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Kenneys Beach retreat by the Wineries

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Living area
Living area
Living area
Interior
Private kitchen

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 101600 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Outdoor space

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

2 Double Beds

Bedroom 2

2 Single Beds and 1 King Bed

Bedroom 3

2 Double Beds

2 bathrooms

Bathroom 1

Bathtub · Toilet

Bathroom 2

Bathtub · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden

About this property

Kenneys Beach retreat by the Wineries

This 3 bedroom 2 bathroom Ranch with open floor plan is just a short distance to one of the nicest and sandiest beaches on the North Fork with the most amazing sunsets you have ever seen! The North Fork is famous for its Wineries and this home puts you in the middle of them all. Close to all amenities such as supermarkets, restaurants, bars, cafes, pharmacies etc. Lounge out on the huge 16 x 42 deck after walking back from beautiful Kenneys Beach.
Recently fully renovated, the home boasts 3 spacious bedrooms. One bedroom has a King size bed and 2 twins. The other 2 bedrooms have 2 full size beds each. The home comfortably sleeps 6 adults and 4 children and has Wifi , smart TV, Central A/C and a very comfortable Living room with Cathedral ceilings. Don't miss out on the perfect family get away.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 3–17
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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
EVERY INQUIRY MUST BE SUPPORTED BY SOME TYPE OF GOVERNMENT ISSUED ID. This is to protect all parties involved in the transaction.
If any pets are found on the property there will be a $500 pet cleaning fee charged.We reserve the right to inspect for damages incurred by pet(s).

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
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 deadlock

About the area

Southold

Located in Southold, this holiday home is near a water park and near the beach. Sparkling Pointe and Croteaux Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore The Hamptons Beaches and Hallock State Park Preserve. 8 Hands Farm and Railroad Museum of Long Island are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and hiking.
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Map
Southold, NY

What's nearby

  • Sparkling Pointe - 13 min walk - 1.1 km
  • Horton Lane Beach - 14 min walk - 1.2 km
  • McCabe's Beach - 2 min drive - 1.8 km
  • Custer Institute and Observatory - 3 min drive - 2.5 km
  • Shelter Island - 32 min drive - 15.1 km

Getting around

  • Southold Station - 6 min drive
  • East Hampton, NY (HTO) - 79 min drive

Restaurants

  • ‪Dunkin' - ‬4 min drive
  • ‪Michelangelo's - ‬4 min drive
  • ‪North Fork Roasting Co. - ‬5 min drive
  • ‪Southold General - ‬4 min drive
  • ‪Sophie's Rest - ‬4 min drive

Frequently asked questions

Is Kenneys Beach retreat by the Wineries pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Kenneys Beach retreat by the Wineries?

As of 3 Apr, 2026, prices found for a 1-night stay for 2 adults at Kenneys Beach retreat by the Wineries on 1 Dec, 2025 start from S$808, 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 Kenneys Beach retreat by the Wineries?

On-site parking is available at the property.

What time is check-in at Kenneys Beach retreat by the Wineries?

Check-in begins at 4:00 PM.

What time is check-out at Kenneys Beach retreat by the Wineries?

Checkout is at 11:00 AM.

Where is Kenneys Beach retreat by the Wineries located?

Situated near the beach, this holiday home is 0.6 mi (1 km) from Horton Lane Beach and within 3 miles (5 km) of Sparkling Pointe and Goldsmith's Inlet Park. Sannino's Bella Vita Vineyard and Mattebella Vineyards are also within 3 miles (5 km).

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. 30 out of 35 reviews
Rating 8 - Good. 5 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Julie C.

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

Wonderful stay

It was a wonderful stay! We would love to come back!
Stayed 2 nights in Nov 2023
Verified

8/10 Good

Kevin J.

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

Great home for a family renunion

VRBO made it easy to find the right place for what we needed
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Patricia C.

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

Girls Trip

Nice accommodations! Perfect for our getaway!
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

ed t.

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

Family reunion

Great house great property very comfortable I would highly recommend
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Suzanne D.

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

Updated home

Comfortable beds and kitchen has all the bells and whistles. Great location for us. Hope to be back.
Stayed 3 nights in Dec 2021
Verified

10/10 Excellent

David A.

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

Wonderful Beach House~

This is the second year we have stayed ay Kenny's Beach retreat and we will absolutely be back! Charming, open concept house, fits everyone easily, walking distance to the beach and a short car ride to restaurants, wineries or into downtown Greenport. Thanks so much!
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Jose L.

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

Great Retreat!

It is an impressive property...tucked away in a quiet wooded area, surrounded by awesome wineries, and a short, relaxing walk to the beach. We booked the house for 3-days/2-nights and time just flew by. We would definitely return and stay longer, for sure!
Stayed 2 nights in Jul 2022
Verified

10/10 Excellent

Melissa K.

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

Great location on North Fork

Very comfortable for two couples. Rob very responsive.
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Elizabeth Lambos t.

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

Great place, beautiful area close to beach

We had a lovely time. The property had a great kitchen and outside grill/patio which was perfect for cooking for a group. We had six adults and two small kids and everyone was comfortable. It is a scenic 10 min walk to Kennedy’s beach and the area is also nice and shaded for going for walks/runs. Would love to stay again.
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Jessica R.

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

Girls Weekend

Great location, close to the beach & wineries. House was nice & clean. My friends and I enjoyed the house. Thank you !
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Kerry T.

