Title: Cutchogue Vacation Packages & Trips 2026 from CA $862 | Expedia.ca [Hotels in Cutchogue](https://expedia.ca/Cutchogue-Hotels.d183659.Travel-Guide-Hotels)[Vacation Rentals in Cutchogue](https://expedia.ca/Cutchogue-Vacation-Rentals.d183659.Travel-Guide-VacationRentals)[Cutchogue Car Rentals](https://expedia.ca/Car-Rentals-In-Cutchogue.d183659.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183659/5b925f81-ea4b-4e7a-b93a-66611b53a810.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cutchogue 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 Cutchogue Vacation With plenty of highlights as well as some hidden gems, this city is best explored with a Cutchogue vacation package. Find a place to stay in Village of Southampton, which is good for history, coastal beaches and culture. If taking in sights is part of the plan during your trip to Cutchogue, swing by leading attractions like [Macari Vineyards](https://www.expedia.ca/Macari-Vineyards-Mattituck.d6326944.Vacation-Attraction), [Raphael Winery](https://www.expedia.ca/Raphael-Winery-Peconic.d6327146.Vacation-Attraction) and [Pindar Vineyards](https://www.expedia.ca/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction). That dream Cutchogue vacation is just a few clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored just for you. ## Top Cutchogue Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $862 per person Mar 12 - Mar 15 found 13 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $3,029 per person Apr 16 - Apr 21 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) You need more dinner options in hotel Reviewed on Jan 17, 2026 ![Lotte New York Palace](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1695h1110x0y0-027534be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lotte New York Palace Manhattan CA $1,818 per person Mar 18 - Mar 23 found 13 hours ago Roundtrip non-stop flight included Edmonton (YEG) to New York (JFK) 9/10 Wonderful! (1,723 reviews) Everything was excellent!! Reviewed on Jan 23, 2026 ![Park Lane New York](https://images.trvl-media.com/lodging/1000000/10000/2800/2714/50f6b46d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Lane New York Manhattan CA $1,689 per person Mar 15 - Mar 21 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.4/10 Very Good! (1,667 reviews) Nice hotel with very good location Reviewed on Jan 23, 2026 ## Ready to book your vacation to Cutchogue? Choose your dates ## Cutchogue Hotel Deals ![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier Blue Inn Old Saybrook - Essex 1430 Boston Post Rd Old Saybrook CT Fully refundableReserve now, pay when you stay CA $97 CA $112 total Jan 26 - Jan 27 includes taxes & fees 7.8/10 Good! (1,001 reviews) muy limpias Reviewed on Jan 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true®ionId=183659) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sound View Greenport 58775 County Rd 48 Greenport NY CA $184 CA $249 total Feb 2 - Feb 3 includes taxes & fees 8.4/10 Very Good! (607 reviews) This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ... Reviewed on Jan 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true®ionId=183659) ![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Riverhead 2038 Old Country Rd Riverhead NY Fully refundableReserve now, pay when you stay CA $152 CA $173 total Feb 1 - Feb 2 includes taxes & fees 8.4/10 Very Good! (1,001 reviews) Excellent service Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=1962521&PinnedHotelID=1962521&HadPinnedHotel=true®ionId=183659) [See all 4,266 properties in Cutchogue](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F01%2F2026&endDate=26%2F01%2F2026®ionId=183659) 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) ### Discover the most popular places to visit in Cutchogue ![Wine on the vine!](https://images.trvl-media.com/place/144477/097a28ec-b48b-4a02-aef3-3c165612407a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bedell Cellars You can enjoy a tasting or tour at Bedell Cellars during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches. [](https://expedia.ca/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction) ### What to do in Cutchogue ![East Hampton Shops](https://mediaim.expedia.com/localexpert/691732/ee4533c8-13fa-4c8f-94a4-df282ec83489.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Hamptons Private Day Trip from New York City CA $1,804 per traveller [](https://expedia.ca/things-to-do/hamptons-private-day-trip-from-new-york-city.a691732.activity-details) ![Wine and grapes against the sea](https://mediaim.expedia.com/localexpert/1381172/1aab586f-aafa-4638-b216-8c88ceec22f3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### The Hamptons and Long Island Wineries Private Tour CA $1,804 per traveller [](https://expedia.ca/things-to-do/the-hamptons-and-long-island-wineries-private-tour.a1381172.activity-details) [See all activities in Cutchogue](https://expedia.ca/things-to-do/search?rid=183659) ## 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