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Holiday Homes and Apartments Southampton, NY

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$182
Per Night
1 / 34
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Studio, 1 Bathroom, Sleeps 4
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$367
Per Night
1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
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$1,485
Per Night
1 / 55
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7 Bedrooms, 5 Bathrooms, Sleeps 18
Details Reviews (6) Make Enquiry
From
$611
Per Night
1 / 43
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4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
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4 of 5 stars Reviewed 5 August 2012
We stayed with three other couples after a week in NYC and this was the ideal break for us. The house is perfectly located just a 5/10 minute drive from Southampton centre. At...
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From
$611
Per Night
1 / 25
6 Bedrooms, 3 Bathrooms, Sleeps 12
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed 22 September 2014
Everything about renting this property was easy and everything was as expected. The house is beautiful, clean and very well maintained. The layout is great and all the rooms are...
5 of 5 stars Reviewed 3 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...
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From
$611
Per Night
1 / 44
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4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (7) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
Make Enquiry
5 of 5 stars Reviewed 11 June 2014
Pavel was a wonderful host and gave us all the right tips to enjoy the area. The lake(one minute away walk) is wonderful(to swim /kayak or just hang out) and the house is also...
5 of 5 stars Reviewed 10 June 2014
We booked this quite last minute but it was all that we hoped for. Owner gave us some great tips on things to do in the area as well -
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From
$733
Per Night
1 / 13
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3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden
  • Grill
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Relax and unwind in this stunning, newly renovated 3 bedroom, 2 1/2 bath home located in Whalebone Landing, a private waterfront community with a beach on Peconic Bay. The expansive deck leads to the 20x40 heated pool, newly planted gardens, bluestone patio with fire pit and outdoor shower in a... View all property information
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From
$1,528
Per Night
1 / 52
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6 Bedrooms, 7 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This luxurious Southampton estate is set on a large private plot of land. With close proximity to Southampton village and world famous Coopers beach, the location of this estate takes advantage of all that Southampton has to offer. The house has 6 bedrooms 7 bathrooms. A professional gourmet... View all property information
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From
$2,139
Per Night
1 / 11
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Fabulous Bay Front Villa on a private acre in Southampton close to village & Beaches. Beautiful fountain to greet you and your guests to the water front retreat with high end finishes. Vaulted ceilings, Professionally decorated and 6 Bedrooms with 4 1/2 baths with Jetted Tubs & Steam Shower. All... View all property information
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From
$611
Per Night
1 / 17
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
A very private and charming getaway minutes from the the ocean, the bay, and Southampton Village shopping and activities. Also centrally located to the other Hamptons villages and a ferry ride away to Shelter Island and the North Fork, our home is the perfect base from which to explore the beauty... View all property information
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From
$4,889
Per Week
1 / 9
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4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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... View all property information
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From
$1,222
Per Night
1 / 24
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4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Four bedroom.three bathroom house with heated pool on a wooded acre in Southampton. Granite kitchen, deck with grill, peaceful gardens and woodland views, very close to the village, ocean and bay. Previously rented by national magazine. View all property information
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From
$1,467
Per Night
1 / 25
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6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$403
Per Night
1 / 12
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4 Bedrooms, 4 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Charming century-old wood-frame and shingled cottage located in a former artists' colony in Southampton, NY, close to beaches, shopping and sight-seeing. Has been well-maintained and steadily upgraded to respond to modern expectations. Tenants may bring a dog. I am looking for seasonal or monthly... View all property information
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From
$978
Per Night
1 / 22
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Stunning four bedroom home on one plus park-like acre 5 minutes from Southampton and ocean beaches, This home has never been rented before. It boasts an oversized heated gunite pool, spa and cooks kitchen. Make your self at home outside by the pool or on one of the upper decks. Amenities... View all property information
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From
$428
Per Night
1 / 32
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 3 bedroom house located on top of the hill overlooking Peconic Bay. Full Winter Views and partial Summer Views. Downstairs has master bedroom and kitchen and Free Form Dining table with wrap around porch and outdoor seating. Upstairs has deck, large family room with pull out sofa, Large... View all property information
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From
$733
Per Night
1 / 2
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Farmhouse style house in the Village of Southampton within walking distance to train station, railway station, downtown, and bicycle to the beach. House has 2 1/2 bedrooms, 2 1/2 baths, heated swimming pool. NO GROUP Rentals single family only!!!!!!!!!! House only available for a monthly rental... View all property information
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From
$1,161
Per Night
1 / 22
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4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$794
Per Night
1 / 10
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Comfortable 4 bedroom Southampton Home located in a quiet neighborhood just minutes from Peconic Bay. Enjoy a quite afternoon on the hammock, an evening with friends bbqing on the large deck, or a majestic sunset at the the beach by the bay. The Space $125 p/night for each extra person over 5... View all property information
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From
$733
Per Night
1 / 16
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
"South of the Highway," this spacious, open plan home with pool has space for family plus nanny. Garden setting. You'll feel at home, "be" at home. The House - Surrounded by windows, this open-plan home makes you feel like you're living in a garden. With 3-decks and lots of private spots by pool,... View all property information
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From
$1,528
Per Night
1 / 23
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7 Bedrooms, 7 Bathrooms, Sleeps 14
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This estate has 7 bedrooms and 6.5 bathrooms, all bathrooms are marble with high-end fixtures. All bedrooms have 32 inch HDTV's. Boasting 2 living rooms - 1 on the main floor and 1 on the first floor. Beautiful kitchen with wood floors throughout. 3000 square feet of exterior wood deck, which leads... View all property information
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From
$611
Per Night
1 / 8
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Water views through full glass wall of the master bedroom and deck of this smartly restored 1929 cottage on unique road that people walk, jog, & bicycle to its end: an exquisite, near-private, sugarsand beach. Enjoy watching ducks & swans through the picture window of the updated, eat-in... View all property information
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From
$183
Per Night
1 / 3
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
SUCH A BEAUTIFUL LOCATION ! Come stay at our Beautiful Southampton guest house suite. Getaway and visit Southampton towns and shops Great restaurants. Centrally located near vineyards,minutes drive to Southampton town and Coopers beach, the bay beach is 2 minutes away, you can walk it about 1 mile.... View all property information
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From
$2,200
Per Night
1 / 7
6 Bedrooms, 7 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
waterfront villa estate with;everything!!!!! Beds: 3 King Beds, 2 Queen Beds, 1 Double Bed, 2 Sofa Beds, 1 Crib View all property information
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From
$489
Per Night
1 / 24
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
'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... View all property information
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From
$1,222
Per Night
1 / 17
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5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
GORGEOUS Home IN Southampton.. Contemporary home in mint condition condition, simply superb. 15 minutes drive to the Village, bars, restaurants, boutiques and night life, COOPERS BEACH is just few minutes away. You can enjoy the little Peconic just a short walk from the house!!! This two floor... View all property information
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