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Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”

Photo gallery for Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”

Aerial view
Outdoor shower installed 2023
Detached garage / gym front view
Backyard view of the house
Basement

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
4 bedrooms3+ bathroomsSleeps 8

Popular amenities

  • Balcony
  • Spa pool on site
  • Private pool
  • Toys
  • On-site fitness centre
  • Barbecue

Explore the area

View map
Southold, NY
  • Place, Custer Institute and Observatory
    ‪4 min drive‬
  • Place, Croteaux Vineyards
    ‪4 min drive‬
  • Place, Sparkling Pointe
    ‪6 min drive‬
  • Airport, New London, CT (GON-Groton - New London)
    ‪152 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Basement

1 Queen Bed

Guest bedroom

1 Queen Bed

Guest bedroom 2

1 Queen Bed and 1 Double Bed

Guest bedroom w/add’l room

1 Double Futon, 1 Queen Bed, 1 Single Bed and 1 Crib

Master

1 King Bed

3 bathrooms, 1 half bathroom

Basement

Bathtub or shower · Toilet

Guest bath

Bathtub or shower · Toilet

Master bathroom

Toilet · Shower only · Jetted bathtub

Powder

Toilet

Spaces

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

About this property

Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”

Farmhouse meets beach house at “The Vacation House”…beautiful North Fork Farm House in relaxing farm/beach area perfect for families who want a truly relaxing atmosphere.

Home comes with front patio (great for morning coffee!), 4 Bedrooms (can sleep 10-12 people depending on your needs) plus additional bunk beds in the basement with a bonus guest room. Bonus room has a pullout couch, pack n’play (if needed) and chaise lounger. The basement also bunk beds, a couch, private full bathroom and bar. The Basement has a full bar area, pop a shot, ping pong (2023 addition), foosball, 70” TV. Sliding Glass Doors Lead to the Outside Patio Entertaining Space with outdoor dining, outdoor couch/egg chair, updated outdoor kitchen with BBQ (2025) 2 Pergola areas (with new outdoor TV), fire pit, hammock and Pool (pool heater installed 2021, full pool remodel 2023) with lounge chairs and umbrellas (pool shed for storing floats and toys). There is a large yard with climbing gym, soccer goal and cornhole set/other games. Heated floors in the kitchen and master bathroom help in the winter months along with working fireplace.

In 2023, the owners have installed an outdoor shower and hot tub area adjacent to the back deck!

For fitness, this home has a converted three car Detached Garage converted to a gym and equipped with oversized workout mats, yoga mats, full set of weights, infrared sauna, peloton bike, boxing bag, indoor basketball hoop, additional workout equipment and a trampoline for kids. There is an attached two Car Garage for storage of bikes and beach accessories with direct entry access to the kitchen to come and go. The house had some renovations done by the new owners in 2021 - updated bathrooms, better WiFi, increased streaming services added for TV viewing, updated basement and fresh paint across entire home.

Great location close to nearby town (7 mins), farm stands, town beaches and public beaches, Parks, Orient Point State Park, Greenport (10-12 mins) and many wineries and restaurants.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Must take all garbage and recyclables to the Southold Town dump prior to leaving (Yellow Town garbage backs are provided/ Cox Lane location)
Prior to leaving: Turn both A/C units (nest thermostats) to 76 degrees in summer / turn down to 65 in winter / turn pool temperature to 75 degrees
Return all furniture to original positions

Important information

You need to know

Property # 2317113vb
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
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 and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Southold

Located in Southold, this holiday home is in a rural area and near a water park. Greenport Carousel and Camera Obscura are local landmarks, and some of the area's activities can be experienced at Croteaux Vineyards and Osprey's Dominion. Travelling with kids? Consider Custer Institute and Observatory and 8 Hands Farm. Discover the area's water adventures with power boating, fishing and swimming nearby, or enjoy the great outdoors with hiking.
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Map
Southold, NY

