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Heart of Westhampton Village

Family-friendly holiday home with fitness centre and outdoor pool

Photo gallery for Heart of Westhampton Village

Completely encircled by hedges Silver Oaks is a secluded--room to relax & play!
Alfresco dining for 10-14 on the covered deck
Glass-covered deck makes for lovely lounging & dining, rain and shine.
Gourmet kitchen with double oven, gas range, two sinks, 2 fridges & dishwasher.
Kitchen is spacious & fully equipped—fab for group meal prep and casual dining.

Reviews

10 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 10325.2 sq m

Popular amenities

  • Parking available
  • Gym
  • Dryer
  • Washer
  • Barbecue grill

Explore the area

View map
  • Place, Westhampton Beach Performing Arts Center
  • Place, Long Island Aquarium and Exhibition Center
  • Place, Splish Splash Water Park
  • Airport, Westhampton, NY (FOK-Francis S. Gabreski)

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 1

1 Queen Bed

Bedroom 1

1 Queen Bed

Bedroom 1

1 Queen Bed and 2 Cribs

Bedroom 1

1 Queen Bed

5 bathrooms

Basement Bathroom

Toilet · Shower only

Grey Room en suite bath

Toilet · Shower only

Main floor handicap accessible bath with grab bars

Toilet · Shower only

Master en Suite

Toilet · Shower only · Jetted bathtub

Turtle Room en suite

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Heart of Westhampton Village

Be near everything in this completely updated 3700 sq foot home surrounded by lush grounds and high hedges. Super high-end whimsical furniture abounds. Living area and kitchen opens onto a glass-covered deck with comfy lounge area and dining table looking over the large pool and deck area. Handicap accessible with ramp and first floor bedroom with on-suite handicap accessible bathroom & shower. Three upstairs bedrooms and basement also feature on-suite bathrooms. Gourmet kitchen with double oven, wine fridge, microwave and prep island. Private backyard with heated pool, propane grill and fire pit, poolside bathroom with shower, perfect for entertaining. There's even a half-sized basketball court, bacci ball and badminton.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

No events allowed
With pre-approval.
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Gather used towels
Remove personal items
Turn off the lights, lock the doors and return the keys
Check out is noon: -leave beds unmade -leave used towels hanging, either in the bathrooms or on the fence in the laundry room. -remove any/all tape & decorations you may have brought.
- take the food/drink items you want-leave what you don’t (the cleaning staff will donate or discard what’s left. -double-check you have all the belongings.
-lock all doors and windows. -text when you leave. We hope you all are having a marvelous time! Thank you, Kelly
Failure to complete these may result in a negative review from the host.

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
On-site parties or group events are strictly prohibited
Note from host: with pre-approval.
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

We should mention

This property does not have any lifts
A car is not required for transport to and from this property

About the area

Westhampton Beach

Located in Westhampton Beach, this holiday home is by the sea. Harbes Family Farm and Tanger Outlet Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Baiting Hollow Hummingbird Sanctuary and Hallock State Park Preserve. Travelling with kids? Consider All Star Bowling and Safari Adventure. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Westhampton BeachOpens in a new window
Map
Westhampton Beach, NY

What's nearby

  • Westhampton Beach Performing Arts Center - 12 min walk - 1.1 km
  • The Hamptons Beaches - 3 min drive - 3.9 km
  • Long Island Aquarium and Exhibition Center - 10 min drive - 14.2 km
  • Tanger Outlet Center - 17 min drive - 23.8 km
  • Splish Splash Water Park - 17 min drive - 24.8 km

Getting around

  • Westhampton Station - 2 min drive
  • Westhampton, NY (FOK-Francis S. Gabreski) - 3 min drive

Restaurants

  • ‪One Trick Pony - ‬14 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪Fauna - ‬15 min walk
  • ‪The Ketch - ‬2 min drive
  • ‪Eckart's Luncheonette - ‬6 min walk

Frequently asked questions

Does Heart of Westhampton Village have a pool?

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

Is Heart of Westhampton Village pet-friendly?

No, pets are not allowed at this property.

How much is parking at Heart of Westhampton Village?

On-site parking is available at the property.

What time is check-in at Heart of Westhampton Village?

Check-in begins at 4:00 PM.

What time is check-out at Heart of Westhampton Village?

Checkout is at 12:00 PM.

Where is Heart of Westhampton Village located?

