Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Photo gallery for Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

An outdoor deck with wicker furniture, a round table, and a wooden deck.
A modern living room with a sofa, coffee table, and a TV mounted on the wall.
A room with a brick wall, a star decoration, a bench, a white cabinet with shelves, and a small table.
A garage with two bicycles parked inside.
A modern living room with a flat-screen TV mounted above a fireplace, a comfortable seating area with a bench, and a large potted plant.

Reviews

10 out of 10
Exceptional

Highlights

  • Top-rated for value
    Guests love how much they get for what they pay.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Dog-friendly
  • Toys
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

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

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Queen Bed

Master Bedroom

1 King Bed

2 bathrooms

Guest Bathroom

Bathtub or shower · Toilet

Master Bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Separate dining area
Garden
Dining area

Add dates for prices

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About the area

Southold

Southold is home to this holiday home. The area's natural beauty can be seen at The Hamptons Beaches and Cooper's Beach. Travelling with kids? Consider Custer Institute and Observatory and 8 Hands Farm.
View more Holiday homes in SoutholdOpens in a new window
Map
Southold, NY

What's nearby

  • Croteaux Vineyards - 3 min drive - 2.5 km
  • Custer Institute and Observatory - 3 min drive - 2.5 km
  • Sparkling Pointe - 5 min drive - 4.9 km
  • Raphael Winery - 6 min drive - 6.7 km
  • Pindar Vineyards - 7 min drive - 7.1 km

Getting around

  • Southold Station - 6 min drive
  • East Hampton, NY (HTO) - 81 min drive

Restaurants

  • ‪Dunkin' - ‬6 min drive
  • ‪Pridwin Hotel - ‬38 min drive
  • ‪North Fork Roasting Co. - ‬6 min drive
  • ‪Michelangelo's - ‬6 min drive
  • ‪Panoramica - ‬6 min drive

Frequently asked questions

Is Family and dog-friendly getaway near amazing wineries, beaches and restaurants! pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Family and dog-friendly getaway near amazing wineries, beaches and restaurants!?

As of 13 Nov 2026, prices found for a 1-night stay for 2 adults at Family and dog-friendly getaway near amazing wineries, beaches and restaurants! on 14 Nov 2026 start from AU$4,457, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Family and dog-friendly getaway near amazing wineries, beaches and restaurants!?

On-site parking is available at the property.

What time is check-in at Family and dog-friendly getaway near amazing wineries, beaches and restaurants!?

Check-in begins at 4:00 PM.

What time is check-out at Family and dog-friendly getaway near amazing wineries, beaches and restaurants!?

Checkout is at 10:00 AM.

Where is Family and dog-friendly getaway near amazing wineries, beaches and restaurants! located?

This family-friendly Southold holiday home is within 2 mi (3 km) of Croteaux Vineyards and Custer Institute and Observatory. Osprey's Dominion and Sparkling Pointe 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.
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Rating 10 - Excellent. 42 out of 42 reviews
Rating 8 - Good. 0 out of 42 reviews
Rating 6 - Okay. 0 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 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

Perfect Family Vacation Getaway

Location, hosts, house - everything was great! Can’t wait to go back!
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

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

Family Wedding

Stayed for family wedding - great location, great house, great host. Could not have asked for anything better!!!
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely beautiful accommodations. Great flow within the home. Generous toiletries, towels and beddings. Close to wineries, yacht club, shopping. Samantha was a pleasure and answered my questions quickly. Would recommend this home for all Thank you for allowing us to stay
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

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

Summer vaca

Place is clean and bright. The house is equipped with everything we need. Had a perfect stay with 3 boys. Perfect location to vineyards and water park.
Stayed 5 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a beautiful clean home and my family and I enjoyed it thoroughly
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

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

Beautiful fall north fork weekend

We had the best time visiting Sam & Matt’s place in Southold. The house is the perfect size for us- 3 adults and 3 kids plus 2 dogs. And it was an ideal location to explore all the north fork has to offer. We can’t wait to return!
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

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

The Best

Beautiful home - comfortable and so clean. We had a beautiful stay. Host answered all our questions promptly. Location was great. Fantastic time. Thanks so much.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

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

Perfect

The house was perfect for the family and had everything we needed. We will be back!
Stayed 3 nights in Apr 2023
Verified review

10/10 Excellent

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

Great location!

We would recommend this property. Good location, quite cul de sac, private backyard. Comfortable home. New kitchen and appliances. Good AC and heat. Convenient to vineyards, beaches, shopping. All around great location.
Stayed 5 nights in Apr 2023
Verified review

10/10 Excellent

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

Delightful home

Everything was great. The house is in a lovely, quiet neighborhood. It is spotlessly clean and very well-appointed, with everything we needed for a fun and comfortable stay. Sam was very responsive and even left us a bottle of delicious rose wine from a local vineyard. We would recommend this home without reservation. LN from CT
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

Beautiful Home

This home was perfect for our family. It's clear the home is a home that is well cared for and loved. Clean, beautifully decorated, well equipped... we travel with pots, pans, seasonings, etc Bavaria many rentals are bare bones even when they are well staged/decorated. This home had almost everything we needed to cook. My family all expressed how comfortable theirs rooms and beds were and how well they slept. It's a bit of a way from our tribal territory but it's well worth the drive.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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

Best location, Best property, BEST vacation!