What's nearby

  • Custer Institute and Observatory - 4 min drive - 3.9 km
  • Croteaux Vineyards - 4 min drive - 3.5 km
  • Sparkling Pointe - 6 min drive - 5.6 km
  • Raphael Winery - 7 min drive - 7.8 km
  • Pindar Vineyards - 7 min drive - 8.1 km

Getting around

  • Southold Station - 6 min drive
  • East Hampton, NY (HTO) - 78 min drive

Restaurants

  • ‪Dunkin' - ‬6 min drive
  • ‪Sophie's Rest - ‬4 min drive
  • ‪Pridwin Hotel - ‬38 min drive
  • ‪Panoramica - ‬7 min drive
  • ‪North Fork Roasting Co. - ‬7 min drive

Frequently asked questions

Does Beautiful updated home with pool by Wineries and Beaches - “The Vacation House” have a pool?

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

Is Beautiful updated home with pool by Wineries and Beaches - “The Vacation House” pet-friendly?

No, pets are not allowed at this property.

How much is parking at Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”?

On-site parking is available at the property.

What time is check-in at Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”?

Check-in begins at 4:00 PM.

What time is check-out at Beautiful updated home with pool by Wineries and Beaches - “The Vacation House”?

Checkout is at 11:00 AM.

Where is Beautiful updated home with pool by Wineries and Beaches - “The Vacation House” located?

This family-friendly Southold holiday home is located in a rural location, within 3 mi (5 km) of Croteaux Vineyards, Custer Institute and Observatory and Osprey's Dominion. McCabe's Beach and Goldsmith's Inlet Park are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Family trip

The house was beautiful. Everything was perfect and so easy. Thanks for a wonderful stay
Stayed 2 nights in Nov 2021
Response from VrboOwner on 6 July 2023
Thanks for the review and taking such good care of the house! Hope you can join us again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Owner gets back immediately with any questions.Beautiful home. Perfect for family get togethers!
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

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

Summer fun!

A great time was had by all. So many nice amenities.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 6 July 2023
It was great to have you and your family at our house. We are very happy you enjoyed your stay.
Verified review

10/10 Excellent

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

Such a special place

The house has all of the touches of a family home. The beds were extremely comfortable and the house was very clean. The basement is a dream for kids - all of that said, our favorite space was the backyard… the adults spent every night by the outdoor seating area with the TV and the kids couldn’t get enough of the pool and soccer net. All around a great stay!!
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Perfect getaway from NYC

We loved our stay at the property. Super clean, very spacious, great outdoor area for adults to grill and enjoy the gazebo by the pool with a huge lawn/ soccer field for kids to run while not at the pool. The hosts were a pleasure to work with with fast responses and well organized manuals, and went out of their way to make our stay enjoyable. Definitely coming back.
Stayed 7 nights in Jun 2021
Response from VrboOwner on 6 July 2023
Thanks for the kind review, we look forward for hosting you again!
Verified review

10/10 Excellent

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

The perfect house for everyone!

This house has it all. Heated floors, entertainment for kids, convenient location to farms, water, and vineyards, comfortable beds and more. I can not wait rent again!
Stayed 2 nights in Dec 2021
Response from VrboOwner on 6 July 2023
It was wonderful to have a great family in our home. Thank you for the kind review and look forward to having you again.
Verified review

10/10 Excellent

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

Fun and relaxing retreat

Beautiful home and property with so much to do. We enjoyed the house so much, we ended up relaxing and swimming in the pool every day instead of trekking around to find things to keep us occupied. We felt like we had our own private oasis and only left to go to dinner at some of the restaurants. Quiet neighborhood with quick access to the town, Greenport, the wineries and shopping. Owner was super responsive and helpful. We wish we stayed longer!
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Could not have been better!! Huge home, huge pool, huge backyard!!! Pool floats there for the heated pool, great hot tub. If you like grilling, welcome to nirvana. Bikes available to ride to the beach or just around the neighborhood. Owner is super responsive. Peaceful, quiet. Sad to leave! If you have kids, the basement has a basketball game, ping pong table and big screen TV. I’m an adult and I loved it!!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

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

Beautiful Home / Relaxing Stay!!