This family-friendly Westhampton Beach holiday home is located by the sea, within 2 mi (3 km) of Westhampton Beach Performing Arts Center and Moriches Bay. Lashley Beach and The Hamptons Beaches are also within 3 miles (5 km). Westhampton Station is 20 minutes by foot.

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 74 out of 74 reviews
Rating 8 - Good. 0 out of 74 reviews
Rating 6 - Okay. 0 out of 74 reviews
Rating 4 - Poor. 0 out of 74 reviews
Rating 2 - Terrible. 0 out of 74 reviews

Reviews

10/10 Excellent

Sid S.

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

Beautiful home, perfect for a weekend away!

The main house and pool house were lovely and perfect for the weekend! We had an amazing time sitting by the pool all weekend
Stayed 3 nights in Jul 2025

10/10 Excellent

Kacey F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect house for our sibling trip! 10 of fit perfectly. The backyard is heaven on earth and we loved walking into town every day. Kelly was so accommodating and responsive!
Stayed 4 nights in Aug 2025

10/10 Excellent

Diane R., Queens, New York 11414

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

Perfect "home away from home"

Beautiful home filled with delightful decor and artwork, comfortable furnishings, a bath room for every bedroom, large kitchen with every cooking item imaginable and plenty of room for family to gather. Covered outdoor dining and seating, pool, not far from beach, walk to town, Gardening paradise !!!!!
Stayed 6 nights in Sep 2022

10/10 Excellent

Aileen Grace A.

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

Wonderful home for families

Kelly's home was truly a home away from home. It had all the amenities one could need, especially for little ones. Truly did not need to pack anything other than clothes. Communication with Kelly was exceptional, she was very warm and inviting and helpful with any questions we had along the way. Highly recommend booking this place and I know we'd go back.
Stayed 5 nights in Aug 2024

10/10 Excellent

Ruby S.

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

Wonderful stay and host!

Our trip at Kelly’s property was nothing short of perfect. The house itself was everything we imagined and more, and Kelly’s communication was fantastic! She provided such great recommendations, detailed information on everything needed in the house, and was constantly available if anything came up. Looking forward to going back next summer!!
Stayed 3 nights in Aug 2023

10/10 Excellent

Kira H.

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

Perfect weekend stay

If you’re thinking of renting Kelly’s house, do it. She is the most gracious host, incredibly thoughtful and her house is beautiful. Our group had plenty of room for all of us and we had the best time. Thank you again for everything Kelly!
Stayed 3 nights in May 2021

10/10 Excellent

Aliza M.

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

Family Vacation

This is our second stay at this house. Every time I think we have found everything we could possibly need, we find more gear to make our vacation even better! I can't begin to describe how great this place is. I hope we will have the privilege of spending time here in the future.
Stayed 8 nights in Aug 2023

10/10 Excellent

Lee S.

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

Perfect family getaway

Had the best family weekend in Kelly's house in Westhampton beach. The house had everything you could dream of. A great pool, BBQ, and outdoor furniture. Huge kitchen with any kind of appliance and tool. Multiple media rooms, games, and lots of space. Would definitely return again. Hopefully soon
Stayed 3 nights in Sep 2023

10/10 Excellent

Alexis N.

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

Wonderful getaway!

From start to finish everything was perfect. The house was very clean, the kitchen was perfect had everything you would need to cook a gourmet meal. The pool, patio, outdoor refrigerator is just what you need on a hot day. The whole experience was very child friendly.The grounds were beautiful. Kelly was so easy to get in touch with. We had a wonderful time!
Stayed 3 nights in Aug 2021

10/10 Excellent

Karen R.

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

Wedding and Family Fun Fest!

My husband and I and our 3 adult children with their spouses and our 2 grandchildren had an amazing weekend at this extraordinary home. It was the perfect proximity to the Ocean Blue wedding venue we attended on Saturday.Aside from this beautiful location, this home is stunning and the hosts are extremely accommodating with all amenities. We all enjoyed the beautiful and unique decor as well as the library of books and music to listen to.Kelly and Curtis are exceptionalHosts and everything was perfect and beyond.I am so glad that we all were able to gather and experience this home and property for the time we were there. Our children live in three different states and don’t see each other as much as they’re like to or we would like . We made special memories as we used the pool, basketball/ pickleball court, the outside grill and coffee area. It was great fun playing trivia on the beautiful backyard deck after the sun went down. Thanks for the memories!Don’t hesitate to book if you are lucky enough to find this home available.
View from half basketball court
Stayed 3 nights in Jun 2025

10/10 Excellent

Katie K.

