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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

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

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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

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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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$280

4 BR / 10 BA / Sleeps 8

Cottage Getaway - Shelter Island 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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$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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$300

3 BR / 2 BA / Sleeps 9

Captain's House in Downtown Greenport Village - Shelter Island 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
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  • 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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$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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$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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$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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$572

3 BR / 2 BA / Sleeps 6

9 Reviews

$572

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Hip & Stylish East Hampton Getaway

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close enough to it all, yet removed enough to feel like you're on a real …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(9)

Stylish nature getaway

Left on Jul 19, 2013 for a stay in July 2013

Loved my stay at Patricia's gorgeous Hamptons home. Loved this place as soon as I walked in. Airy, white and light, with cool furniture and art. Amazing what a dose of trees and a dip in the pool can do for a nature deprived New Yorker! Feels like a total getaway but close enough to East Hampton for anything you need. Woke up every morning to the sound of birds, yoga on the deck, some espresso (…

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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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(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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(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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$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

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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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$345

5 BR / 4 BA / Sleeps 10

1 Reviews

$345

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5 bedrooms East Hamptons house w/ pool, WiFi, BBQ

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Enjoy privacy and peace on a beautiful Northwest Woods parcel with various outdoor entertaining spaces, including large deck with pool. Private 5 bedroom 2700sq foot house. Historic architecture, modern interior design mixed with the landscape's natural beauty provide living at its finest. This home is perfect for …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Great place to stay!

Left on Jun 06, 2013 for a stay in May 2013

This was a great place to spend the weekend. It was comfy, close to the beach and we had plenty of space. Plan on staying again! :)

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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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$925

3 BR / 2 BA / Sleeps 6

1 / 17

$925

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Bridgehampton South, Village Gem!

3 BR / 2 BA / Sleeps 6 | Quick view

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Centrally-located, south of the highway charmer with easy layout and all year round cozy feel. Sun drenched, post modern with vaulted ceilings, oversize windows and exposed beams running throughout house. Expansive great room is fantastic for holiday entertaining. 3 bedrooms, 2 full bathrooms plus spacious outdoor …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$295

2 BR / 1 BA / Sleeps 6

3 Reviews

$295

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Main Street Historic Gingerbread House Full floor

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apartment with five rooms, generously proportioned …
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(3)

Has it all

Left on Nov 14, 2013 for a stay in November 2013

Let me start by saying I have stayed at the Gingerbread House several times over the summer and fall and it is pure joy. this is a quaint historic house totally renovated with tons of character.
Prime Location: Just park your car and you don't have to worry about a thing. It's all literally a short walking distance to a plethora of great shopping, restaurants, boating and beaches and of course, …

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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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$386

3 BR / 3 BA / Sleeps 6

1 / 14

$386

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Secluded, Contemporary House in 4 acres

3 BR / 3 BA / Sleeps 6 | Quick view

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Beautiful, 2300 sq ft single storey, modern, three bedrooms (3 bathrooms) house in Northwest Woods is set in 4 acres of woodland with large heated pool (44' x 16'). Features include 20 foot vaulted ceilings with oversize windows and skylight, 3 spacious bedrooms with 2 en suite bathrooms and a third bathroom; large…
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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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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$195

3 BR / 2 BA / Sleeps 6

1 / 17

$195

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East Hampton retreat with pool and walk th

3 BR / 2 BA / Sleeps 6 | Quick view

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When we vacation we want spotless remodeled accommodations near everything interesting. How about you? Our home is quiet, relaxing, and close to all. Best yet, you'll have your very own 20'x40' salt water pool to enjoy, and you're a 5 minute walk to a private beach. This is a pristine home with all new furnishings…
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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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

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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$1,350

4 BR / 4 BA / Sleeps 8

4 Reviews

$1,350

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Stunning and Spacious. Walk to Harbor and Sunsets!

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

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Reviews

(4)

This striking custom-built Cape Cod design offers space and luxury in a pristine, immaculate vacation home. Virtually new, it features 4 expansive, luxurious bedrooms, 3 1/2 beautifully tiled baths, a designer kitchen with Corian counter tops, state-of-the-art appliances, Mexican tile, and wide oak flooring throughout…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for the elderly

Details

Reviews

(4)

a great surprise

Left on May 16, 2010 for a stay in June 2009

My sister has lived in east hampton for over 25 years so my family has been there quite alot. We have never stayed anywhere except her home. My niece was getting married and the whole family including grandchildren had to find a place to stay. I prefer an upscale hotel but that would not work in this case. The Hamptons Vacations was recommended to us. I was very reluctant. My sister went to check…

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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

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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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$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

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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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$500

6 BR / 4 BA / Sleeps 14

1 / 12

$500

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Beautiful 6BR/4BA East Hampton Home

6 BR / 4 BA / Sleeps 14 | Quick view

Details

6 bedroom, 4 bathroom Contemporary. Open floor plan, soaring ceilings; brand new kitchen and dining area. Pool, outdoor shower, hot tub. 5 minutes to beach, village, 7 minutes to Sag Harbor Village. Also available for holidays and special occasions short term.
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

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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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$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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$257

