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Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

Photo gallery for Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

Living Room
Living Room
Dining Room
Kitchen
Kitchen and walk-in pantry

Reviews

9.8 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 14325.2 sq m

Popular amenities

  • Hot tub
  • Parking available
  • Dryer
  • Pet-friendly
  • Washer

Explore the area

View map
Wainscott, NY
  • Place, East Hampton Main Beach
  • Place, Wolffer Estates Vineyard
    ‪5 min drive‬
  • Place, Georgica Beach
    ‪9 min drive‬
  • Airport, East Hampton, NY (HTO)
    ‪5 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Cottage: Guest Room #1

1 Double Bed

Cottage: Guest Room #2

1 Queen Bed

Cottage Living Room

1 Double Futon

Main House: Lower Level Master Bedroom

1 King Bed

Main House: Upper Level Guest Bedroom

1 King Bed

Main House: Upstairs Master

1 King Bed

Media Room: Large room with brand new pull out sofa and TV

1 Double Futon

4 bathrooms, 1 half bathroom

Cottage: Main Bathroom

Toilet · Shower only

Main House: Lower Level Master (En-Suite)

Toilet · Shower only

Main House: Powder Room

Toilet

Main House: Upstairs Bathroom

Toilet · Shower only

Outdoor Shower

Shower only · Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Kitchenette
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

Welcome to Wainscott!

Discover the authentic Hamptons at this 1.5-acre Wainscott vacation rental, a historic compound perfect for family reunions, friends sharing, or multi-generational getaways. Once home to a founding farmer, this shingle-style estate blends timeless charm with modern luxury across a main villa and guest villa (3,500 sq. ft., sleeps 14 with pull-out couches). Two independent houses on one lot is a rarity for the Hamptons.

Steps from Wainscott’s pristine beach, this south-of-the-highway haven offers a brand new Hot Tub Jacuzzi, lap pool, childproofed grounds, and unobstructed farmland views—ideal for extended families with in-laws, staff, or grandchildren.

Property Highlights

Main Villa: 3 bedrooms, 3 bathrooms, gourmet kitchen, indoor fireplace, deck with designer furniture, hot tub and lower floor media room.

Guest Villa: 2 bedrooms, 1 bathroom, kitchen, cozy lounge, private patio—perfect for privacy.

Family-Friendly: Childproofing, pool fence with safety latches, enclosed courtyard, crib/high chair (on request), and dog-friendly (with approval).

Luxury Amenities: 2024 Hot Tub, indoor/outdoor fireplaces, Sonos surround sound, high-speed Wi-Fi, reclaimed farm floorboards, s'mores pit, lap pool, multiple decks and outdoor dining opportunities.

Outdoor Oasis: Landscaped grounds (bug/tick-treated), BBQ area, and stunning westerly sunset views.

Why Families Love It
Walk to Wainscott’s exclusive beach (permit parking) or a renowned farm stand. Enjoy crashing waves, birdsong, and occasional opera serenades from our Viennese neighbor. Close to “The Clubhouse” where you can enjoy Padel, bowling, arcade games and mini golf.

With two homes for the price of one elite retreat, this compound offers unmatched value for groups, blending historic charm with modern comforts.

Security includes a monitored alarm, discreet cameras, and emergency systems.

Practical Details
Weekly discounts available—ask us!
Groups over 8 need approval ($200 extra cleaning fee).
(Visa/Mastercard/Debit, no AmEx).
24/7 support and keyless check-in.

Book Now
Secure this Wainscott family retreat for an unforgettable Hamptons escape! Contact us for exclusive off-season rates or instant book today.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Child proofed house but extra supervision a must
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Events

Events allowed: family gatherings and birthday parties
With written approval, extra fee and no loud noise
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Pets

Pets allowed: dogs and cats (limit 2 total)
$500 pet fee for one and $750 for two-three pets.
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Smoking

Smoking is not permitted
Payment rules: Travelers name on their payment method must match the name on the VRBO booking, ID and lease agreement. Amex not accepted.
Bookings are one week minimum.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 30
Note from host: With written approval, extra fee and no loud noise
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
Property Registration Number 20-1775

We should mention

This property does not have any lifts

About the area

Wainscott

Located in Wainscott, this holiday home is in a rural area and near the beach. SagPond Vineyards and Wolffer Estates Vineyard are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Madoo Conservancy and South Fork Natural History Museum and Nature Center. Travelling with kids? Consider Children's Museum of The East End and Jonathan Adler. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Wainscott, NY

What's nearby

  • Wolffer Estates Vineyard - 5 min drive - 3.9 km
  • The Jewish Center of the Hamptons - 6 min drive - 5.4 km
  • Guild Hall - 8 min drive - 6.4 km
  • Georgica Beach - 9 min drive - 6.0 km
  • LongHouse Reserve - 12 min drive - 8.8 km

Getting around

  • Bridgehampton Station - 7 min drive
  • East Hampton, NY (HTO) - 5 min drive

Restaurants

  • ‪Common Ground East - ‬5 min drive
  • ‪Highway - ‬3 min drive
  • ‪La Capannina - ‬12 min walk
  • ‪Townline BBQ - ‬19 min walk
  • ‪The Wine Stand - ‬3 min drive

Frequently asked questions

Does Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub! pet-friendly?

