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$249

4 BR / 3 BA / Sleeps 8

2 Reviews

$249

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North Fork House with Private Beach Access

East Marion house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, including master bedroom with en suite bath, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children

Details

Reviews

(2)

We had a perfect weekend with son and grandchildren at this beautiful house

Left on Sep 10, 2014 for a stay in September 2014

The house is warm, cheerful, spacious and bright. It was wonderful to have breakfast, moon-lit dinners on the deck. Indeed the bunnies and deers visited us in the garden as Jane described.

The beach is truly private and beautiful. The grandchildren enjoyed the kayaks, the toys and loved the swings, play area in the garden. My son had a great snooze in the hammock.

The kitchen is very well …

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$295

3 BR / 1 BA / Sleeps 6

11 Reviews

$295

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Waterfront North Fork Sunny Home

Southold house
3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 11 Reviews

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Reviews

(11)

Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and custom light fixtures. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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Reviews

(11)

the property is charming and the hosts delightful and helpful

Left on Jun 12, 2013 for a stay in June 2012

The propsety offers seclusion from the hustle and bustle, but all the delights of the North Fork are right there for the enjoying. The farm stands, wineries and eateries and lovely beaches and boating and golf... friendly towns and relaxed people! The sunsets and night sky are a gorgeous back drop to a comforable, well equipped cottage whose owners are commited to esnuring you enjoy your stay.…

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$314

2 BR / 2 BA / Sleeps 8

Beach Side Modern Home With Heated Pool - North Fork vacation rentals
1 / 10

$314

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Beach Side Modern Home With Heated Pool

Orient house
2 BR / 2 BA / Sleeps 8 | Quick view

Details

All newly renovated and exquisitely appointed home sits on a half acre in the private community of Green Acres steps away from the beaches in unspoiled Orient Point. Designer Rena Wilhelm decorated the home in a crisp ‘beachy’ décor. House amenities include central air conditioning, cable TV with premium channels…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$350

4 BR / 3 BA / Sleeps 8

1 Reviews

$350

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Peconic Perfection: Spacious, Comfortable, NF Cent

Peconic house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

A 4 bedroom home, located in Peconic, steps from a private, white sand Bay beach. Relax with long walks on serene beach, fish, bike, tour wineries, enjoy the bounty of land and sea, and unwind in your quiet surroundings. Our house is a large, comfortable, family-equipped 4 bedroom, 3 bath ranch with a screened-in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Spacious, centerally located!

Left on Nov 20, 2014 for a stay in November 2014

Rented the house for the weekend. Miles from wineries and near by towns.

House was very spacious, one hallway of 3 bedrooms. It was nice that the bedrooms were away from the kitchen.

Will definitely go back in spring or early fall to enjoy their backyard and local wineries.

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$249

2 BR / 2 BA / Sleeps 6

2 Reviews

$249

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Waterfront Condo C204 @ The Cliffside Resort

Greenport condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Overview: Waterfront Water's Edge luxury suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes. Details: Offered by Tocaro Realty, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Great location and accommodation

Left on Aug 08, 2014 for a stay in July 2014

Terrific Two bedroom condo on the water. Was there for July 4th, tons to do. Minutes from shelter island and views to die for.

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$280

4 BR / 10 BA / Sleeps 8

Cottage Getaway - North Fork vacation rentals
1 / 20

$280

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Cottage Getaway

Greenport house
4 BR / 10 BA / Sleeps 8 | Quick view

Details

A gem of a getaway! There are four bedrooms, of which three are located upstairs. Two of the upstairs bedrooms share one new en-suite bathroom. One bedroom upstairs has it's own en-suite bathroom. The bedroom on the ground floor has an en-suite water closet and another full bathroom. The cottage also boasts a newly …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Parking
  • Suitable for children

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$489

2 BR / 2 BA / Sleeps 6

30 Reviews

$489

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Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!

Greenport condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 30 Reviews

Details

Reviews

(30)

As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at Greenport, New York, …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(30)

The Perfect Stay

Left on Jun 05, 2010 for a stay in May 2010

We could not have been more pleased with Cliffside. As you can see I have rated everything with FIVE STARS. The management were charming and very helpful. We rented the activity room for a small family party which was a huge success and anyone involved in organising/cleaning/providing extra glasses/ice etc could not have been more helpful. I would, however, make two comments about the furnishings…

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$200

3 BR / 2 BA / Sleeps 6

1 / 8

$200

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Water View Summer Rental Cottage

Southold cottage
3 BR / 2 BA / Sleeps 6 | Quick view

Details

This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country setting,where one …
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Porch
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$186

3 BR / 2 BA / Sleeps 6

8 Reviews

$186

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Adorable, Updated Farmhouse; Walk to Beach & Town!