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

Can't express how lovely this home is!

We stayed here as a group of 8 friends, and we loved everything about our stay! There was plenty of sleeping space and bathroom space for all of us, and we easily could have had a few more stay with us comfortably. The pool and backyard are picturesque, and we certainly took advantage of the pool during the heatwave when we were there! It was all really well-equipped too. They had towels, pool floats, yard games, board games, and really just about everything we needed for our trip. The kitchen was large and great for cooking or just chatting around the island. And the entire house had such great character – we really felt at home here during our short stay and wished we could have stayed longer! The downtown area of Westhampton Beach was a quick walk away, and we loved having such a great main street area nearby. There was even a nice farmer's market in town on Saturday while we were there. Communication with the host was always prompt and friendly. We really only have great things to say about this property. I am already trying to find an excuse to stay here again in the future! If this is available, don't hesitate to book it! You won't regret it!
Stayed 3 nights in Jun 2025

10/10 Excellent

Joyce L., Brooklyn, NY

Great Pool and Bathrooms for All

We rented Silver Oak for a long weekend for a group of 10 adults and 1 baby. It was the perfect house for our group. We spent most of our time at the pool where there are loungers, a grill, an extra fridge, and of course a big pool. Seems silly for me to call out bathrooms for all, but when there are 5 couples it makes total sense. There is a full bath connected to each bedroom. Kitchen is perfect for cooking for a big group. If you need it, there is also a crib at the house. The house is uniquely decorated and tied to different cultures from around the world.
Stayed 3 nights in Jul 2018

10/10 Excellent

Rebecca O.

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

Writing oasis

Wonderful spot for a productive and relaxing getaway with fellow women writers! It's a beautiful property with gardens and art and treasures throughout the interior as well as outside - inspirational for creativity and calm all at once. The pool and patio and deck were lovely and still so summery deep into September. Very easy to find space to work undisturbed as well as be together as a group. We were a group of four and each had our own bedroom and bathroom space - this would have also been true if we were six! Kelly was an amazing host - welcoming and thoughtful and clear. Everything was impeccably clean, well appointed, interesting, and comfortable, and we wanted for nothing. We departed thankful for the stay, refreshed, and with many happy memories of the home and surroundings. Thank you, Kelly & co!
Stayed 3 nights in Sep 2023

10/10 Excellent

Allison K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool / backyard was excellent. Good space for each couple with room bathroom. Kelly was super responsive and made sure everything went well!
Stayed 3 nights in Sep 2025

10/10 Excellent

Theresa D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy check in process. Kitchen was well stocked and hosts were gracious with use of cooking supplies.
Stayed 4 nights in Aug 2025

10/10 Excellent

Sara C.

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

Incredible Host and Gorgeous Property!

We rented this beautiful home for our wedding weekend, and it was absolutely perfect for our extended family. The property is even more stunning in person—spacious, impeccably maintained, and full of charm. Every bedroom having its own bathroom was such a bonus and made it incredibly comfortable for all of our guests.Kelly, the host, was phenomenal—so responsive, kind, and helpful every step of the way. She made the entire process seamless and stress-free, which we appreciated so much during such a busy weekend.The kitchen and living spaces were ideal for gathering, and the backyard was the perfect place for folks to relax in between wedding festivities.We’re so grateful to have found this gem and would recommend it without hesitation to anyone looking for an elegant and comfortable home close to downtown West Hampton Beach. Thank you, Kelly, for helping make our wedding weekend so special!
Stayed 3 nights in May 2025

10/10 Excellent

Judah I.

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

Wonderful place

Beautiful, spacious, well kept
Stayed 11 nights in Apr 2025

10/10 Excellent

Steve M.

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

Exceptional stay

Great loc. for our 5 couple group. Kitchen, porch and common areas plenty big for our group of 10. Beds were comfortable. Yard and pool area were impeccably landscaped. Fire pit setup was great (an important item for our group). Modern features for minimal waste stream. Would return without hesitation.
Stayed 3 nights in Oct 2024

10/10 Excellent

Linda C.