Yes, this property allows cats and dogs (limit 2 total). Some restrictions may apply, so please contact the property for more details.

What time is check-in at Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!?

Check-in begins at 3:00 PM.

What time is check-out at Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!?

Checkout is at 11:00 AM.

Where is Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub! located?

This family-friendly Wainscott holiday home is located by the sea, within 3 mi (5 km) of Wolffer Estates Vineyard, Madoo Conservancy and SagPond Vineyards. South Fork Natural History Museum and Nature Center and Children's Museum of The East End are also within 6 miles (10 km).

Reviews

9.8

Exceptional

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.6/10

Listing accuracy
Rating 10 - Excellent. 28 out of 29 reviews
Rating 8 - Good. 0 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 1 out of 29 reviews

Reviews

10/10 Excellent

Seth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hamptons escape

The whole process was seamless. The owner was accessible and responsive. A tremendous property with a luxurious location. Highly recommend!!
Stayed 7 nights in Aug 2025

10/10 Excellent

Leigh E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property, excellent property manager

Thoroughly enjoyed our stay, property manager was incredibly helpful and responsive, highly recommend!
Stayed 5 nights in Apr 2025

10/10 Excellent

Janet D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wainscott Family Visit

Very comfortable and lovely accomodations; wonderful property with amenities - close to beach and heart of Wainscott. Appreciated the host and property manager's responsiveness to small questions.
Stayed 4 nights in May 2025

10/10 Excellent

Scott S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

As advertised

Accurate photos. Great property and location
Stayed 7 nights in Jun 2024

10/10 Excellent

Catherine D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for a family

Perfect location for a family trip! Great property to just hang by the pool & enjoy the large back yard. Nice bike ride past a farm stand to get to the beautiful beach. Love the surrounding farms & proximity to the beach
Stayed 7 nights in Aug 2020

10/10 Excellent

Warren C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sayres Path

The property, location and weather could not have been more perfect for us. I would stay there again without hesitation.
Stayed 14 nights in Sep 2019

10/10 Excellent

Weston F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

Whole place is awesome.....nice piece of property with plenty of room for our toddler and dog to run around. Pool was great. House was super clean. Close to the beach....bikes were helpful. Also super convenient to seafood/steak shopping. Would def go back. Host was also super easy/responsive.
Stayed 2 nights in Jul 2024

10/10 Excellent

Michael H., New York City

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Home

Such a beautiful home tucked away in a quiet neighborhood. Ben was very flexible and responsive throughout our entire stay. The backyard is truly breathtaking. Just go!
Stayed 6 nights in May 2021

2/10 Terrible

Amy K.

Liked: Check-in, communication
Disliked: Cleanliness, location, listing accuracy

The WORST! RUN!

So my husband and I rented this property for 12 days. Initial communication with Ben ( who lives in London) was great and easy. We have been renting in the Hamptons for 23 years and know the area ( which is nice). The house itself was not ready to be rented 1. Bugs all over cottage2. Master bedroom sheets blankets stained3. Sun protection umbrellas were not operational by the pool and because they didn't have a base - they put rocks on it to keep the umbrella from falling over. Well it didn't work and they fell over and almost hit my mom. They were told by the house manager multiple times, but the owner didnt fix the problem. The house manager was lovely and helpful, but the owner got in the way of her ability to fix it.4. He has vanished with my refundable deposit and wont reply. VRBO gives no protection, so we are out of luck! I cant say it enough- RUN AWAY FROM THIS LISTING FAST!
This was the moldy shower curtain in the bathroom
This was one of the dtained blankets
Here is the pool umbrella which had fallen ( no wind)
Same
Stayed 10 nights in Jul 2025

10/10 Excellent

Matthias K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property is simply extraordinary—far beyond what we could have wished for. From the secluded house and expansive garden to the long pool and private hot tub, every detail feels thoughtful and refined. The tasteful interior, endless supply of fresh towels, and sweeping views in the heart of the Hamptons made our stay unforgettable. We cannot wait to return!
Stayed 4 nights in Sep 2025

10/10 Excellent

Gia T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

Wonderful all the way around!
Stayed 14 nights in Jun 2022

10/10 Excellent

Hugh A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall in the Hamptons

Great location. House was just as advertised. Response time from owner and property manager was excellent. Definitely will return.
Stayed 7 nights in Oct 2022

10/10 Excellent

Lisa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location Hamptons House

If you are looking for a nicely renovated Hamptons house that is centrally located to East Hampton, South Hampton, and Sag Harbor, this will be perfect for you! It can comfortably fit 8-10 people, has a beautifully landscaped yard with a pool that overlooks a lovely farm, and is a doable walk to the beach. We thoroughly enjoyed our stay here and would definitely come back again! Thank you from The Houstonians!
Stayed 7 nights in Jun 2022

