Wainscott Woods Vacation Rentals from ₩345,554: Search Short-Term Rentals

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Our top choices for Wainscott Woods vacation rentals

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

1. Windward Shores Ocean Resort

Napeague

Gaurang J

₩429,206 total

includes taxes & fees

Sep 14 - Sep 15

2. Cliffside Resort Condominiums

Greenport

Christine

₩621,936 total

includes taxes & fees

Sep 7 - Sep 8

3. Montauk Manor

Montauk

Amelia

₩508,088 total

includes taxes & fees

Sep 7 - Sep 8

4. North Fork Resort

Greenport

Lisa

₩519,675 total

includes taxes & fees

Sep 7 - Sep 8

Apartment | Iron/ironing board, WiFi (free)

5. Montauk Oceanside Suites

Downtown Montauk

Carlos

₩345,554 total

includes taxes & fees

Sep 8 - Sep 9

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

6. Driftwood Resort

Montauk

William

₩424,916 total

includes taxes & fees

Sep 13 - Sep 14

7. The Surf Club

Montauk

Erica

₩628,831 total

includes taxes & fees

Sep 9 - Sep 10

One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

8. Offshore Spa & Residences

Downtown Montauk

"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...

Frank

₩1,696,667 total

includes taxes & fees

Sep 7 - Sep 8

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Top Wainscott Woods Hotel Reviews

Hampton's Vacation Inn

10/10 Excellent

"Loved our cottage and the well maintained grounds. Much better than the photos."

Beachcomber Resort at Montauk

8/10 Good

"Excellent location for a stay close to town but away from the crowding and across the street from the ocean with views of the sunrise from our room. The room was spacious and clean, and the full kitchen was a great resource for traveling with children. The per-person charge for the room felt like gouging in an area that is already a thousand dollars per night per room, with the meting out of individual bracelets to access the pool, the only resort amenity, which smacked of nickel-and-dime business strategy. I understand wanting to prevent 4 college kids from splitting a room and abusing the resort, but there is no distinction for families traveling with little ones."

Ocean Resort Inn

10/10 Excellent

"Fantastic place with a good location within town and walking distance to all shops and local restaurants. Rooms are modern and immaculate. Walls are thick enough where you don’t hear your neighbor which was a pleasant surprise. Cute sitting areas outside the rooms. The pool is large and the area is spacious and relaxing. Staff was extremely friendly and the price was not bad for the location. A little more of an ocean view would be nice, but one would have to pay a lot more for a true ocean view. I would definitely stay again!"

The Shoals Suites and Slips

10/10 Excellent

"The hotel was very clean with a lovely environment. The staff (especially at the front desk) were helpful, friendly, polite and very knowledgeable about recommendations for the area. The property was well maintained and the views were beautiful and very accessible to many activities in the area. Looking forward to return in the near future."

The Bentley Hotel Southampton

10/10 Excellent

"Peace, My Bentley hotel experience was superb! The staff is very hospitable, friendly, helpful, courteous and professional. The suite was very nice. I love the fact that you have to go through two securely locked, solid doors in order to get inside. I also loved the lay out, including the fact that there is a outdoor sitting area in the back which is connect to a big backyard. Although I did not get a chance to utilize much of the amenities, because I only stay one night, I plan on utilizing them the next time I visit. (smile)"

Find out more about Wainscott Woods

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Frequently asked questions

Can I find a vacation rental in Wainscott Woods?

Yes, we have vacation rentals near the most popular attractions in Wainscott Woods, or you can go with a secluded option if you want a relaxing place to stay.

How many vacation rentals are there in Wainscott Woods?

With 18 Expedia vacation rentals, you're sure to find just the right place for your Wainscott Woods stay.

What’s there to see and do in Wainscott Woods?

Explore the area and family-friendly sights such as Railroad Museum of Long Island, or get out into nature at a spot like Georgica Beach. Wolffer Estates Vineyard and The Jewish Center of the Hamptons are a couple of places you'll find in the larger area.

What’s a vacation rental in Wainscott Woods like?

A vacation rental is a private property you can stay in for a couple of days or more in Wainscott Woods. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Wainscott Woods vacation rentals

1. Windward Shores Ocean Resort

2. Cliffside Resort Condominiums

3. Montauk Manor

4. North Fork Resort

5. Montauk Oceanside Suites

6. Driftwood Resort

7. The Surf Club

8. Offshore Spa & Residences

Find vacation rentals that suit your style

Top Wainscott Woods Hotel Reviews

Hampton's Vacation Inn

Beachcomber Resort at Montauk

The Atlantic Hotel

Ocean Resort Inn

The Shoals Suites and Slips

Offshore Montauk

Kenny's Tipperary Inn

The Bentley Hotel Southampton

Find out more about Wainscott Woods

Frequently asked questions

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