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$280

4 BR / 10 BA / Sleeps 8

Cottage Getaway - Cutchogue vacation rentals
1 / 19

$280

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Cottage Getaway

4 BR / 10 BA / Sleeps 8 | Quick view

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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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$525

4 BR / 3 BA / Sleeps 8

1 Reviews

$525

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Peconic Perfection: Spacious, Comfortable, NF Cent

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

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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

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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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$150

2 BR / 1 BA / Sleeps 6

1 Reviews

$150

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Cutchogue Beach Cottage

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

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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

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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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$495

5 BR / 3 BA / Sleeps 14

North Fork Loft - Perfect for Wine & Food Weekends - Cutchogue vacation rentals
1 / 13

$495

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North Fork Loft - Perfect for Wine & Food Weekends

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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$300

3 BR / 2 BA / Sleeps 9

Captain's House in Downtown Greenport Village - Cutchogue vacation rentals
1 / 29

$300

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Captain's House in Downtown Greenport Village

3 BR / 2 BA / Sleeps 9 | Quick view

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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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$249

2 BR / 2 BA / Sleeps 6

2 Reviews

$249

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Waterfront Condo C204 @ The Cliffside Resort

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

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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

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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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$300

3 BR / 2 BA / Sleeps 7

1 / 15

$300

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Greenport's 'Old Schoolhouse'

3 BR / 2 BA / Sleeps 7 | Quick view

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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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$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

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

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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

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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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$489

2 BR / 2 BA / Sleeps 6

30 Reviews

$489

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Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!

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

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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

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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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$499

3 BR / 3 BA / Sleeps 8

1 / 8

$499

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Private Waterfront W Beach, New Renovation

3 BR / 3 BA / Sleeps 8 | Quick view

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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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$1,200

6 BR / 5 BA / Sleeps 12

1 / 25

$1,200

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Newly Renovated Southampton Summer Home

6 BR / 5 BA / Sleeps 12 | Quick view

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Recently renovated, beautiful vacation home within a mile of Southampton Village restaurants and shops. It is located on a very quiet and private lane near two beautiful horse farms. This home features six large bedrooms and four and one half baths. The floor plan is open, bright and airy, with a beautiful state …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$2,143

6 BR / 5 BA / Sleeps 12

1 / 13

$2,143

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PRIVATE HISTORICAL HOME AND GUEST HOUSE

6 BR / 5 BA / Sleeps 12 | Quick view

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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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$295

3 BR / 1 BA / Sleeps 6

11 Reviews

$295

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Waterfront North Fork Sunny Home

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

Details

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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$450

3 BR / 1 BA / Sleeps 6

1 / 11

$450

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North Fork Beach House on LI Sound

3 BR / 1 BA / Sleeps 6 | Quick view

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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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$500

6 BR / 3 BA / Sleeps 12

4 Reviews

$500

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6BR Amazing Southampton Home, Private, Pool, Jacuzzi, Village Near All

6 BR / 3 BA / Sleeps 12 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

SUCH A BEAUTIFUL LOCATION ! Come stay at our Beautiful Southampton Home. Visit Southampton town village and shops Great restaurants only 3 min away. Centrally located!THE BEACH IS 1 mile away & Coopers beach is 6 min away . Available for weekly stays in season and 2 night min off season. The house is nestled in a park…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfect for a group getaway!

Left on Oct 02, 2012 for a stay in October 2012

We stayed here for my sister's bachelorette for a weekend getaway in October. 13 girls were able to stay very comfortably. The space was perfect for us (comfortable. spacious and elegant living room, functional kitchen, great hot tub and pool) and well located in Southampton.

Linda, the owner, was extremely accommodating and informative, and went above and beyond to make us feel …

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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

2 BR / 1 BA / Sleeps 4 | Quick view

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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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$2,250

5 BR / 8 BA / Sleeps 10

4 Reviews

$2,250

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Elegant Designer Hamptons Retreat in Sag Harbor

5 BR / 8 BA / Sleeps 10 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

This property is only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is one month during High Season unless you see an availability between rentals. During the off season 2 week rentals may be possible. This elegant 6000 square foot home …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

Fantastic accommodation and lovely destination

Left on Jun 13, 2013 for a stay in May 2013

I would like to say the stay at Lisa Rose's place in Sag Harbour was amazing. The experience started when we first made contact with Lisa Rose through Flipkey - confirmation came through immediately, Lisa always replied to any question we had - then we arrived Lisa was there to meet us and took us through her wonderful home before giving us the keys the house was ours! Located in a gated …

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$533

3 BR / 2 BA / Sleeps 7

1 Reviews

$533

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3 Bdrm Southampton Village House With Heated Pool.

