Wainscott Vacations from $442

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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.
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
per person
Sep 4 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (LGA)
8/10 Very Good! (1,002 reviews)
It was clean but very small. I didn’t like bo staff on property if something was wrong or went wrong. Definitely needs a mini fridge in rooms but it was perfect for a quick one day stay

Reviewed on Jul 5, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
per person
Oct 4 - Oct 10
found 3 hours ago
Roundtrip flight included
Denver (DEN) to New York (LGA)
9/10 Wonderful! (1,377 reviews)
Love it but the area is a little expensive

Reviewed on Jul 11, 2025

The Sagaponack

The Sagaponack

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 21
found 6 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (LGA)
8.8/10 Excellent! (157 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 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to New York (LGA)
9/10 Wonderful! (55 reviews)
Incredible staff, friendly, helpful.

Reviewed on Jun 29, 2025

Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
per person
Sep 4 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (LGA)
8/10 Very Good! (1,003 reviews)
Room was great, bed super comfortable. Very small parking lot

Reviewed on Jul 9, 2025

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Wainscott Hotel Deals

The Sagaponack
The Sagaponack
3 out of 5
3720 Montauk Hwy, Wainscott, NY
$445 nightly
The price is $508 total per night from Jul 13 to Jul 14
$508 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (161 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
$1,942 nightly
The price is $2,219 total per night from Jul 20 to Jul 21
$2,219 total
Jul 20 - Jul 21
Total includes taxes and 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
$689 nightly
The price is $787 total per night from Jul 16 to Jul 17
$787 total
Jul 16 - Jul 17
Total includes taxes and fees
8.6/10 Excellent! (178 reviews)
Marrom hotel stay
"Javier ( manager), Luisa (pool attendant) and staff were exceptional!!!! The accommodation and considerations were so great. We only stayed one night but aren’t leaving without booking another trip soon. Btw, the food for adults were fantastic, however nothing to accommodate the kids which was weird ..."

Reviewed on Jul 9, 2025

Marram
See all 4,224 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 $442 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.