Wainscott Woods Vacation Packages

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Your Wainscott Woods Vacation

When a fun city break is calling, answer it with a vacation package to Wainscott Woods. The neighborhood of Village of Southampton, which is great for history, coastal beaches and culture, makes an awesome base for your adventures. Make your trip to Wainscott Woods even more fun and exciting by including some sightseeing. East Hampton Main Beach, Wolffer Estates Vineyard and Sag Harbor Marine Park are among the top attractions you'll want to explore. Expedia will help you escape the everyday. Tailor your vacation to Wainscott Woods to suit your style of travel, whatever that may look like.

Top Wainscott Woods Vacation Deals

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
Aug 25 - Aug 29
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to New York (LGA)
8/10 Very Good! (1,002 reviews)
Super easy and the wine bar was great!

Reviewed on Jul. 24, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
per person
Aug 25 - Aug 29
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to New York (LGA)
9/10 Wonderful! (1,377 reviews)
Love staying here. Staff is friendly -courteous and professional. I am also happy that when possible they always have the room I love available. Thank you to everyone at the circle inn my stay is always the best.

Reviewed on Jul. 24, 2025

The Sagaponack

The Sagaponack

3 out of 5
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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

Ready to book your vacation to Wainscott Woods?

 

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Wainscott Woods Hotel Deals

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is CA $724 per night from Aug 3 to Aug 4
CA $724
CA $1,084 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (189 reviews)
"Great spot on the beach and walkable to town."

Reviewed on Jul. 22, 2025

Marram
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 CA $1,181 per night from Jul 28 to Jul 29
CA $1,181
CA $1,613 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (648 reviews)
"I love it"

Reviewed on Jul. 22, 2025

Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
The price is CA $834 per night from Jul 27 to Jul 28
CA $834
CA $1,108 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"I have come here for a while and is the best place to stay in mtk. A little outside of the main areas but you can’t beat the pool."

Reviewed on Jul. 24, 2025

Montauk Yacht Club
See all 4,160 properties in Wainscott Woods
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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Wainscott Woods vacation package cost?
You'll find cheap prices from CA $673 on Expedia for your Wainscott Woods getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Wainscott Woods costs.
What are the cheapest months to go to Wainscott Woods?
To pick up cheap Wainscott Woods vacation packages, plan your trip outside of peak times like public holidays and major events. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Wainscott Woods?
Generally, a handful of days is enough to go to the main attractions during your Wainscott Woods vacation. However, if you prefer to have some time to relax or go on day trips, think about extending your trip.
How to find the best Wainscott Woods package deals?
Start your search for a Wainscott Woods package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Wainscott Woods package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wainscott Woods escape underway.
Is it cheaper to book a Wainscott Woods vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Wainscott Woods vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Wainscott Woods?
If you're planning an impromptu Wainscott Woods vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Wainscott Woods?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite season and the type of activities available will also help you decide when to escape to Wainscott Woods.
  2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Wainscott Woods. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Decide how long to go for: Now that you're up to speed on Wainscott Woods, you can figure out the ideal length of your vacation. Put together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Wainscott Woods vacation package.

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