Title: Adventure Vacations in Hamptons 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635695603591/4fa59c19-0bff-4c13-9d62-705359d33679.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Hamptons Adventure Vacations ## 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 ## Flight and Adventure hotel deals in Hamptons Price found within the past 48 hours. Click for updated prices. ![The Maidstone](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/99260f7f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Maidstone CA $2,206 per person Jan 11 - Jan 18 found 13 hours ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 8/10 Very Good! (150 reviews) We had a wonderful stay Reviewed on Sep 9, 2025 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House CA $3,215 per person Jan 11 - Jan 18 found 13 hours ago Roundtrip flight included Toronto (YYZ) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 Don't see what you're looking for? See all available trips from Columbus to Hamptons [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=LGA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Adventure Hotels in Hamptons ![Montauk Yacht Club](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Yacht Club 32 Star Island Rd Montauk NY - 12 min drive from Montauk Point Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ... 8.6/10 Excellent! (1,002 reviews) Amazing property! Excellent service Reviewed on Nov 27, 2025 [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![434 on Main](https://images.trvl-media.com/lodging/13000000/12780000/12779400/12779331/59df497c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 434 on Main 434 Main Street Amagansett NY - 48 min drive from Montauk Point Stay at this B&B in Amagansett. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Amagansett Square and Amelia Cottage Museum are located ... 9.8/10 Exceptional! (36 reviews) Nice property in an area that is crazy expensive. The hosts are warm and wonderful. We were there on a cold rainy summer weekend, and I was uncomfortable with the cold air that was fan-fed through vents throughout the house. Also had minor problems with the television in our room, and the darkness ... Reviewed on Jul 16, 2025 [](https://expedia.ca/Amagansett-Hotels-434-On-Main.h12779331.Hotel-Information) ![Bayview Resort](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bayview Resort 53 West Tiana Road Hampton Bays NY - 2 hours drive from Montauk Point Book a stay at this beach motel in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ... 8.6/10 Excellent! (455 reviews) Just right. Reviewed on Nov 19, 2025 [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) [See all 3,667 properties in Hamptons](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6056452) 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. ## More vacations you might like ![](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) ## More Vacations Ideas [Flights to Hamptons ](https://expedia.ca/Cheap-Flights-To-Hamptons.d6056452.Travel-Guide-Flights)[ Hamptons Hotels ](https://expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)[ Hamptons Vacation Rentals ](https://expedia.ca/Hamptons-Vacation-Rentals.d6056452.Travel-Guide-VacationRentals)[ Hamptons Car Rentals ](https://expedia.ca/Car-Rentals-In-Hamptons.d6056452.Car-Rental-Guide)[ Hamptons Vacations ](https://expedia.ca/Hamptons.d6056452.Destination-Travel-Guides)[ Things to do in Hamptons ](https://expedia.ca/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities) \* 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