Southold house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

This charming farmhouse is just what you've been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and has just been …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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Reviews

(8)

Perfect Modern North Fork Vaca!

Left on Aug 29, 2011 for a stay in June 2011

The house is really adorable and cozy, and perfect for a fun group of friends or family. A really short walk to a great beach and cute town. We would definitely recommend it! The owners are really nice too!

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$350

2 BR / 1 BA / Sleeps 7

1 / 4

$350

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Soundfront 1910 Rustic Secluded Cottage

Peconic cottage
2 BR / 1 BA / Sleeps 7 | Quick view

Details

Tranquil / SECLUDED Beachfront Cottage. Spectacular Sunsets / Views Over Long Island Sound. Secluded: Kayaking, Swimming, Snorkeling, Fishing, In Long Island Sound. For children: Nearby Goldsmith Inlet Park offers flotation device "surfing"; nearby petting zoo, Goat Farm; Splish Splash Water Park. 1 Acre Wooded …
  • Waterfront
  • Ocean or water views
  • Fireplace
  • Porch
  • Parking
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$495

5 BR / 3 BA / Sleeps 14

1 / 13

$495

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North Fork Loft - Perfect for Wine & Food Weekends

Mattituck condo
5 BR / 3 BA / Sleeps 14 | Quick view

Details

The Space The New York TImes Real Estate Section on Sunday, Feb. 9th, 2014, talked about the multi-million dollar homes being built in the Hamptons. The article said, "The look of the homes is evolving: modern is making a comeback, but modern in the guise of barnlike. 'The modern barn is the Hampton equivalent of a …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$499

3 BR / 3 BA / Sleeps 8

1 / 8

$499

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Private Waterfront W Beach, New Renovation

Southold house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with unrivaled water and …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$150

2 BR / 1 BA / Sleeps 6

1 Reviews

$150

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Cutchogue Beach Cottage

Cutchogue cottage
2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing. There is one full bath …
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Adorable Beach Cottage Even in Winter

Left on Mar 23, 2015 for a stay in March 2015

So many great things to say about this little gem! The décor was beachy and relaxed, rooms were comfortable, supplies were perfect for our little families needs. The beach is a quick walk up the block and we enjoyed it, the tire swing and little playground even on days when it snowed. The cottage was warm and cozy with lots of games, books, etc. No one even missed having a tv! We would love to …

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$409

2 BR / 2 BA / Sleeps 6

24 Reviews

$409

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New North Fork Beach Condo, Pool, Resort, Heart of the Wineries

Greenport condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 24 Reviews

Details

Reviews

(24)

Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer on-site, beach.
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(24)

In general I would...

Left on Aug 03, 2010 for a stay in July 2010

In general I would rate my stay 5 stars, but for the fact that the Wifi service was did not work as advertised. Beyond that, the amenities are excellent and the property wonderful. I look forward to my return.

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$175

2 BR / 1 BA / Sleeps 4

1 Reviews

$175

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Historic White Blossom House - Circa 1830 Apartmen

Southold condo
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork Wine Country and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Cozy and comfortable stay

Left on Oct 14, 2014 for a stay in October 2014

Mark & Mona's historic apartment was a delight. It was small but cozy and clean. Our only surprise was that we didn't realize the bathroom was located inside one of the bedrooms, making it slightly uncomfortable for one of the couples.

I'd highly recommend their apartment #3 for one couple or a small family.

