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Dec 22 - Dec 26
Montauk
4 nights
9.2/10 - Wonderful (235 reviews)
"Great stay at Offshore Hotel in Montauk. The king bed and pillows were most comfy! Edwardo got us beach chairs and we grabbed a bottle of wine to watch a perfect sunset, oceanside in November! Very close to restaurants and shopping. The sauna and red light therapy rooms in the wellness center a were a nice touch. Great spot for a 2 night getaway."
Reviewed November 13, 2026
Roundtrip • Toronto (YTO) - New York (JFK)
YYZ - EWR • Nonstop LGA - YYZ • Nonstop
CA $1,126
per traveller
found 1 day ago
Dec 22 - Dec 26
Sag Harbor
4 nights
9.0/10 - Wonderful (322 reviews)
"One of my favorite hotels! Every detail was immaculate."
Reviewed November 13, 2026
Roundtrip • Toronto (YTO) - New York (JFK)
YYZ - EWR • Nonstop LGA - YYZ • Nonstop
CA $1,303
per traveller
found 1 day ago
Rating: 9.6/10 (735 reviews)
Check out hiking trails, fishing spots, surf beaches and historic landmarks at the expansive nature reserve on the eastern tip of Long Island’s South Fork.
Rating: 9.2/10 (784 reviews)
Learn about New York State’s oldest lighthouse in its museum before climbing to the top for panoramic ocean views.
Rating: 9.2/10 (171 reviews)
Escape NYC to play in the waves, sunbathe on fine, white sands or stroll past the exclusive mansions that line the dunes of one of the best beaches in the Hamptons.
Rating: 9.2/10 (146 reviews)
On the eastern edge of Long Island, enjoy a day on this exclusive beach complete with lifeguards, restrooms, a snack bar and other amenities.
Rating: 9.2/10 (187 reviews)
Commune with nature and explore the great outdoors at Lake Montauk during your travels in Montauk. Wander the beautiful beaches and seaside in the area.
Rating: 9.4/10 (83 reviews)
Discover the country charm of the Hamptons by visiting this European-style winery with nearby equestrian center, outdoor wine bar and classy restaurants.
Rating: 9.2/10 (205 reviews)
Go fishing, hiking, biking or cross-country skiing at this coastal nature reserve and stay overnight at the park’s scenic waterfront campgrounds.
Rating: 8.6/10 (14 reviews)
Enjoy a round of golf in Tuckahoe at Shinnecock Hills Golf Course. While you're in the area, stroll along the beautiful beaches.
CA $267
per adult
0% of travellers recommend
CA $1,837
per traveller
100% of travellers recommend
CA $1,833
per traveller
0% of travellers recommend
See all activities in Hamptons
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.
See all properties in Hamptons
We make it easy to explore the world, with Hamptons packages starting from as low as CA $1,126. You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate escape, why not add a couple of experiences and tours to your itinerary?
If you love scoring a bargain, combine your bookings into a Hamptons vacation package. Whether you need hotels, flights, rental cars or activities, you can book them all in one place. You'll have a wealth of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options all over the world to take your pick of. Fly with who you want, stay in a place you like and save some cash — now that's the perfect getaway!
Southampton Inn and The Atlantic Hotel are some excellent options in the Village of Southampton neighborhood. If you're thinking of staying in the East Hampton North area, we recommend booking a few nights at The 1770 House Restaurant And Inn or The Huntting Inn.
It depends on the air carrier, but you can normally browse through international airfares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky customers will occasionally nab a cheaper flight just weeks before their intended journey.
Hotels, flights and rental cars, or any combination of them — the choice is yours. Whether you're headed to Hamptons with the kids or traveling with your friends, there's a package to fit every style and budget. Once you've made your booking, why not add on a few activities?
Get ready to save with an Expedia travel package. Combine your flights, rental cars and hotels and score great discounts. Hotels aren't your only option, though. We have beach villas, creek-side mountain cabins and even treehouses and ranches!
Expedia offers access to more than 550 airline partners globally, so you sure can! Just choose your favorite carrier and put together your ideal Hamptons getaway.
Whether it's your hotel, flight or rental car, you can cancel or change it. Booked your Hamptons vacation package in the last 24 hours? You may be able to make changes for free. For older bookings, you may incur a charge from your hotel, airline or car rental company. For further information, visit our Customer Service Portal. We'll help you every step of the way.