott Woods, Wainscott from CA $456 ![](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 availability on Wainscott Woods 5 Star Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wainscott Woods 5 Star Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn North Main Street Historic District 9.0/10 Wonderful (70) "Great experience at a wonderful property!" CA $455 CA $572 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![House | Outdoor pool](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/23f4590c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/a4e472c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Staircase](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/96fc375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Front of property](https://images.trvl-media.com/lodging/33000000/32420000/32411100/32411044/61df3ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Newmark Holiday home 7 BestStayz.1 Sagaponack [](https://www.expedia.ca/Sagaponack-Hotels-Casa-Newmark-Holiday-Home-7-BestStayz1.h32411044.Hotel-Information) ![](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%2F5Star-Wainscott-Woods-Hotels.s50-0-d553248635976471516.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Wainscott-Woods-Hotels.s50-0-d553248635976471516.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Wainscott Woods. ![Montauk Yacht Club](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Montauk Yacht Club 32 Star Island Rd, Montauk, NY CA $261 CA $458 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (1,002 reviews) [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sound View Greenport 58775 County Rd 48, Greenport, NY CA $339 CA $456 total Oct 21 - Oct 22 includes taxes & fees 8.4/10 Very Good! (577 reviews) [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway, Montauk, NY CA $379 CA $518 total Nov 13 - Nov 14 includes taxes & fees 8.2/10 Very Good! (669 reviews) [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) Still don't see what you're looking for? [See all properties in Wainscott Woods.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976471516&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Wainscott Woods Check out Wolffer Estates Vineyard and Georgica Beach—just a couple of the sights around Wainscott Woods. [See all hotels in Wainscott Woods](https://www.expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&adults=2®ionId=553248635976471516) ![](https://mediaim.expedia.com/destination/2/f54a09d2ea13aa6d589bee6eb9eaff7c.jpg?impolicy=fcrop&w=655&h=655&p=1&q=high) Photo by Miriam Marcus ## Top Wainscott Woods Hotel Reviews ## Find out more about Wainscott Woods Luxury is the name of the game at the best 5 Stars hotels in Wainscott Woods. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Wainscott Woods 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Wainscott Woods hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Wainscott Woods without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Wainscott Woods. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Hamptons](https://www.expedia.ca/1Star-Hamptons-Hotels.s10-0-d6056452.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Plandome Heights](https://www.expedia.ca/1Star-Plandome-Heights-Hotels.s10-0-d553248634998735582.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Lido Beach](https://www.expedia.ca/2Star-Lido-Beach-Hotels.s20-0-d6287455.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Lindenhurst](https://www.expedia.ca/2Star-Lindenhurst-Hotels.s20-0-d183693.Travel-Guide-Filter-Hotels) - [2 Star Hotels in North New Hyde Park](https://www.expedia.ca/2Star-North-New-Hyde-Park-New-Hyde-Park-Hotels.s20-n553248634999001045-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Wheatley Heights](https://www.expedia.ca/2Star-Wheatley-Heights-Hotels.s20-0-d3000450118.Travel-Guide-Filter-Hotels) - 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