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$300

3 BR / 2 BA / Sleeps 9

1 / 29

$300

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Captain's House in Downtown Greenport Village

Greenport house
3 BR / 2 BA / Sleeps 9 | Quick view

Details

The Space Located on a tree lined street this sun-filled two story house sleeps 8 people +. It features 3 bedrooms, 2 bathrooms, an eat in-kitchen and spacious living area with TV and wifi. There are 2 queen size beds, 2 full size beds and a queen size sleeper sofa. The private backyard offers plenty of space to …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children

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$1,167

6 BR / 5 BA / Sleeps 12

1 / 13

$1,167

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PRIVATE HISTORICAL HOME AND GUEST HOUSE

East Marion house
6 BR / 5 BA / Sleeps 12 | Quick view

Details

Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master with an attached private office, 2.5 baths, living, dining, entertaining spaces and a generous eat in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$250

2 BR / 1 BA / Sleeps 6

1 / 17

$250

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Soundside Cottage

Southold cottage
2 BR / 1 BA / Sleeps 6 | Quick view

Details

This charming cedar shingled beach cottage is located 45 feet from Long Island Sound with steps leading down to its own private beach. The cottage is surrounded by a wood deck perfect for watching spectacular sunsets...each night, a unique palette of pink, blue and violet sky as the sun drops into the water before …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

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$145

3 BR / 2 BA / Sleeps 4

2 Reviews

$145

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Bay House C1860 two family

Greenport house
3 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Our one bedroom,kitchenette/ dining room & foldout queen size couch in living downstairs sleeps four comfortable . Backyard garden. Just forty yard walk to our block pier. 150 yard walk into town. The heart of Greenport Village on the best block in our Village no need for your once you arrive \walk or bike …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • Patio
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

A jewel in Greenport

Left on Aug 29, 2014 for a stay in August 2014

I hate to let anyone know about this place since my family (husband and two teenagers) had such a wonderful time and want to return next year and worry that if people discover Greenport and Joe's apartment that we will not be able to book it next year. Greenport is a lovely town, close to the vineyards, farmer's markets, Sag Harbor, Orient Point and Shelter Island, and Joe's apartment was …

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$275

2 BR / 2 BA / Sleeps 6

1 / 14

$275

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New Renovation, Wine Country Cottage, Water Views

Cutchogue cottage
2 BR / 2 BA / Sleeps 6 | Quick view

Details

This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house. There are a/c units in …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$429

4 BR / 4 BA / Sleeps 8

1 / 23

$429

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New Pool & Hot Tub area at our Orient Point Home

Orient house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Enjoy gorgeous water views of Gardiner 's Bay from this immaculate Victorian home situated on 1 acre. This spacious and beautifully decorated home comfortably accommodates 8 adults. Beds: 1 King Bed, 2 Queen Beds, 1 Double Bed
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$295

2 BR / 1 BA / Sleeps 4

1 / 11

$295

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Beach House In Wine Country; Huge Sun Room

Southold cottage
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable bedrooms; one with queen …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$150

2 BR / 1 BA / Sleeps 4

1 / 19

$150

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Historic White Blossom House 1830 - Upstairs Apa

Southold condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower ceilings (6-1 to 6-…
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children - ask

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$500

3 BR / 2 BA / Sleeps 5

1 Reviews

$500

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Historical Orient Pt. Beach Cottage

Orient house
3 BR / 2 BA / Sleeps 5 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

Pernchief Cottage Located In The Village Of Orient Is The Perfect Place To Summer With Family And Friends. Front Porch Offers Lovely Views Of The Bay. Wide Pine Floorboards, Great Architectural Detils Abound. Property Is Beautifully Set On 1/2 Acre With Lovely Gardens And A Tranquil Pond. Charming historical cottage …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Not worth it

Left on May 29, 2014 for a stay in May 2014

Great area but home is in poor condition. Decorated very cute and clean but all uneven floors, very cold inside house, no tv (although it was promised), not worth the price. Area is nice and neighbors kind and friendly so it's too bad house felt like we were camping :-(

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$321

4 BR / 4 BA / Sleeps 10

1 / 5

$321

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Southold Waterfront family Home

Southold house
4 BR / 4 BA / Sleeps 10 | Quick view

Details

This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central air-conditioning, …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

3 BR / 2 BA / Sleeps 6

1 / 15

$300

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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home. Beautiful, all wood …
  • Suitable for children
  • Suitable for the elderly

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$175

2 BR / 1 BA / Sleeps 4

1 Reviews

$175

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Historic White Blossom House - Circa 1830 Cottage

Southold cottage
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork Wine Country and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Patio
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Home Away from Home

Left on Jun 03, 2014 for a stay in June 2014

I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway. Mark and Mona are delightful to deal with and very accommodating.. The cottages are quaint and comfy with a living area and patio space outside. There was even a bbq (we did not use but good to know if we rent in …

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$225

2 BR / 1 BA / Sleeps 4

1 / 18

$225

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Historic White Blossom House 1830 - Large Unit O