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

LOCATED IN THE VILLAGE PROPER- VERY WALKABLE LOCATION- ******LUXURY AT A BUDGET*****1.5 MILE TO COOPERS BEACH. A NICE SIZE COTTAGE YOU WILL NOT FEEL CRAMPED. It has a lovely flow for entertainment with multiple seating areas. Living area, fireplace area, dining area. Eat in kitchen and a large backyard with large …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

home away from home

Left on Jun 29, 2014 for a stay in September 2013

The house is in a beautiful area that is convenient to everything.

I felt safe and comfortable, had a very relaxing experience staying there- and the home owner couldn't be nicer!!!

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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

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

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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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$950

4 BR / 4 BA / Sleeps 8

1 / 22

$950

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Southampton Sanctuary in European Designer House

4 BR / 4 BA / Sleeps 8 | Quick view

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Contemporary designer home for the well seasoned traveler. Enjoy a gourmet kitchen while your guests relax by the fireplace in the open dining area, in the large comfy entertainment room, or on the wood deck custom dining area for more than 10 people. Designer renovated split-level home offers 4 bedroom and 4 full …
  • Suitable for children
  • Suitable for the elderly - ask

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$400

4 BR / 3 BA / Sleeps 8

3 Reviews

$400

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Hampton Bays, south of 27A

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room on first floor. Deck accessible by wheelchair. …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

Great family vacation w friends!!

Left on Jul 27, 2014 for a stay in July 2014

Just wanted to say what a great house this was- we had 6 young kids with 8 adults and fit great in this house. Huge back yard with plenty of space to play games and have water ballon fights. New weber grill, amazing deck with beautiful furniture. This house had everything! 3 full baths to accommodate everyone and a really close car ride to the beach and town. Would totally recommend this …

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$125

0 BR / 1 BA / Sleeps 4

1 Reviews

$125

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Cute Hamptons Cottage

0 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

***THIS PROPERTY IS AVAILABLE FOR A WINTER RENTAL STARTING OCT. 1 2014 TO APRIL 30 2015 PLEASE INQUIRE. Cute well decorated cottage in the North Sea area of Southampton. North Sea is a historic area of Southampton, NY. The cottage is located just behind one of Long Island's largest bodies of fresh water, Big …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great place!

Left on Jul 16, 2014 for a stay in July 2014

Wonderful cottage in a great location. Short trip to town, the beach and restaurants all around. I can't wait to come back. Property was very easy to book and the overall condition of the property was great.

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$275

2 BR / 2 BA / Sleeps 6

1 / 8

$275

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New Renovation, Wine Country Cottage, Water Views

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
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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

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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$800

4 BR / 4 BA / Sleeps 10

1 / 15

$800

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Post Modern Quaint Home Near Beach

4 BR / 4 BA / Sleeps 10 | Quick view

Details

Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min drive to bay beach, fifteen min to ocean beach and twenty min …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

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$900

4 BR / 3 BA / Sleeps 6

1 / 17

$900

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SAG HARBOR MODERN HOME WITH AMAZING SUNSET VIEWS OVER BAY

4 BR / 3 BA / Sleeps 6 | Quick view

Details

Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer vacation. A short ride to Main Street, Sag Harbor, short walk to bay beach.
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children

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$2,857

7 BR / 7 BA / Sleeps 10

1 / 20

$2,857

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Beautiful Estate home in the Hamptons, New York

7 BR / 7 BA / Sleeps 10 | Quick view

Details

This beautiful estate home in Water Mill, New York borders the prestigious Matt Lauer's 40 acre horse farm with distant ocean views. This estate features 7 bedrooms with 7 en suite bathrooms, 2 1/2 baths, two master bedrooms. There are five full masonry fireplaces, pool room, wine room, cigar room, 15 seated high …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$666

5 BR / 10 BA / Sleeps 16

1 / 7

$666

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SOUTHAMPTON VACATION HOME

5 BR / 10 BA / Sleeps 16 | Quick view

Details

You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly or seasonal. In the off-season, September 2014 …
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Pet friendly - ask
  • Suitable for children - over five
  • Suitable for the elderly - ask