I could not be happier with our choice. This home was perfect from start to finish. The kitchen was well equipped, the amenities ( beach gear, bikes, cooler, chairs,etc) were absolutely key, the beds were so comfortable, the bathrooms were stunning. Such a great value for me and my 6 friends! Southhold and Greenport had so many amazing places and things to do. I wish we could stay for a a few weeks. It's so hard to choose the right place for your vacation- but don't hesitate. I will be recommending this home to my friends and family. Feeling so blessed after an unforgettable weekend.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

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

Wonderful, peaceful escape

Visited for a family wedding with my mother, husband and three kids (6, 4, 6mo) and had a lovely stay. The house was exactly as expected and worked out great for all of our needs.
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Always the best stay!

We loved staying here for the second time. The house is always spotless and in a great location. Sam is always responsive and available to help. We will be back again for sure!
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Best Place Ever

I spent three weeks at this wonderful place with my son, daughter-in-law and two grandchildren (3 and 6) and a small dog and everyone was thrilled with the accommodations. The place is beautifully furnished, but not too chi-chi to make more than a little child-proofing necessary. The location is near town and several terrific beaches but in a quiet cul-de-sac so 6 year old could practice riding his bike. Not only was there a large TV with access to Disney channel plus adult viewing, but the garage was outfitted with lots of games and equipment. The most comfortable beds I've slept on in years but terrific AC and very responsive property manager.
Stayed 21 nights in Aug 2022
Verified review

10/10 Excellent

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

Great Trip!

Wonderful clean house, great location and great communication with the manager/owners. We very much hope to be back!
Stayed 14 nights in Jul 2022
Verified review

10/10 Excellent

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

Amazing House

Hosts were very easy to communicate with and graciously accommodated a date change we had for the trip. The house was gorgeous and location was great. Definitely coming back!
Stayed 3 nights in Jul 2022
Verified review

10/10 Excellent

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

Just Perfect

We were immediately impressed with how neat and beautiful the home was. We knew it was going to be nice, but everything exceeded our expectations. We were two couples with a small dog, and had plenty of space both indoor and outdoor to enjoy. The bikes were an amazing plus for us, as the weather wasn't yet too hot for spending the day at the nearby beaches, so we definitely rode around the beautiful neighborhood quite a bit. House appeared to be recently renovated with all new appliances - everything was working perfectly and we had absolutely no issue. Important to note that one of the bathroom is across the house, but even that was not an issue, as they were all so spacious and master bathroom had two doors (one to bedroom and one to hallway). We were not familiar with the area, but there were soo many wineries and great restaurants in nearby cities. We will definitely be coming back! Sam and Matt were super responsive, and fulfilled every ask we had.
Stayed 3 nights in Jun 2022
Verified review

10/10 Excellent

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

Relaxing MDW

Host very responsive! House nicely provisioned and very comfortable. We loved it.
Stayed 3 nights in May 2022
Verified review

10/10 Excellent

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

Amazing house!!!

Great experience with my family, would definitely recommend.
Stayed 4 nights in Nov 2021
Verified review

10/10 Excellent

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

Amazing home and Perfect Hosts

The pictures don't do Sam and Matt's home justice. The house is amazing and they were super responsive and great communication. I would definitely rent from them again.
Stayed 3 nights in Sep 2021
Verified review

10/10 Excellent

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

Beautiful home, as advertised

CLEAN and modern, lovely home for a nice getaway. Great location. Great communication w owners. Would definitely rent again!
Stayed 4 nights in Aug 2021
Verified review

10/10 Excellent

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

North Fork vacation

Great place!
Stayed 14 nights in Aug 2021
Verified review

10/10 Excellent

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

Lovely house, great location

We loved our stay here. The house is comfortable and stylish, with a well-equipped kitchen and a deck with a dining table and chairs, which we used most evenings. There was plenty of room for six adults. Easy access to shops in Southold and we enjoyed the one mile walk to a pretty beach. With a helpful list of wineries and restaurants, games, bikes and beach towels, the owners thought of everything that would make for a perfect visit. We would happily return.
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

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

Winter wonderland & Perfect family holiday stay

We were lucky enough to stay at this beautiful house right after a snowstorm so both the house and the town of Southold looked like it was right out of a fairy tale. The pictures of the house don’t do it justice- beautifully decorated in a modern, comfy style. Someone in our group commented on the amazing cleaning service since it was so spotless. The layout of the house was both spacious and intimate-perfect for our family. For those that are hesitant to visit the North Fork in the winter-there are still so many stores, restaurants and wineries open for enjoyment. Sam and Matt were gracious and responsive hosts. We hope to be able to stay again soon!
Stayed 8 nights in Dec 2020
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