3 BR / 2 BA / Sleeps 6

1 / 13

$257

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Hamptons Summer Cottage

3 BR / 2 BA / Sleeps 6 | Quick view

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This cottage is located on one of the nicest blocks in Springs area of East Hampton. The house is a cozy ranch, with a Cathedral ceiling in the living/dining area. Relax on our lovely deck surrounded by lawn, trees and gardens and just watch the birds as you sip a drink. This rental has all the the amenities -- …
  • 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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$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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$500

4 BR / 3 BA / Sleeps 10

1 / 33

$500

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Beautiful East Hampton Escape, Heated Pool

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Spacious East Hampton vacation home features four large, furnished bedrooms with oversized master and walk-in closet, three full bathrooms with modern hotel finishes, large custom kitchen with stainless steel and paneled appliances, sunny family/living room with working fireplace, wireless high-speed internet access, …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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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

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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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$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

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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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$357

3 BR / 3 BA / Sleeps 6

1 / 23

$357

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Mini Resort in East Hampton on a private acre

3 BR / 3 BA / Sleeps 6 | Quick view

Details

This immaculate Ralph Lauren furnished home has it all including a Hot Springs Spa, custom Heated Pool with stand alone Pool House, 3000 sq. ft. of decking that wraps around entire back of home leading down to the pool area with all the outdoor furniture/seating you could imagine. Fireplace lights up the cathedral …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$572

4 BR / 2 BA / Sleeps 8

1 Reviews

$572

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Private waterfront setting, kayaks, walk to beach

4 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Come and relax at this peaceful and private home on an inlet of Three Mile Harbor, East Hampton, NY. Great for families and nature lovers.Watch the gorgeous sunsets from benches by the waterside firepit or from the deck while sipping cocktails. Dock (could accommodate up to 24' boat) and kayaks for your use to explore…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

An amazing way to end the summer

Left on Sep 20, 2014 for a stay in August 2014

We rented this property for 10 days the last week of August through Labor Day weekend. It was so much more then we expected. The pictures don't do this place enough justice. The property is surrounded by water and has its own dock with kayaks, which we used every day.

There is a beautiful local beach within easy walking distance, which was fantastic, never crowded and made you feel like you are …

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$500

3 BR / 3 BA / Sleeps 5

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$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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$425

2 BR / 2 BA / Sleeps 5

1 / 7

$425

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Love it Year Round

2 BR / 2 BA / Sleeps 5 | Quick view

Details

Cozy and comfy this house is the perfect place to enjoy the Hamptons in the fall. While it may not be warm enough to swim in the ocean it's the perfect time to take a walk on the beach, enjoy wine tastings, lectures at Guild Hall, the Parrish Museum, shopping, a movie, Starbucks and so much more. East Hampton Book …
    • Suitable for children - ask
    • Suitable for the elderly

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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

    Details

    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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    $500

    3 BR / 2 BA / Sleeps 5

    1 Reviews

    $500

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    Historical Orient Pt. Beach Cottage

    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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    $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

    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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    $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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    $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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    $1,000

    6 BR / 4 BA / Sleeps 12

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    $1,000

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    Hampton's Paradise sag Harbor, Southampton

    6 BR / 4 BA / Sleeps 12 | Quick view

    Details

    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, …
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $300

    2 BR / 1 BA / Sleeps 4

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    $300

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    The Hampton Sack

    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Cute, cozy, well maintained, newly renovated fishermen's cottage located in Maidstone beach area of East Hampton. Open area with kitchen, dining area. 2 bedrooms and 1 bath. Property comes with a small studio in the back of the house that can sleep one additional person. Partial wraparound deck and patio in back. …
    • Internet Access
    • Housekeeping Optional
    • Outdoor Dining Area
    • A/C or climate control
    • Porch
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

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    $1,143

    5 BR / 4 BA / Sleeps 10

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    $1,143

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    Designed as a Luxury Boutique Hotel

    5 BR / 4 BA / Sleeps 10 | Quick view

    Details

    Designer's own home boasts every detail. This stylish home has stainless steel chef's kitchen with wine room, breakfast bar and butler's pantry. Dining room with venetian palster walls and modern crystal chandelier. Living room w fireplace and 50" tv. All marble and travertine baths. Master is en suite. Each bedroom …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $299

    3 BR / 2 BA / Sleeps 4

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    $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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    $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 …
    • Pet friendly
    • Smoking allowed - ask
    • 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
    • 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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    $750

    3 BR / 3 BA / Sleeps 8

    1 / 11

    $750

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    3 Bed 3 Bath East Hampton Summer Rental w/ Pool

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Newly renovated contemporary home sits on 1 acre up on a hill across the street from rolling fields at the edge of the Village. The open layout of the home affords large living space complete with a great room with wood burning fireplace, an open kitchen and dining area. On the bottom level, 3 bedrooms and 2 baths, …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children

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    $429

    4 BR / 3 BA / Sleeps 8

    1 / 18

    $429

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    Newly remodeled mid century modern

    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Walking distance to harbor. 10 minutes north to bay beaches, 10 south to downtown East Hampton and ocean beaches. Upside down house with master bedroom and bath, 25x15 room with grand piano and kitchen upstairs, deck; 3 bedrooms and 2 baths downstairs. Light and airy!
    • Wireless Internet
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly - ask
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