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Featured Cottages in North Fork

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (25)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Northfork Ranch Style Cottage walking distance to beach & Wineries

Northfork Ranch Style Cottage walking distance to beach & Wineries

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (17)
"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."
Walk to Love Lane! Immaculately renovated private cottage.

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (27)
"This is great property - perfectly renovated and close to everything including a nice North Fork beach in walking distance. Our host Bill communicates well and has thought of everything - house is well appointed and tastefully renovated with AirCon and washer/dryer. Sheets and Towels are clean and high quality! A beautiful, lush and grassy yard awaits your kids and the fire pit is perfect. Bill, our host was very nice in providing suggestions on where to go and what to do - some very nice...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (22)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
Orient Village — Historic Bayfront Cottage — 2025 Season

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (176)
"Excellent"
Fabulous Waterfront Property in the Heart of Wine Country

Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

9.8 out of 10, Exceptional, (10)
"What a great little get away weekend in a beautiful cottage in the middle of wine country. Great host a lovely accommodations"
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

Walk to Breakwater Beach in Heart of Wine Country

9.8 out of 10, Exceptional, (12)
"Lovely place to stay beautiful location. Carl was super responsive and accommodating. Thank you!"
Walk to Breakwater Beach in Heart of Wine Country

Classy Getaway w/ Deck & Yard < 1 Mi to Beach

3.0 star property
Classy Getaway w/ Deck & Yard < 1 Mi to Beach

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold Cottage w/ Patio & Grill - Walk to Beach!

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Little Red Cottage - A cozy home steps away from private beach & wine trail.

2.0 star property
10.0 out of 10, Exceptional, (1)
"This sweet cottage is in a charming community, walking distance to a beautiful LI Sound beach. You can walk for miles on this beach connecting with nature. The cottage is in an ideal location for your exploration of the North Fork, with easy access to the South Fork as well. Perfect place for a couple to call home for a month. My elder brother and I used the bedroom and pull-out trundle couch/bed in the living room - both were cozy and comfortable. We loved sitting on the porch listening to the...
The Little Red Cottage - A cozy home steps away from private beach & wine trail.

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries

Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries

7.0 out of 10, Good, (9)
"My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple...
Secluded Lakefront Cottage Near Town Beaches and North Fork Wineries

Craftsman Cottage in Greenport Village

10.0 out of 10, Exceptional, (1)
"Me, my brother and sister in law, their son and his 1 year old daughter. The house suited us well. The house was well appointed and clean. Old craftsman house with nice modern kitchen and bathrooms. Bedrooms were a little tight with Queen beds but not a big deal. NIce big dining table for meals. Private back yard with picnic table. Quiet neighborhood with short walk to downtown."
Craftsman Cottage in Greenport Village

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

9.8 out of 10, Exceptional, (19)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top North Fork Hotel Reviews