Southold condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Representing the owner's suite is the Unit One apartment in the Historic White Blossom House. Newly renovated, floors, kitchen and bath completely updated. Kitchen updated with period country deep sink and fixtures. You will be very comfortable in this large apartment with living room, family room, dining area and…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$250

1 BR / 1 BA / Sleeps 2

1 / 9

$250

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Romantic Luxury Winery Apartment

Jamesport condo
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Spend a relaxing few days at our romantic vineyard and winery in our newly finished 650 sq. ft. luxury apartment situated on beautiful Manor Lane in Jamesport. Our one bedroom (queen size bed), bath w/shower, large open living room, kitchenette, cathedral ceiling, flat screen TV, Cable, WiFi, central air/heat is …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Parking

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$225

2 BR / 1 BA / Sleeps 4

1 / 12

$225

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Secluded Lakefront Cottage Near Beaches & Wineries

Southold house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the deck with a sunset …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$250

3 BR / 2 BA / Sleeps 7

1 / 12

$250

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Luxury Beach House for the Price of a Hotel Room

Southold house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and many other attractions…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$500

3 BR / 2 BA / Sleeps 6

1 / 16

$500

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Private renovated farmhouse near sea and vineyards

Southold house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and ceiling fans, sliding …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$190

2 BR / 1 BA / Sleeps 4

1 / 7

$190

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Lakefront House in L.I. Wine Country

Southold house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

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$450

2 BR / 1 BA / Sleeps 5

1 / 5

$450

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Charming country cottages

East Marion cottage
2 BR / 1 BA / Sleeps 5 | Quick view

Details

North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air conditioning and heat, gas …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Patio
  • Parking
  • Suitable for children
  • Suitable for the elderly - ask

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$286

2 BR / 2 BA / Sleeps 6

1 / 19

$286

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Classic North Fork Farmhouse

Jamesport farmhouse / barn
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Spend your vacation time in this classic North Fork Farmhouse located central to fabulous bay beach and the quaint hamlet of Jamesport. Easy access via Hampton Jitney to/from NYC. Quietly nestled on an acre of farmland with fruit trees and vegetable/flower gardens, plus the back drop of distant farm fields and …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Porch
  • Pet friendly - ask
  • Suitable for children

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$500

4 BR / 4 BA / Sleeps 8

2 Reviews

$500

Inquire

Historic Vineyard Farmhouse with private beach

Southold house
4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your stay. The large …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Perfect Location

Left on Sep 09, 2013 for a stay in August 2013

Very nicely situated rental. Close walk to the private beach, serene setting with a view of a vineyard. The house was perfect for 2 families with children. Functional kitchen, outdoor grill and most amenities one would expect. The house is older and some bedroom dressers need to be updated, however the place is spotless with comfortable beds. Close proximity to grocery shopping in Southold as …

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$295

3 BR / 2 BA / Sleeps 6

1 / 10

$295

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2 Bedroom House With Detached Studio, Water Views

Southold cottage
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house with Queen, two twins with pullout beds and the detached studio cottage with queen bed . From September through June only the studio (sleeps 2 + cot for child) is available for rent. In …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$299

2 BR / 2 BA / Sleeps 6

1 / 9

$299

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Luxurious Waterfront Condo at The Cliffside Resort

Greenport condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at Greenport, New York, …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for the elderly - ask

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$215

4 BR / 2 BA / Sleeps 11

3 Reviews

$215

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Family and Friends in Greenport

Greenport house
4 BR / 2 BA / Sleeps 11 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning fireplace has sliding …
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Family Fun in Greenport, indeed!

Left on Sep 10, 2010 for a stay in August 2010

My husband, 3 year old son, my parents, and I enjoyed a great vacation in Greenport, and this house was a big part of it. It is well set up, with a bedroom and sitting room and full bath downstairs and up (so good for 2 couples) and plenty of fold out coaches plus two twin beds and a futon for the kiddoes. Thoughtfully decorated -- very cozy. Very comfortable, well stocked for cooking, and …

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$450

3 BR / 2 BA / Sleeps 8

6 Reviews

$450

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Waterfront Beach House - Long Island North Shore

North Fork house
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Located on the bluff with amazing views of the Long Island Sound around the year - This is our Waterfront Heaven. Set in a quiet neighborhood, the house is located on the bluff, about 85 feet above sea level. The house is facing the sea and the views are breathtaking. Conveniently located only about 1:20 min drive (60…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

