Wainscott Vacation Packages 2026 from $405

Wainscott flight + hotel vacation packages

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

The Sagaponack

$405

per person

Mar 16 - Mar 17

found 2 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to New York (LGA)

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A communal living room and luggage storage are also provided.

Wainscott Woods Retreat

$425

per person

Mar 16 - Mar 17

found 2 hours ago

Roundtrip non-stop flight included

Las Vegas (LAS) to New York (LGA)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Top Wainscott hotels deals

The Sagaponack

3720 Montauk Hwy Wainscott NY

$184 nightly

$211 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A communal living room and luggage storage are also provided.

Pool

Pet friendly

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$418 nightly

$478 total

Jan 25 - Jan 26, 2026

Total with taxes and fees

This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

On private beach

Pool

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

Get rates

This hotel features an indoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.

Pool

Hot Tub

Offshore Montauk

71 S Emerson Ave Montauk NY

$166 nightly

$190 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.

Pool

Pet friendly

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$144 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a garden and multilingual staff can provide around-the-clock assistance.

Pool

Pet friendly

Montauk Manor

236 Edgemere St. Montauk NY

$156 nightly

$178 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

3 outdoor tennis courts, an indoor pool, and a 24-hour gym are all featured at this smoke-free aparthotel. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a restaurant and a bar/lounge for dining and drinks, and also a hot tub on site.

Pool

Hot Tub

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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.

Frequently asked questions

How much are vacation packages to Wainscott?

Travelocity provides package deals to Wainscott, including flights and hotels, starting at just $405. With the cash you save, you could book some cool tours or possibly even add a couple of extra days to your exciting adventure.

Where can I get the best vacation package deals for Wainscott?

Walking away with a great package deal to Wainscott couldn't be easier with Travelocity. With 400 airlines and 1,000,000 worldwide properties, you'll have loads of choice when it comes to picking your hotels and flights.

Why should I book my Wainscott vacation bundle via Travelocity?

Because we believe in creating one-of-a-kind travel experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our customer care is available 24/7 to ensure you'll never roam alone. We also offer a Price Match Guarantee, so you can lock in your trip knowing you've landed the best deal possible. If you find a lower price, we'll match it!

Will I save money on my Wainscott car rental if I bundle it with my hotel or flight?

Certainly. And our Wainscott vacation packages are the best way to do it. In only a few clicks you can save cash as well as time by combining your bookings. Pick up the keys to your rental car and do your vacation your way. Need to fill your itinerary? Add a few tours to your package and make savings on those too.