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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

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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$145

3 BR / 2 BA / Sleeps 4

2 Reviews

$145

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Bay House C1860 two family

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

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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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$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

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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$500

3 BR / 3 BA / Sleeps 5

1 / 35

$500

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Shelter Island, Contemporary and Private

3 BR / 3 BA / Sleeps 5 | Quick view

Details

Contemporary, light filled 3 bedroom, 3 bath home located near South Ferry with easy access to the Hamptons. The lovely open floor plan features an array of contemporary art and sculptures, a living room with vaulted ceiling and fireplace, state-of-the art kitchen and dining room, all having access to a spacious deck …
  • 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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$572

4 BR / 2 BA / Sleeps 8

1 / 9

$572

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SOUTHAMPTON, LUXURY 4 BED 2 BATH WITH NEW POOL!!!!

4 BR / 2 BA / Sleeps 8 | Quick view

Details

Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre preserve, …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$250

3 BR / 2 BA / Sleeps 7

1 / 12

$250

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Luxury Beach House for the Price of a Hotel Room

3 BR / 2 BA / Sleeps 7 | Quick view

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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

4 BR / 4 BA / Sleeps 8

2 Reviews

$500

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Historic Vineyard Farmhouse with private beach

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

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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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$350

4 BR / 4 BA / Sleeps 10

1 / 16

$350

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Eclectic Round House-4Bedroom+Cottage+Pool-1.5Acr

4 BR / 4 BA / Sleeps 10 | Quick view

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This eclectic 'Round' house is a one of a kind on Shelter Island. Sited on 1.5 acres in Hay Beach with slices of bay views, this upside down house offers 4 Bedrooms and 2 Baths on the ground floor with an open layout upstairs which includes the living and dining room, kitchen, ½ bath, and covered in porch. The …
  • 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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$1,200

5 BR / 4 BA / Sleeps 9

3 Reviews

$1,200

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Burns Cottage

5 BR / 4 BA / Sleeps 9 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

A time and place you will remember fondly forever. Owned and run by the proprietors of the Trip Advisor #1 rated accomodation on Shelter Island - The House on Chase Creek- this home is not a cottage at all, really, but when built by the Burns Family in 1900 that was what all the vacation homes were callled no matter …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Perfect vacation retreat

Left on May 27, 2010 for a stay in May 2010

Dear Bill and Sharon,

Burns cottage was wonderful. Every room was warm and inviting. The house had plenty of room for our extended family, the kitchen was well equipped. We enjoyed having lots of space both indoors and outdoors which allowed us to gather as a group or to find quiet time to ourselves. The wrap around porch overlooking the water was such a nice place to gather for morning coffee. …

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$3,500

7 BR / 7 BA / Sleeps 16

1 / 12

$3,500

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The Residences of Bridgehampton - South -7 BR, 7BA

7 BR / 7 BA / Sleeps 16 | Quick view

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The property is located in the hills of Bridgehampton nestled on six wooded acres between the village of Bridgehampton and the town of Sag Harbor. The house is secluded down a private winding driveway about 800 ft from the main road. The house is a 7,200 sq. ft. classically planned farmhouse surrounded by beautiful …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$400

4 BR / 2 BA / Sleeps 10

1 / 24

$400

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4BR Southampton Home Heated Pool & Jacuzzi sleeps 10, 3 min to village & Beach

4 BR / 2 BA / Sleeps 10 | Quick view

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"This home is perfectly located in Southampton. It is a 4 Bedroom and it sleeps 10 people. The house is perfectly located in the heart of the Hamptons and has a large yard that is private and just beautiful. There is a nice HUGE built in Jacuzzi & Heated Pool in the yard for you to enjoy as well as a BBQ on a Large …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$120

2 BR / 1 BA / Sleeps 4

1 / 13

$120

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recently renovated charming, vacation home

2 BR / 1 BA / Sleeps 4 | Quick view

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Ideal get-a-way home; minutes from bay and beach, on 1/3 acre wooded lot. This home away from home is fully equipped with all the desired amanities. Central air condition. Fully equipped kitchen: gas oven and stove, dishwasher, trash compector and microwave oven. Includes; 2 bedrooms, livingroom, separate dining …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$325

2 BR / 2 BA / Sleeps 6

1 / 20

$325

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>>> ROMANTIC Beach Getaway! Seclusion, Waterfalls

