Southold Escape with Large Saltwater Pool on Wine Trail

Photo gallery for Southold Escape with Large Saltwater Pool on Wine Trail

A dining area with a wooden table and chairs, a chandelier, and a sign that reads "SOUTHOLD" on the wall.
A living room with a blue sofa, a striped rug, a white throw blanket, and a framed picture on the wall.
A swimming pool with a wooden deck and a fence.
A living room with a blue sofa, wooden flooring, a dining area with a table and chairs, and a window providing natural light.
A room with a large sliding glass door leading to an outdoor patio area with a pool, seating, and a fenced garden.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.

Popular amenities

  • Patio
  • Private pool
  • On-site fitness centre
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Southold, NY
  • Place, Hashamomuck Pond
    ‪13 min walk‬
  • Place, The Old Field Vineyards
    ‪2 min drive‬
  • Place, The Hamptons Beaches
    ‪41 min drive‬
  • Airport, New London, CT (GON-Groton - New London)
    ‪146 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden

Add dates for prices

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About the area

Southold

Located in Southold, this holiday home is near the beach. Custer Institute and Observatory and Greenport Carousel are local attractions and those in the mood for shopping can visit Greenport Farmers' Market and Love Lane. Railroad Museum of Long Island and East End Seaport Maritime Museum are also worth visiting.
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Map
Southold, NY

What's nearby

  • Hashamomuck Pond - 13 min walk - 1.1 km
  • The Old Field Vineyards - 2 min drive - 2.2 km
  • Raphael Winery - 7 min drive - 8.1 km
  • The Hamptons Beaches - 41 min drive - 51.0 km
  • Cooper's Beach - 56 min drive - 63.3 km

Getting around

  • Southold Station - 17 min walk
  • East Hampton, NY (HTO) - 75 min drive

Restaurants

  • ‪Dunkin' - ‬2 min drive
  • ‪Sophie's Rest - ‬4 min drive
  • ‪Pridwin Hotel - ‬32 min drive
  • ‪Panoramica - ‬4 min drive
  • ‪North Fork Roasting Co. - ‬14 min walk

Frequently asked questions

Does Southold Escape with Large Saltwater Pool on Wine Trail have a pool?

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

Is Southold Escape with Large Saltwater Pool on Wine Trail pet-friendly?

No, pets are not allowed at this property.

How much is parking at Southold Escape with Large Saltwater Pool on Wine Trail?

On-site parking is available at the property.

What time is check-in at Southold Escape with Large Saltwater Pool on Wine Trail?

Check-in begins at 4:00 PM.

What time is check-out at Southold Escape with Large Saltwater Pool on Wine Trail?

Checkout is at 11:00 AM.

Where is Southold Escape with Large Saltwater Pool on Wine Trail located?

Situated near the beach, this holiday home is 1.1 mi (1.7 km) from The Old Field Vineyards and within 3 miles (5 km) of Sparkling Pointe and Horton Point Park. Custer Institute and Observatory and Horton Lane Beach are also within 3 miles (5 km). Southold Station is 17 minutes by foot.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 11 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 1 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 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
We had a great trip, and Athena was very welcoming and easy to work with.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was clean and the backyard and pool were perfect. Great location and responsive hosts.
Stayed 4 nights in Aug 2026
Response from VrboOwner on 16 August 2026
Thank you Rob! You guys were great and are welcome back anytime!
Verified review

10/10 Excellent

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

We enjoyed very much our stay. House, terrasse , garden and pool were perfect for all the Family!

Best location to visit grève port it go to shelter island
Stayed 3 nights in Sep 2022
Response from VrboOwner on 13 September 2023
It was lovely to host you and we were so happy to have such wonderful guests. You left the house spotless and we appreciate it. Come back and visit anytime.
Verified review

10/10 Excellent

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

Our stay

The home was very cozy! Host was easy to communicate with and made us feel welcome. Would stay here again!
Stayed 1 night in Apr 2023
Verified review

10/10 Excellent

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

Girls weekend

We had the best time this weekend. The house is beautiful, the communication between the owners is great and there is so much around the area!
Stayed 2 nights in Jun 2022
Response from VrboOwner on 13 September 2023
Thank you Meghan. You were wonderful guests. Come back anytime.
Verified review

10/10 Excellent

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

Great time!

Beautiful house, well equipped. Thanks again!
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

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

Wedding

Enjoyed
Stayed 2 nights in May 2023
Verified review

10/10 Excellent

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

Awesome Girls Weekend trip

The property was very homely. The place was spotless. Our host was very easy to get hold of and made sure we had the best experience. She gave detailed instructions so when we needed something, we knew exactly what to do. Will definitely come back again. Location was perfect as it was close to the water and the wineries. The patio was a great place for a bbq and we used the fire pit to make s’mores.
Stayed 2 nights in Jul 2022
Response from VrboOwner on 13 September 2023
Thank you for the kind words Rubi! You guys were great!
Verified review

10/10 Excellent

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

Perfect northfork getaway!

What a perfect northfork getaway! The house is in the perfect location, close to towns, vineyard, and plenty of restaurants. The house was immaculate, and very comfortable. It was stocked with all the necessities for us to cook great meals, and cleaning supplies. Backyard was perfect for hanging out, and the pool is beautiful (and fenced making it very safe). The property is big and great for families. Athena was SO great to work with, and easy to get in touch with for any questions we had. She made sure we were comfortable traveling with our infant, and made the house very accommodating! We already can’t wait to return!
Stayed 2 nights in Jul 2022
Response from VrboOwner on 13 September 2023
thank you so much for the kind words. You and your family were a pleasure to have. We can’t wait to host you and your lovely family again!
Verified review

10/10 Excellent

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

Another great stay!

Our second stay was just as great as our first! Athena and her husband are amazing hosts, and we're easy to reach the whole weekend. They were extremely flexible with check in and check out times, which was very much appreciated. The house was clean and stocked with everything we could possibly need, even equipment for my infant. We cooked a great meal in the kitchen, and the yard was comfortable for a cozy glass of wine. The location of the house couldn't be better, so close to stores and vineyards. We can't wait for our next stay!
Stayed 1 night in Oct 2022
Verified review

6/10 Okay

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

We'll be back next year!

Absolutely amazing week at 155 Oriole. We arrived to a spotless, well-stocked home with tons of towels, high end kitchenware and everything we needed (next year I can pack a lot less!) The pool and deck were fabulous and even though we sometimes didn't want to leave, the location was incredible. Less than a five minute drive to the charming town of Southold with a great butcher shop (Wayside Market), bakery (Blue Duck), IGA and a wonderful farmstand and fish market down the road. Convenient to everything...Mattituck is a ten minute ride and wineries are everywhere (our favorite was the beautiful Croteaux). Check-in was super simple and stressfree and the host answered any questions we had. There were four adults for the week - one working from home - and we never got in each others' way. Our niece and nephew stopped by one day with their 10 month old...the house is even child friendly (and the LI Aquarium is only a 30 minute drive) Overall, our experience far surpassed our expectations and we can't wait to come back!
Stayed 6 nights in Aug 2022
Verified review

10/10 Excellent

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

Great time in wine country!

This is a lovely house in a great location. The pool was super clutch during a historic heat wave and we were just a short drive from Greenport and the vineyards. The house is bigger than it looks in the photos -- the yard in particular is huge -- and our group of 6 had plenty of space, and is well stocked with everything you'd need (including excellent AC). Can't recommend enough!
Stayed 2 nights in Jul 2022
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