Wainscott Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
per person
Oct 3 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (LGA)
9/10 Wonderful! (1,377 reviews)
Cozy quiet clean rooms with friendly professional staff

Reviewed on Jul. 31, 2025

Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (LGA)
8/10 Very Good! (1,002 reviews)
Great if you like not being able to check in because your phone has the wrong browser and fire alarms from steamy showers 3 time in 2 days. Wow

Reviewed on Jul. 27, 2025

The Sagaponack

The Sagaponack

3 out of 5
per person
Sep 2 - Sep 9
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to New York (LGA)
8.8/10 Excellent! (161 reviews)
Great experience. Comfortable beds pool was heated to the perfect temperature. Overall atmosphere is great.

Reviewed on Jul. 5, 2025

DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (LGA)
9/10 Wonderful! (59 reviews)
Incredible staff, friendly, helpful.

Reviewed on Jun. 29, 2025

Ready to book your vacation to Wainscott?

 

Choose your dates

Wainscott Hotel Deals

The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy, Wainscott, NY
The price is CA $472 per night from Sep 1 to Sep 2
CA $472
CA $595 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (164 reviews)
"It was good"

Reviewed on Jul. 6, 2025

The Sagaponack
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Wainscott
The price is CA $1,248 per night from Sep 1 to Sep 2
CA $1,248
CA $2,483 total
Sep 1 - Sep 2
includes taxes & fees
Beautiful!
"We had an excellent stay and the host was super communicative and helpful! Can’t wait to come back again! Thank you!"

Reviewed on Aug. 31, 2024

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is CA $588 per night from Sep 1 to Sep 2
CA $588
CA $933 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (192 reviews)
"We really enjoyed our stay at Marram and would return in the future. The beach is beautiful and they have more than enough chairs and umbrellas to go around. Staff was friendly and helpful and the property was very well maintained. The location is great and easily walkable to most areas. They have ..."

Reviewed on Jul. 28, 2025

Marram
See all 4,185 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Wainscott vacation package cost?
You can snap up a vacation package to this popular destination from CA $821 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 many days is enough for Wainscott?
With around 2 days, you'll have plenty of time to experience popular neighbourhoods like East Hampton North and Wainscott Woods during your Wainscott vacation. Make sure to also add Bay Street Theatre and LongHouse Reserve to your sightseeing itinerary. Up for some more adventures? Consider exploring outside of Wainscott on tours and day trips.
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 favourite 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 favourite 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.