2 BR / 2 BA / Sleeps 6 | Quick view

Details

With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your desired dates. …
  • Internet Access
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  • A/C or climate control
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,000

6 BR / 4 BA / Sleeps 12

1 / 7

$1,000

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Hampton's Paradise sag Harbor, Southampton

6 BR / 4 BA / Sleeps 12 | Quick view

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OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather tennis, central air, …
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  • Wheelchair accessible - ask

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$1,500

4 BR / 3 BA / Sleeps 10

1 / 15

$1,500

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Watermill estate on pond

4 BR / 3 BA / Sleeps 10 | Quick view

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Four bedroom 4000sf house on 8.8 acres of gorgeous, park like property, with 3 acre private pond/lake, and free form gunite pool,right in the heart of Watermill/Southampton. !0 blocks off of Montauk Hwy, 4 minutes to ocean, 5 mins to town of Southampton. Fantastic location! Also has central air, huge kitchen,wifi, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$743

9 BR / 4 BA / Sleeps 18

3 Reviews

$743

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Secluded Mini Estate in Hamptons

9 BR / 4 BA / Sleeps 18 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Walk to beach. Enjoy sunsets over the bay in this beautifully designed contemporary central hall Colonial on 1.6 acres. Extremely large 9 bedrooms, 3.5 baths with state-of-the-art kitchen, formal dining room, large living room with fireplace and billiard room , ping pong room and full exercise gym. Olympic size heated…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

A Fabulous Indulgence

Left on Jan 24, 2014 for a stay in August 2013

I literally just wanted some time off to spend with my kids and husband and a few close relatives and friends but didn't want to go so far away. It must have been through the grace of God that I came across this ginormous house and for the price the owner was asking for...practically a steal! I'm so happy in the decision I made in renting this home as opposed to just practically handing away my …

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$1,150

4 BR / 2 BA / Sleeps 10

1 / 19

$1,150

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Hamptons Lofty Beach Barn - Pet Friendly

4 BR / 2 BA / Sleeps 10 | Quick view

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Lofty beach barn! Very unique & tastefully decorated property with brand new furnishings and pool. Authentic Post and Beam Barn House located in the picturesque town of Water Mill in Southampton, NY. Southampton is home to the world famous Coopers Beach, Duck Walk Vineyard and the Parrish Museum. This open & …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$250

1 BR / 1 BA / Sleeps 2

1 / 9

$250

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Romantic Luxury Winery Apartment

1 BR / 1 BA / Sleeps 2 | Quick view

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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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$299

3 BR / 2 BA / Sleeps 4

1 / 7

$299

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Sunset Beach....Shelter Island Farmhouse: Steps to Beach + Golf Course

3 BR / 2 BA / Sleeps 4 | Quick view

Details

Large Shelter Island Farmhouse Close to all - steps from the golf course and beach 46 West Neck Road - overlooks Town Golf Course+ 1 Block to Sunset Beach + Town Boat Launch 3 bedrooms with AC (one queen, 2 twins, bring sheets + towels), 2 baths + outdoor shower, Dining Room, Living Room, Large Kitchen, Large Front …
  • A/C or climate control
  • Deck
  • Freezer
  • Refrigerator
  • Stove or Oven
  • Pet friendly - ask
  • Suitable for children

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$321

4 BR / 4 BA / Sleeps 10

1 / 5

$321

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Southold Waterfront family Home

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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$1,400

6 BR / 7 BA / Sleeps 17

1 / 6

$1,400

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Renovated Farmhouse - top design & walk to beach!

6 BR / 7 BA / Sleeps 17 | Quick view

Details

About Seven Newly renovated in 2014, SEVEN offers a selection guest rooms for various combinations of guests, with king, queen, double queen and double twin rooms. Each guestroom includes air conditioning, a flat screen television, light seasonal goose down comforters, 100% cotton linens, and a contemporary private …
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  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,100

4 BR / 9 BA / Sleeps 12

1 / 20

$1,100

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Paradise

4 BR / 9 BA / Sleeps 12 | Quick view

Details

Southampton House Rental Photos and Description 4 Bedrooms, 3 Bathrooms, Sleeps 10 Newly acquired first time offering, completely renovated designer's home. Minutes to all Southampton's ocean beaches, . Backing onto a preserve, it is 3 miles to the ocean beaches and a mile from the village of Southampton. This 2400 …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Parking
  • Grill
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