We stayed for almost two weeks in August. We LOVED this property and would definitely stay here again. Communication with the host was great (e.g. helpful tips, detailed instructions, etc.). What we liked: *The house is comfortable and very clean. *The pool is awesome. Backyard is huge with a cabana, grill, fire pit and even a soccer goal!! *Lots to entertain kids inside: Nok hockey, basketball arcade, foosball, board games, puzzles, books, etc. *Separate office space and good connectivity if you need to get a little work done. *Separate gym with basic weights and peloton. *Great location: quiet/safe neighborhood, less than a five minute drive to Southold village, close to vineyards/beaches There are too many good things to name them all. You can't go wrong staying here!!
Stayed 11 nights in Aug 2022
Verified review

10/10 Excellent

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

Great Family Vacation

My family and I stayed at the property for 7 days during a heat wave! The house was as nice as advertised. The pool was beautiful and refreshing throughout the heat wave. Home was well stocked with paper goods soap, etc. House was cleaned up and spotless prior to our arrival.Communication with the property owner was excellent. Definitely a 5 star review!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Great girls weekend!

The house was idyllic. We love the farmhouse meets beach decor (and the heated kitchen floors!). The bedrooms were perfect — out biggest regret was not soaking in the tub in the master bedroom. Our only watch out is the hot water: you’ll want to stagger your showers if you’re a large group. The shared spaces are great for entertaining or just relaxing between excursions. Between the basketball in the basement and the trampoline in the garage/gym, we felt like kids in the movie Blank Check. (TLDR; classic 90s kid film and a must watch). We can’t wait to come back in the summer, when the pool is open!
Stayed 2 nights in Feb 2022
Response from VrboOwner on 6 July 2023
Thanks for staying at our home - we welcome you back when you can use the pool!
Verified review

10/10 Excellent

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

Cozy Family Stay

We stayed after Christmas and through New Years and had a wonderful time. My 3 and 5 year old found plenty to keep themselves occupied with the toys, trampoline, and finished basement. The adults enjoyed the fireplace, reading nook, and playing basketball with the kids. While we were there in the off-season we found plenty to do, and Leor gave us all the good spots to hit up. We can't wait to go back when the pool is open!
Stayed 5 nights in Dec 2021
Verified review

10/10 Excellent

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

Great stay

This was the perfect property for a relaxing weekend away for myself and a small group of friends. The house is beautiful and Leor was quick with all his responses!
Stayed 3 nights in Oct 2021
Response from VrboOwner on 6 July 2023
Thank you! Happy you enjoyed your stay.
Verified review

10/10 Excellent

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

Easy family getaway

We had a wonderful stay here at the end of July. Host was super responsive and answered all my questions almost immediately. The house is in a great spot. Easy access to Orient Point, Greenport, vineyards and farms. Our kids fully enjoyed the pool, basketball court in the detached garage, and the rec room in the basement. Everything we could have asked for and more in this house. Definitely made this one of the easiest and relaxing stays away from home.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 6 July 2023
Thank you for the review, it was wonderful to have you and your family at our home!

About the host

Hosted by Leor Shapiro

Host profile image
Owners are a family of four (with a 10 year old boy and 7 year old girl) who purchased the house in January 2021. The family wanted to make this a true "home" for families to enjoy for years to come and fell in love with the local area, farms (and wineries) that make it feel very special, private and a great place to create memories.

Why they chose this property

Relax by the oversized pool, sit by the fire pit, enjoy all the local wineries (within 5-10 mins from the house), be near all the farms (goats, horses, sheep, chickens) and all the local beaches and trails. It's a very special and relaxing location from sunrise on the front porch to sunset over then backyard.

What makes this property unique

Purchases, updated and furnished in early 2021, detached garage converted into a full gym with sauna/peloton/weights/bands/kids trampoline etc, large backyard for running and playing, updated bathrooms, basement entertainment with pop a shot, nok hockey, kids plays area, new 70" TV, fooseball/plastic dart board areas and much much more. Backyard has outdoor TV, hot tub, outdoor shower, couches on the deck and pergola seating area.

Languages:

English
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