Wainscott Vacation Rentals from $419: Search Short-Term Rentals

Q: What's the top vacation rental that Wainscott has to offer?

The Hampton Sack a cheerful relaxing beach cottage : This vacation home rental near Wainscott is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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In two weeks

In two months

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In four months

Our top choices for Wainscott vacation rentals

1. Cliffside Resort Condominiums

Greenport

Christine

$452 nightly

Aug 3 - Aug 4

Total with taxes and fees

2. North Fork Resort

Greenport

Lisa

$598 nightly

Aug 4 - Aug 5

Total with taxes and fees

Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

3. Driftwood Resort

Montauk

William

$666 nightly

Aug 31 - Sep 1

Total with taxes and fees

Iron/ironing board, WiFi (free), individually decorated

4. Windward Shores Ocean Resort

Napeague

Joseph

$595 nightly

Aug 25 - Aug 26

Total with taxes and fees

5. Montauk Manor

Montauk

Amelia

$481 nightly

Aug 17 - Aug 18

Total with taxes and fees

Apartment | Iron/ironing board, WiFi (free)

6. Montauk Oceanside Suites

Downtown Montauk

Carlos

$367 nightly

Aug 31 - Sep 1

Total with taxes and fees

7. The Surf Club

Montauk

Erica

$512 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Hamptons Vacation Rental w/ Saltwater Pool

Hampton Bays

$1,495 nightly

Aug 5 - Aug 6

Total with taxes and fees

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Top Wainscott Hotel Reviews

Montauk Manor

8/10 Good

"Nice place, lovely people. More soap and bathroom product would have been nice."

Ocean Surf Resort

8/10 Good

"The hotel was directly on the ocean and was within walking distance to the town. Room was nice, but not much room to use the small kitchenette. Beds were comfortable. Only negatives were that the air conditioner was a bit loud and lighting was poor. If given the opportunity, would rebook this hotel due to the location."

Gurney's Montauk Resort & Seawater Spa

8/10 Good

"It’s Montauk, you go here for the beach, but if you also like to dip in a pool, it’s inconvenient, plan on walking an entire trail through a parking lot to get to it. I had a prime spot for a room, choose wisely, if it’s not beachfront, you’ll also walk. It’s Gurney’s, known for its spa, it’s truly the best part of the resort, beautiful and services are fine. The staff is very nice here but SLOW. I wouldn’t say in this case you get what you pay for, if you’re looking for a Montauk vacation you’re paying for the name if you’re going for the spa you’re also paying for the spa and personally, it’s not a family vacation spot, no activities. It’s definitely a tourist spot. Dog friendly, plan to hear dogs barking."

The Bentley Hotel Southampton

8/10 Good

"We stayed here a year ago, and when we decided to drive out to the Hamptons, this was our no-brainer choice. It's not a luxury resort, but you're not gonna pay luxury prices. The "room" is truly a suite, with a large living room, which includes a kitchenette -- and a full size refrigerator, not the typical mini. The room is clean, modern and quiet. (we prefer the upper level). Our only negative is that it's really at the very start of what most people consider The Hamptons, so it's a drive -- sometimes considerable -- to get to most places."

Find out more about Wainscott

Everything you need to know about Wainscott vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wainscott vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wainscott vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wainscott vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wainscott. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wainscott in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $419 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wainscott rentals

At Expedia, we put the best Wainscott vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wainscott rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wainscott vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wainscott. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Wainscott?

Yes, we have vacation rentals near well known points of interest in Wainscott, or you can choose a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Wainscott. Make sure you have time to check out the bars and coffeehouses during your trip.

What's the top vacation rental that Wainscott has to offer?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Wainscott is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Wainscott?

Expedia has 39 vacation rentals for your stay in Wainscott.

What can I see and do in Wainscott?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like The Hamptons Beaches. In the larger area, you’ll find Georgica Beach and Wolffer Estates Vineyard.

What are vacation rentals like in Wainscott?

Vacation rentals are privately owned properties you can book for a short or long stay in Wainscott. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for small groups.

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Check prices for these dates

Our top choices for Wainscott vacation rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. Driftwood Resort

4. Windward Shores Ocean Resort

5. Montauk Manor

6. Montauk Oceanside Suites

7. The Surf Club

8. Hamptons Vacation Rental w/ Saltwater Pool

9. Offshore Spa & Residences

10. Atlantic Bluffs Club

Find vacation rentals that suit your style

Top Wainscott Hotel Reviews

Montauk Manor

Ocean Surf Resort

Zey Hotel

Gurney's Montauk Resort & Seawater Spa

Hampton's Vacation Inn

The Shoals Suites and Slips

Offshore Montauk

The Bentley Hotel Southampton

The Atlantic Hotel

Find out more about Wainscott

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