Wainscott Vacations from $336

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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.

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 $501, price is now $336 per person
$336
per person
Feb 27 - Mar 2
found 2 days ago
Roundtrip flight included
Dallas (DFW) 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

The Sagaponack

The Sagaponack

3 out of 5
Save 100% on your flight
Price was $1,062, price is now $882 per person
$882
per person
Mar 6 - Mar 13
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to New York (LGA)
8.8/10 Excellent! (205 reviews)
The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!

Reviewed on Jan 3, 2026

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Grasmere
Price was $718, price is now $626 per person
$626
per person
Feb 23 - Feb 27
found 11 hours ago
Roundtrip non-stop flight included
Miami (MIA) to New York (LGA)
9/10 Wonderful! (1,401 reviews)
Room was great! The bed and couch was amazing! Coming again soon

Reviewed on Jan 18, 2026

Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
Greenfield Hill
Price was $475, price is now $430 per person
$430
per person
Mar 6 - Mar 8
found 15 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (LGA)
8/10 Very Good! (1,001 reviews)
The room was clean and comfortable. There is no refridgerator

Reviewed on Jan 20, 2026

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Wainscott Hotel Deals

The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy Wainscott NY
$196 nightly
The price is $224 total per night from Jan 23 to Jan 24
$224 total
Jan 23 - Jan 24
Total with taxes and fees
8.6/10 Excellent! (221 reviews)
beach bonfire on my tv upon welcome was such a nice touch! thank you :) 9/10!! towels had a slight odor (maybe just left in the washer too long) and there were a few hairs on the shower wall when i went to use it for the first time. otherwise room was gorgeous and really pretty grounds. super easy ...

Reviewed on Jan 5, 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
$316 nightly
The price is $361 total per night from Feb 9 to Feb 10
$361 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (719 reviews)
Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !

Reviewed on Jan 12, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
9.2/10 Wonderful! (187 reviews)
I always have a 5/5 stay at Montauk Blue.

Reviewed on Nov 19, 2025

Get rates
Montauk Blue Hotel
See all 4,118 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

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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 $336 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.

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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.