Wainscott Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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

Find the Best Wainscott Vacation Packages

Wainscott Hotel Deals

The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy Wainscott NY
The price is AEDĀ 1,466 per night from Jul 19 to Jul 20
AEDĀ 1,466
AEDĀ 1,858 total
19 Jul - 20 Jul
includes taxes & fees
8.8/10 Excellent! (276 reviews)
"Clean room, great staff, pool is nice and pet friendly."

Reviewed on 13 July 2026

The Sagaponack
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is AEDĀ 3,595 per night from Aug 9 to Aug 10
AEDĀ 3,595
AEDĀ 4,929 total
9 Aug - 10 Aug
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
The price is AEDĀ 2,286 per night from Jul 19 to Jul 20
AEDĀ 2,286
AEDĀ 3,031 total
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Lackluster staff service while somehow still being pretentious. There are better places to visit and better places to stay."

Reviewed on 13 July 2026

Montauk Yacht Club
See all 4,137 properties in Wainscott
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.

Frequently asked questions

How much does a Wainscott vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation to Wainscott costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Wainscott?
Plan your trip for the shoulder or low season and you're likely to find cheap Wainscott vacation packages. Remember that school vacation periods and local festivals and events can impact prices, so do a little research before you go.
How to find the best Wainscott package deals?
Start your search for a Wainscott package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Wainscott package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Wainscott escape underway.
Is it cheaper to book a Wainscott vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Wainscott vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Wainscott?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Wainscott escape.
How to plan a trip to Wainscott?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to visit Wainscott.
  2. Budget wisely: In addition to the price of your accommodations, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may come up during your trip to Wainscott.
  3. Decide how long to go away for: Now that you're more familiar with Wainscott, you can work out the perfect length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Wainscott vacation package.