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

Great Beach Retreat

We needed an overflow place for my many nieces, nephews and our family. Having multiple beds and bathrooms were key. We enjoyed coming back to a nice clean and air conditioned house after a long day out and about. It was perfect!
Stayed 3 nights in Jul 2023
Verified

8/10 Good

Georgeann C.

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

Nice House

This house is a perfect setup for 2 couples or 2 families. It is a great location and close to hiking trails and the beach. There is only a keurig, so if you like coffee bring a French Press!
Stayed 5 nights in Dec 2022
Verified

10/10 Excellent

Sabina S.

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

Ocean sound

We are returning costumes, we were at the house exactly last year, and again nothing disappointed us. My friend and all the kids had a blast, beach was just a walking distance, house was perfect and cozy. That really was a great vacation.
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Brian W.

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

Great house in North Fork

This is a great house for a stay in the North Fork. Very accessible to everything. Bedrooms and bathrooms are more than enough, nice open kitchen living space. Property managers were very communicative and helpful. Easy check in and out. Highly recommend!
Stayed 2 nights in Oct 2021
Verified

10/10 Excellent

Emily A.

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

Family Stay

This home is exactly as depicted. The layout is perfect if your looking to fill your home with a large family. It was perfect for everyone from my two year old son to my 67 year of step father. Large yard and about a mile from the beach. Overall perfect.
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Sabina S.

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

Perfect getaway

It was perfect getaway with friends and my daughters. The house was more than perfect, the location the rooms the space. Every day beautiful sunset at the beach. I definitely saved the house for future vacation. The house manager was very nice, very helpful and easy to communicate with. I miss this place already.
Stayed 3 nights in Jul 2022
Verified

8/10 Good

Virginia D.

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

Kenny’s Beach Retreat

The interior of the property is as advertised, updated and with beds and bedding very comfortable and kitchen adequately stocked. The host was very nice and helpful. Exterior needs work and not very inviting. Nice deck, which was important to us, but needs better cleaning and some landscaping. Convenient access to beaches. Overall good stay.
Stayed 3 nights in Aug 2023
Verified

8/10 Good

Virginia S.

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

Wedding weekend

The house was perfect for 3 couples in town for a wedding & party the next day. The kitchen faucet needs some work. It would be nice to have directions on how to work the TV. The house worked out great for our wedding weekend. Great location.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Evan F.

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

A good staty

The property was very nice. The bedrooms and baths were good. The kitchen and large living area was just what we needed. The only criticism is tv in the main bedroom was not hooked up to anything. Not sure why they would have a tv with no input.
Stayed 3 nights in Sep 2022
Verified

10/10 Excellent

donna b.

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

girls weekend

property was perfect for 6 women on a girls weekend. there were 6 of us for 4 days and there was a shortage of towels for showering. we wanted to do a wash but the machine did not work as well as the drier. other than that, we had a great stay. great location, beautiful grounds, lovely home.
Stayed 3 nights in Apr 2023
Verified

8/10 Good

Mike I.

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

Family trip

Great location between Greenport and most of the wineries. House looks great, wonderful value. A few things that are typical of most vrbos are true here too. Kitchen utensils, beds and couches aren’t great. I couldn’t find a knife (or sharpener) that would cut a tomato. Beds and bedding feel like plastic, very squeaky. New couch needed. Yard is great, you’ll see rabbit and deer. Walk to the beach and little fish restaurant. Everything else about 10 minutes drive.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Erika V.

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

Nice house

Big property with a nice deck outback to hangout with family. We stayed for a family reunion so it was nice to have a place for everyone to meet up and be able to hangout without feeling on top of each other. A short walk to the beach and a nice restaurant right down the street. Be aware it is a walk to the beach so ask in advance for a pass for your car so you can park at the lot in front of beach. A detail i must have missed. It was a bit of a hassle to do car loads of drop offs and then park back at the house and walk. Also not ideal to have to walk with young kids as there are no side walks I saw a lot of comments about kitchen and not being stocked. Seemed to be adequately stocked for having to cooks meals and enough dish ware. TVs we’re a little confusing to work and not sure the master bedroom one worked. Looks like the property owners are doing some work on that though. The only thing about the house that was terrible were the beds. I’m usually able to hack sleeping on a bad bed if it’s only a couple of night but these beds were beyond bad so noisy and felt like sleeping on rocks.
Stayed 4 nights in Aug 2023
Verified

10/10 Excellent

Nicholas P.

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

Great space, great location

Minutes walk from the beach and snug in the woods, this was the perfect retreat for our New York Thanksgiving. Kitchen was huge, with new appliances and plentiful counterspace. Sleeps as many as you have, comfortably, and will seat (almost) that many in the living room and at the kitchen table. Really the perfect space for just about anything. Only minor cleanliness issues (toilets and shower curtains could've used some more TLC). Would stay here again without hesitation.
Stayed 3 nights in Nov 2022
Verified

10/10 Excellent

Bryan S.

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

Enjoyable experience

We had a great weekend at the home. It was inviting and well maintained. The owners were easy to communicate with. My kids loves the size of the property and had a great time running around exploring. We will definitely be booking again next year!
Stayed 3 nights in Oct 2022
Verified

10/10 Excellent

Mary C.

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

Peconic wedding.

This property was worked out wonderfully for us. We were out for a wedding at a local venue. Even though the weekend wasn't the nicest weather the house was bright and had all the amenities we needed. This was a great location for our party of 4 adults. Close to wineries and local restaurant's. Highly recommend if looking for a relaxing weekend with friends.
Stayed 2 nights in Sep 2022

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