Wainscott Vacations from $333

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 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.

The Latest Wainscott vacation packages

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $511, price is now $333 per person
$333
per person
Apr 24 - Apr 27
found 4 hours ago
Roundtrip flight included
Charlotte (CLT) to New York (LGA)
7.8/10 Good! (80 reviews)
Room was clean, super quiet, staff was very helpful and nice

Reviewed on Feb 15, 2026

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2 out of 5
Save 100% on your flight
Price was $1,715, price is now $1,486 per person
$1,486
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (LGA)
No reviews
Honey Maple Grove BnB

Honey Maple Grove BnB

4 out of 5
Price was $543, price is now $528 per person
$528
per person
May 14 - May 16
found 9 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
8.4/10 Very Good! (7 reviews)
We had a lovely experience. I particularly enjoyed the community breakfast table. The other guest were wonderful as were the conversations (hosts included).

Reviewed on Oct 28, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Grasmere
Price was $837, price is now $751 per person
$751
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
9/10 Wonderful! (1,401 reviews)
Great place to stay.

Reviewed on Feb 15, 2026

Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Greenfield Hill
Price was $802, price is now $728 per person
$728
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
8/10 Very Good! (1,001 reviews)
Easy check. Great location, right off of the high way and close to SHU.

Reviewed on Feb 11, 2026

Don't see what you're looking for?
See all available trips from Columbus to Wainscott
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Wainscott Hotel Deals

The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy Wainscott NY
$196 nightly
The price is $220 total per night from Feb 19 to Feb 20
$220 total
Feb 19 - Feb 20
Total with taxes and fees
8.8/10 Excellent! (224 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

The Sagaponack
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$344 nightly
The price is $393 total per night from Feb 22 to Feb 23
$393 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (728 reviews)
The room Was ready early and spotless The stuffy lobsters for the girls was a nice touch

Reviewed on Feb 16, 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$164 nightly
The price is $187 total per night from Mar 19 to Mar 20
$187 total
Mar 19 - Mar 20
Total with taxes and fees
8.4/10 Very Good! (613 reviews)
Hotel complaints Extra unknown/ non-disclosed charges- 13 arrival and 15 checkout **there are more charges than shown in Expedia Rooms not matching pictures (told to have an ocean view when not the case) Some ice on road/ sidewalk (seen someone slip) Disappointing “continental” breakfast Parking ...

Reviewed on Feb 15, 2026

Sound View Greenport
See all 4,145 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.

Find the Best Wainscott Vacation Packages

Wainscott Essential Information

Language
English
Currency
U.S dollars
Population
650
Max Temp Winter
40ºF
Max Temp Summer
75ºF
Top Sights
Coopers Beach, Wolffer Estates Vineyard and East Hampton Main Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Wainscott vacation package cost?
You can snap up a vacation package to this popular destination from $333 on Expedia. But how much your vacation to Wainscott costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Wainscott?
If you'd like to snag a cheap Wainscott vacation package, consider traveling in January, October and December. You're likely to find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Wainscott?
Typically, a handful of days is enough to see the main attractions during your Wainscott vacation. However, if you'd like to have more time to chill out or go on day trips, think about extending your itinerary.
How to find the best Wainscott package deals?
Use Expedia's filter tool to help you find some terrific Wainscott package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Wainscott package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Wainscott vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can customize your Wainscott getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Wainscott?
If you have your Wainscott vacation dates confirmed, book early to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Wainscott?

  1. Pick your travel dates: What you plan to do in Wainscott and your favorite season will help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Wainscott.
  3. Discover Wainscott using our trip planning tool: Gain insights into the leading attractions and best stays for your trip to Wainscott. You can also save your favorite places, collaborate with family and friends and organize your plans in one place.
  4. Determine how many days away: Start by listing all the attractions and activities you want to experience in Wainscott. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Wainscott vacation package.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Wainscott's best offerings. Find all the fun things to do in Wainscott in Wainscott with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Wainscott vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Wainscott break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.

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.