Wainscott Vacation Packages
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Your Wainscott Vacation
Book a Wainscott vacation package that includes only the things you need and nothing you don't. Good for history, coastal beaches and culture, think about staying in the neighborhood of Village of Southampton. East Hampton Main Beach, Wolffer Estates Vineyard and Sag Harbor Marine Park are just a few of the sights worth visiting during your trip to Wainscott. That dream Wainscott vacation is a couple of clicks away. Search hotels, flights and more on Expedia for a getaway that's tailored to suit your style.
Top Wainscott Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson
Price was CA $1,003, price is now CA $765 per person
CA $765
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (LGA)
7.8/10 Good! (80 reviews)
The rooms need more amenities such as a coffee maker some cups and utensils, as well as a guide to the television set.
Reviewed on Dec 28, 2025
Wainscott Hotel Deals
The Sagaponack
3720 Montauk Hwy Wainscott NY
The price is CA $198 per night from Mar 9 to Mar 10
CA $198
CA $282 total
Mar 9 - Mar 10
includes taxes & fees
8.6/10 Excellent! (223 reviews)
The staff was wonderful. We stayed in the hotel suite which was a great side for two adults and two kids. Everything was very nicely upkept. It's a great location in the middle of many things to do, short drive away from the main town. My only complaint would be a bit of the street traffic noise ...
Reviewed on Jan 21, 2026
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Wainscott NY
The price is CA $985 per night from Feb 9 to Feb 10
CA $985
CA $2,173 total
Feb 9 - Feb 10
includes taxes & fees
9.8/10 Exceptional! (38 reviews)
Very clean rooms! Great place to stay! Great area and privacy! Host was wonderful. Would stay there again!
Reviewed on Sep 27, 2025
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is CA $427 per night from Feb 22 to Feb 23
CA $427
CA $586 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (722 reviews)
Room was spotless, staff were great and the resort is top notch!!
Reviewed on Feb 2, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
