Title: Wainscott Woods Vacation Packages & Trips 2026 from CA $790 | 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)[Wainscott Woods Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott-Woods.d553248635976471516.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wainscott Woods Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Wainscott Woods Vacation When a fun city break is calling, answer it with a vacation package to Wainscott Woods. The neighborhood of Village of Southampton, which is great for history, coastal beaches and culture, makes an awesome base for your adventures. Make your trip to Wainscott Woods even more fun and exciting by including some sightseeing. [East Hampton Main Beach](https://www.expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction), [Wolffer Estates Vineyard](https://www.expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction) and [Sag Harbor Marine Park](https://www.expedia.ca/Sag-Harbor-Marine-Park-Sag-Harbor.d6327316.Vacation-Attraction) are among the top attractions you'll want to explore. Expedia will help you escape the everyday. Tailor your vacation to Wainscott Woods to suit your style of travel, whatever that may look like. ## Top Wainscott Woods Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Circle Hotel Fairfield](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/d7a51c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Circle Hotel Fairfield Grasmere CA $790 per person Apr 19 - Apr 23 found 1 day ago Roundtrip flight included Calgary (YYC) to New York (LGA) 9/10 Wonderful! (1,431 reviews) Hotel was great ! Staff was friendly and room was very clean. Bed was super comfortable but heater was so loud !!! Reviewed on Mar 17, 2026 ![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sagaponack CA $2,296 per person Jun 11 - Jun 16 found 7 hours ago Roundtrip non-stop flight included Vancouver (YVR) to New York (LGA) 8.8/10 Excellent! (228 reviews) Very charming, I stayed in one of the cottages, comfortable and well equipped. Reviewed on Mar 11, 2026 ## Ready to book your vacation to Wainscott Woods? Choose your dates ## Wainscott Woods Hotel Deals ![Private, Charming, Lovely Farmhouse in Wainscott, East Hampton ](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ba8e29ea_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Private, Charming, Lovely Farmhouse in Wainscott, East Hampton Wainscott NY CA $493 CA $1,538 total Mar 20 - Mar 21 includes taxes & fees 10/10 Exceptional! (112 reviews) Very clean rooms! Great place to stay! Great area and privacy! Host was wonderful. Would stay there again! Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=32391262&PinnedHotelID=32391262&HadPinnedHotel=true®ionId=553248635976471516) ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway Montauk NY CA $513 CA $704 total Mar 24 - Mar 25 includes taxes & fees 8.4/10 Very Good! (739 reviews) My second stay but big disappointment the pool and hot tub wasn’t available for hotel guests this is the second time for me last year same thing happened they closed the spa area there was only pool opened, our room didn’t have any coffee cups no wine glass no any other glass wear, the bathroom need ... Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true®ionId=553248635976471516) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St. Montauk NY CA $207 CA $263 total Mar 23 - Mar 24 includes taxes & fees 9.2/10 Wonderful! (1,304 reviews) Amazing! Reviewed on Mar 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=12694044&PinnedHotelID=12694044&HadPinnedHotel=true®ionId=553248635976471516) [See all 4,150 properties in Wainscott Woods](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F03%2F2026&endDate=21%2F03%2F2026®ionId=553248635976471516) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](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. Scan the QR code with your device camera and download our app