10/10 Excellent

Dana G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful central Hamptons getaway

The home was beautiful and appointed with everything we needed. 1.2 mile walk to the beach, though off-season, was gorgeous. We can’t wait to go back!
Stayed 5 nights in May 2022

10/10 Excellent

Rachel P., New York City, NY

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely home in great location

We had a nice relaxing stay at this house. It’s centrally located and close to the ocean. The downstairs bed was incredibly comfortable. Beautiful yard with plenty of room for my pup to run around. Owner and property manager were both very helpful and responsive. Would happily come back!
Stayed 6 nights in Apr 2022

10/10 Excellent

Aracelis T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing residence

We had a phenomenal experience at this property! We brought two small dogs that enjoyed the large backyard area. While the weather outside was quite cold, the house was cozy the entire time. We also managed to use the outdoor hot tub. Would highly recommend!
Stayed 5 nights in Jan 2022

10/10 Excellent

Chris S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and a Great Location

The stay worked perfectly for us. The property is quiet and on a beautiful street with an easy walk to the beach. The beach is lovely and on the quieter side. We filled the cottage and the main house and everyone was happy. The property is quiet and the outside areas and pool very relaxing. A highlight was late afternoon as the sun goes down over the deep backyard and pool. The kitchen is well equipped with plenty of fridge space and a nice gas cooktop. Local restaurants are varied and well above average. And truly the master bed on the main floor was the most comfortable bed I gave ever slept on.
Stayed 7 nights in Jul 2021

10/10 Excellent

Elizabeth S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy beach house in a great location

This house was the perfect place for our family to gather. It’s very conveniently located to the beach in town, and the property is beautiful!
Stayed 7 nights in Jun 2021

10/10 Excellent

Lisa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

House in Wainscott

Lovely home in The Hamptons.
Stayed 6 nights in May 2021

10/10 Excellent

Jessica S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Getaway!

We had an amazing Spring Break week at the house. It was great for our family - 2 adults, 2 kids, 2 grandparents and a dog. The main level bedroom was perfect for my parents, the layout of the house worked great with the extra tv room for the kids downstairs. Having the yard completely fenced in was an extra comfort for letting our old dog walk the property each morning and letting the kids roam, and the main living area/kitchen that led out to the deck was perfect for having a morning coffee, doing activities or an afternoon cocktail looking over the fields. Located on Sayres Path, it's close to town, walking distance to a great beach and on the farm side of the road which gives amazing views! We used the extra cottage as an office - but I'm sure when the pool is open it's a perfect extra living space. The owners were really helpful and check in/check out was easy. And we loved having the hot tub! Overall a fantastic place to get away - the kids can't wait to come back to use the pool!
Stayed 6 nights in Mar 2021

10/10 Excellent

Madison W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property and great hosts

This was a beautiful property. It had everything we needed. The furniture and beds and linens were lovely. The steam shower was incredible. We had an amazing time.
Stayed 4 nights in Feb 2021

10/10 Excellent

Alison S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

We had such a wonderful long winter weekend in this beautiful home. We felt at ease bringing a 1 and 2 year old with all of the childproofing. The location was perfect, close to the beach and an easy drive to all of the Hampton’s hot spots. We look forward to renting this fantastic house again in the summer to utilize the pool and hit up the beach!
Stayed 4 nights in Nov 2020

10/10 Excellent

Kimberly D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular setting

Visited here in winter with our two children. Well appointed home, spacious lawn, beautiful sunsets. The neighborhood and location were great, we enjoyed walking to the beach and the local restaurants. Very comfortable and relaxing stay! Would visit again!
Stayed 6 nights in Dec 2020

10/10 Excellent

Beatriz G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location and a very cosy house.

Set on a perfect location, the house is very cosy and charming, perfect for a family relaxed gathering. The oven was perfect for my Turkey! Host was really helpful at all times.
Stayed 5 nights in Nov 2020

10/10 Excellent

Eric R., New York, NY

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Property

Incredible location, incredible yard, very charming, nice and well-equipped house. Owner very easy to work with.
Stayed 4 nights in Oct 2020

About the host

Hosted by Ben

Host profile image
We are New Yorkers and this is our family home.

Why they chose this property

This is as classic as Hamptons properties come - this particular property has been around for 100+ years. While we know that this property will rent quickly, we will only consider discerning and respectful families.

What makes this property unique

-Spectacular south of highway location
-Tonnes of light and open space
-Unobstructed farm views
-Sunsets
-Local farmstead is walking distance
-Extra Large 65 foot Lap Pool
-TWO homes on one piece of land which is ideal for larges families, those that like to host and/or those with domestic employees.
-Excellent beach in walking distance
-Brand furniture and decor
-All mod cons
-Organized and clean
-Enhanced security measures

Languages:

English
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