Paradise away From Home

Left on Sep 18, 2012 for a stay in April 2012

I loved this house so much. The view, first of all, is simply amazing. It's as if you were on a ship. You see the ocean straight from the windows, from the deck, from the garden... You can hear the gentle sound of the waves when you're outside too. It is an ideal home for winter or summer. Inside, everything is convenient, modern, nice and clean. Ideal with kids, the house is actually child …

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$250

1 BR / 1 BA / Sleeps 4

2 Reviews

$250

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John Andrew's Cottage

Southold cottage
1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

John Andrew's Cottage is a "turnkey" experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a livingroom filled with …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Patio
  • Parking
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

perfect getaway

Left on Aug 26, 2013 for a stay in August 2013

We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and made sure we had everything we needed for our stay. We couldn’t have asked for a better place to take some time and relax before the big day. The excellent North Fork Table & Inn is right across the street, and the…

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$450

3 BR / 1 BA / Sleeps 6

1 / 17

$450

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North Fork Beach House on LI Sound

Peconic cottage
3 BR / 1 BA / Sleeps 6 | Quick view

Details

Enter a world of tranquility and surround yourself with the beauty of nature! Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is remodeled with stainless steel …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$275

4 BR / 2 BA / Sleeps 6

1 / 24

$275

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Mattituck-Wines and Waves

Mattituck house
4 BR / 2 BA / Sleeps 6 | Quick view

Details

Listen to the ocean waves and smell the tomotoes ripening on the vine from your deck at this meticulous beach house in exclusive Captain Kidd Estates. You will feel like you have unearthed buried treasure when you experience the lore of the North Fork and then retreat to this cozy luxury property which accomodates up …
  • Outdoor Dining Area
  • Deck
  • Suitable for children
  • Suitable for the elderly - ask

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$325

2 BR / 2 BA / Sleeps 4

1 / 5

$325

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Sannino Vineyard Bed & Breakfast

Cutchogue B&B
2 BR / 2 BA / Sleeps 4 | Quick view

Details

In the heart of the North Fork in Wine Country, Our Exclusive Suites have all of the amenities: Private Entry, King size bed, Dining area, Wi-Fi, Living Area, A/C, Wine refrigerator, Private Balcony/Deck overlooking the vineyard, 42″ Flat screen HDTV, Custom marble bath with shower, Bathrobes, iPod docking station, …
  • Internet Access
  • A/C or climate control
  • Porch
  • Parking
  • Linens Provided
  • Suitable for the elderly

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$250

3 BR / 2 BA / Sleeps 7

1 / 15

$250

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Greenport's 'Old Schoolhouse'

Greenport house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

The Space The Old Schoolhouse tells a family story, dating back to the 1880's. This charming farmhouse, built by the Burt family in the 1880's, was first used as a schoolhouse, then transformed into a farmhouse. The Burt family updated the house in 2005 with the most energy efficient systems, so the charm is intact…
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

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$275

4 BR / 2 BA / Sleeps 8

1 / 21

$275

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Renovated North Fork Home Close to Beach& Wineries

North Fork cottage
4 BR / 2 BA / Sleeps 8 | Quick view

Details

A renovated home in the heart of the North Fork near the beach and several wineries. Please inquire about weekends, weeks or monthly/summer rental for 2015. Sleeps 8 Enjoy a bright renovated home with 12 skylights, cathedral ceilings and entirely new furnishings only ¼ mile to Cutchogue harbor and ½ mile to New …
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$250

2 BR / 1 BA / Sleeps 4

1 Reviews

$250

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Lake House in Natural Setting Near L.I. Wineries

Southold house
2 BR / 1 BA / Sleeps 4 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • Garden
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Dark, mildewy, musty, depressing

Left on Sep 02, 2012 for a stay in July 2012

The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was the awful smell of mildew. The whole house smelled old and musty, like it hadn't been aired in a very long time. We were told by the owner (who lives in Oakland, CA,) that a neighbor would clean the property before we …

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$343

2 BR / 1 BA / Sleeps 6

2 Reviews

$343

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Charming 2BR in Heart of North Fork, Walk to Beach

Southold house
2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

**New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground, lifeguard and bathrooms (…
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

Very nice house

Left on Sep 21, 2011 for a stay in September 2011

Great house. Very clean and comfort. We wish we can stay longer. House owners are very nice. If we go to long island again we will rent this house again.


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