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Rare 2-House Compound - Wainscott South of Hwy - Walk to Beach - Pool & Hot Tub!

Photo gallery for Rare 2-House Compound - Wainscott South of Hwy - Walk to Beach - Pool & Hot Tub!

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

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Top rated beach location
    Discover paradise at this top rated beach location.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade and game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
5 bedrooms4+ bathroomsSleeps 14

Popular amenities

  • Balcony
  • Spa pool on site
  • Private pool
  • Kitchenette
  • Barbecue
  • Free Wi-Fi

Explore the area

View map
Wainscott, NY
  • Place, The Hamptons Beaches
    ‪3 min drive‬
  • Place, Shinnecock Hills Golf Course
    ‪25 min drive‬
  • Place, Cooper's Beach
    ‪27 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

Rare 2-House Compound - Wainscott South of Hwy - Walk to Beach - Pool & Hot Tub!

Welcome to Sayres Path, Wainscott — South of the Highway

Two separate, self-contained homes on a single lot — one of the last true family compounds in the Hamptons.

A fully independent main house and guest cottage on a single 1.5-acre estate — grandfathered-in, irreplaceable, and perfectly suited to families who want to be together without being on top of each other.

Once home to a founding Wainscott farmer, this historic shingle-style estate has been thoughtfully updated for modern living — reclaimed farm floorboards, a 2024 hot tub, heated lap pool, and designer finishes throughout — while retaining the soul of a true Hamptons retreat. 3,500 sq. ft. across both houses, sleeping up to 14.

Close to the beach. South of the highway. Unobstructed farmland views to the horizon.

The Property

Main House: 3 bedrooms, 3 bathrooms, gourmet kitchen, indoor fireplace, media room with pull-out couch, designer decks, hot tub

Guest Cottage: 2 bedrooms, 1 bathroom, full kitchen, private lounge, independent deck

Grounds: 1.5 acres, heated lap pool, BBQ, s'mores pit, multiple outdoor dining areas, westerly sunset views and total peace.

Bug and tick treated throughout

For Families
Pool fence with safety latches, enclosed courtyard, crib and high chair on request, dog-friendly with approval. The cottage offers genuine independence for in-laws, older children, or staff — without anyone feeling separated from the heart of the house. Walk to Wainscott Beach (permit parking), a celebrated local farm stand, and a short drive to The Clubhouse — Padel, bowling, arcade, and mini golf.

Luxury Amenities
2024 hot tub, indoor and outdoor fireplaces, Sonos surround sound throughout, high-speed Wi-Fi, reclaimed hardwood floors, keyless entry, monitored security system.

Practical Details:

Longer stay discounts available — enquire directly
Groups over 8 require prior approval ($200 additional cleaning fee)
Visa, Mastercard and Debit accepted — no AmEx
24/7 guest support throughout your stay

Add dates for prices

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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

Property Registration Number 20-1775
Property # 734710vb
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

About the area

Wainscott

Located in Wainscott, this holiday home is in a rural area and near the beach. While the natural beauty of The Hamptons Beaches and Cooper's Beach can be enjoyed by anyone, those looking for an activity can explore Shinnecock Hills Golf Course. Travelling with kids? Consider Madoo Conservancy and South Fork Natural History Museum and Nature Center. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and cycling nearby.
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Map
Wainscott, NY

What's nearby

  • The Hamptons Beaches - 3 min drive - 2.9 km
  • The Jewish Center of the Hamptons - 6 min drive - 5.7 km
  • Shinnecock Hills Golf Course - 25 min drive - 25.0 km
  • Cooper's Beach - 27 min drive - 22.5 km
  • Montauk Point - 45 min drive - 44.6 km

Getting around

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

Restaurants

  • ‪Starbucks - ‬6 min drive
  • ‪The Wine Stand - ‬3 min drive
  • ‪Round Swamp Farm - ‬6 min drive
  • ‪Townline BBQ - ‬19 min walk
  • ‪La Capannina - ‬12 min walk

Frequently asked questions

Does Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | Pool & Hot Tub have a pool?

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

Is Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | 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.

How much is parking at Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | Pool & Hot Tub?

On-site parking is available at the property.

What time is check-in at Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | Pool & Hot Tub?

Check-in begins at 3:00 PM.

What time is check-out at Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | Pool & Hot Tub?

Checkout is at 11:00 AM.

Where is Rare 2-House Compound | Wainscott South of Hwy | Walk to Beach | Pool & Hot Tub located?

This family-friendly Wainscott holiday home is located by the sea, within 2 mi (3 km) of The Hamptons Beaches and The Clubhouse Hamptons. Madoo Conservancy and Wolffer Estates Vineyard are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 29 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. 0 out of 29 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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
Response from VrboOwner on 30 May 2025
Please come again soon, Leigh- you need to experience a Wainscott summer. Thank you for the kind review
Verified

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
Response from VrboOwner on 10 June 2026
Thank you for taking the time to review- you were wonderful guests. Please come visit again.
Verified

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
Response from VrboOwner on 30 May 2025
Delighted you enjoyed your stay. Please come join us in Wainscott again.
Verified

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
Response from VrboOwner on 8 October 2020
Catherine, we're happy you enjoyed your stay and it was a pleasure having you and your family at the property.
Verified

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
Response from VrboOwner on 21 April 2026
Thank you to you and your family- you were a joy to host. We are delighted you enjoyed our home as much as we do.
Verified

10/10 Excellent

Kennedy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about this property is absolutely amazing! Me and my sister did a girls trip and stayed at this stunning Vrbo. It was incredibly clean, the location was amazing, the hot tub was fantastic, the kitchen has everything you need and more, the beach is a 2 minute drive, etc. (I could go on and on!). I felt at home staying in this gorgeous place. I’ll definitely be staying here anytime I go back to the Hamptons. Not only that.. but the host (Ben) was incredibly responsive from start to finish. He checked in with us to make sure we got in okay, etc. This is the most ideal place to stay if you’re visiting the Hamptons! It’s so close to everything. If you’re planning a trip to the Hamptons.. do yourself a favor and book this Vrbo.. you’ll absolutely love it!! Can’t wait to come back. Thank you for everything, Ben!!
Stayed 3 nights in Apr 2026
Response from VrboOwner on 10 June 2026
Thank you for the thoughtful review, Kennedy. You were a delight. Please come join us again. We love welcoming back our returning renters.
Verified

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
Response from VrboOwner on 30 March 2020
Thank you for the compliments, Warren. We are so glad you enjoyed our special home as much as do.
Verified

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
Verified

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
Verified

10/10 Excellent

Michael H.

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
Verified

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
Response from VrboOwner on 30 May 2025
Delighted you enjoyed your stay. Please come join us in Wainscott again.
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Rachel P.

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Eric R.

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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