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

September Sojourn

Silver Oaks is more of a luxury hotel than a home rental. Kelly and Curtis anticipate guests’ every need as well as those we didn’t anticipate having [croquet, bicycles, badminton, pool floats]… The outdoor space is perfect for lounging, dining, and cooking; the bedrooms and bathrooms are comfortable and well-appointed; and the kitchen perfectly suited our group of ten, as we prepared all of our meals there during our 4-day stay. Kelly is the ultimate communicator, and answered our many questions almost immediately. We were blessed with perfect weather, but the house offers many indoor gathering spaces for those who need them.
Stayed 4 nights in Sep 2024

10/10 Excellent

Barb J.

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

Inspired home for a large gathering

Fabulous accommodations for our family traveling from the west coast to attend a wedding celebration in WHB. Loved the home and cottage decorated with finds from far flung travel, pool, bikes, lounge chairs, outdoor eating… Everything we needed to make our family gathering easy and relaxing. Highly recommended!
Stayed 4 nights in Sep 2024

10/10 Excellent

Aliza M.

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

A wonderful Family Getaway

We enjoyed our stay for the third summer in a row. The hosts are beyond amazing. There isn't enough space here for me to describe how perfect the place is for us!
Stayed 4 nights in Aug 2024

10/10 Excellent

Vinny R.

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

Amazing Weekend

We got to celebrate my wife’s 40th birthday in style! The house was amazing, clean and an incredible experience all around to enjoy a big life milestone with friends. We couldn’t recommend this home more and Kelly was an incredible host!
Stayed 3 nights in Aug 2024

10/10 Excellent

Diane R.

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

Family retreat paradise

This was the 4th year my sister and I along with our family of children and grandchildren spent a week at Silver Oaks. Walk to town, close to WestHampton Beach, glorious garden, built in pool, covered outdoor patio. Inside is a treasure trove of antiques, artwork and pieces from all over the world. Chef’s kitchen, 5 beds with 5 baths. Toys for the kids, beach supplies, you name it, Silver Oaks had it. The host is a delight to work with. We wouldn’t stay anywhere else in the Hamptons. Already looking forward to next summer !!!!!
Stayed 6 nights in Jul 2024

10/10 Excellent

Christina C.

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

Absolutely perfect!

We had such a wonderful experience staying at Kelly’s house! The house is absolutely stunning! The backyard felt like an oasis with the privacy trees, pool, and covered patio. We were a group of 10 and there was plenty of seating inside and outside for all of us to sit in the same room at the same time and even around the dining room table. Kelly was so quick to respond, checked in to make sure everything was to our liking, and even left us some local wines to try in the fridge. There were a lot of little personal touches to ensure the house had everything we could possibly need. This couldn’t have been a better experience and we are hoping to come back soon!
Stayed 3 nights in Jul 2024

10/10 Excellent

Randi R.

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

Loved staying at Silver Oaks

We were a group of 10 friends, and the house was perfect for us. Equipped with amenities such as a basketball court and a wonderful pool, there was no shortage of activities. Silver Oaks was the perfect blend of fun and relaxation. The house is beautiful, comfortable, charming, and well-maintained. Kelly, the host, was welcoming and kind. We look forward to staying there again.
Stayed 5 nights in Jul 2024

About the host

Hosted by Kelly Bennett

Host profile image
After years living abroad and traveling the world, it was time to settle down. We knew what we wanted--and search both coasts until we found it! Westhampton Beach is a charming village near shops, banks, post office, services & restaurants, so we rarely have to drive; near the ocean so we can smell the salt breezes, swim, kayak and stoll in the sand; near wineries and farms so we can dine farm to table; near enough to the City we can train in for plays and cultural events; near enough to airports we can jet wherever we fancy (friends & family can easily visit); near enough to heaven.

Why they chose this property

A secluded resort in the heart of the village. Walk or bike everywhere--shops, play ground, movie theatre, restaurants and the beach!

Ours is a large multi-generational family, so it is usual, especially during the season and holidays, for 15-20 guests to visit. Thus being, we have created a home with inviting spaces to comfortably accommodate larger groups.

What makes this property unique

Completely surrounded by high hedges, it's truly an oasis. The glass-roofed pergola covering the large deck is lovely for relaxing and entertaining. The pool is large enough to swim laps or play games. The terracotta paved pool area and grape arbor offer comfortable lounging spots for sun and shade worshipers. When the sun sets, gather around the fire pit to chat and stargaze.

Languages:

English

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