50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
75 properties
Estates Southampton
68 properties
House rentals Montauk
31 properties
Vacation rentals Sag Harbor
30 properties
House rentals Amagansett
13 properties
Apartments Water Mill
12 properties
Bridgehampton
11 properties
East Quogue
10 properties
Apartments Shelter Island
7 properties

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338 Vacation rentals

20

Vacation home in Southampton

Hamptons / Southampton

6 12 1 night min

  • 6 bedrooms
  • sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1,680 / night

$11,760 / week

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from $1,680 / night

11

Vacation home in East Hampton

Hamptons / East Hampton

8 20 7 nights min

  • 8 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A new construction estate in the exclusive Georgica Pond section of East Hampton brings the fabled tradition of Long Island country houses into the here and now. This gracefully proportioned gambrel home continues the proud lineage of East Hampton estates for the New co …see more

from $5,715 / night

$40,000 / week

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Responds fast!
avg. 17 minutes

from $5,715 / night

17

Cottage rental in Sag Harbor

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6,000 / week

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from $900 / night

18

Vacation cottage in Montauk

Hamptons / Montauk

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child friendly
  • Pet friendly
Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to priv …see more

from $334 / night

$2,334 / week

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from $334 / night

21

Home rental in East Hampton

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Green Rock is located in the Northwest Wood section of East Hampton. The property is so well situated you will probably not want to leave it. The moon rises over the water, the sun sets in the back. Turn on the landscape lighting, open a great bottle of wine and enjoy …see more

from $900 / night

$6,300 / week

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from $900 / night

13

Vacation home in East Hampton

Hamptons / East Hampton

5 12 30 nights min

  • 5 bedrooms
  • sleeps 12
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Furnished 5 bedroom 4 bathroom home on a quiet cul de sac. In-law/nanny suite with private bathroom and living room. Viking/subzero appliances with granite countertops. Spacious deck and Porch on one acre piece of property. Great house for entertaining. Air conditioning …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

20

Vacation home with golf nearby in Wainscott

Hamptons / Wainscott

4 8 21 nights min

  • 4 bedrooms
  • sleeps 8
  • 21 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
We are a family of 4. My kids love that I made a tv/playroom next to my kitchen separated from our own TV in the open kitchen/living room space. This house is located in the Best area in the Hamptons. 5 minutes drive from Sag Harbor Main Street, 7 minutes drive to Eas …see more

from $1,800 / night

$9,000 / week

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Responds fast!
avg. 2 hours 37 minutes

from $1,800 / night

(2) Excellent 

12

Vacation home in East Hampton

Hamptons / East Hampton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
In its ideal setting in the beautiful Northwest woods, this property combines serenity and close proximity to East Hampton village (two miles). This three bedroom, two bath contemporary, which is sited on two-thirds of an acre, features a bright, light interior with vau …see more

from $700 / night

$2,950 - $6,950 / week

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from $700 / night

(5) Excellent 

28

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegan …see more

from $2,429 / night

$17,000 - $20,000 / week

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Responds fast!
avg. 2 hours 51 minutes

from $2,429 / night

41

Vacation home in Montauk

Hamptons / Montauk

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
One large fishing cabin from the 20's has been redesigned and renovated with upcycled materials for contemporary loft style living with a Mediterranean touch. 3 bedrooms, 2 bathrooms (claw foot bathtubs), and a loft style common room with cathedral ceiling. Concrete flo …see more

from $600 / night

$5,000 / week

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from $600 / night

9

Hampton Bays Vacation home rental

Southampton / Hampton Bays

3 4 13 nights min

  • 3 bedrooms
  • sleeps 4
  • 13 nights min
  • Child friendly
  • Air conditioning
  • Private garden
BEAUTIFUL BAYFRONT HOUSE AND SEPARATE GUEST COTTAGE !! Near all, restaurants, movie theaters, town, 7/11,Star Bucks, Dunkin Donuts TRAIN, fishing, ocean beaches, swimming and all water activities. BBQ, eat on the deck watch the boats go by. Private fenced in yard. …see more

from $200 / night

$2,800 / week

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from $200 / night

(5) Excellent 

15

Vacation cottage in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The ow …see more

from $500 / night

$3,500 / week

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from $500 / night

(10) Excellent 

26

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
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 o …see more

from $400 / night

$3,000 / week

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Responds fast!
avg. 1 hour 58 minutes

from $400 / night

(5) Excellent 

22

East Quogue Vacation home rental

Hamptons / East Quogue

8 8 2 nights min

  • 8 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
Beautiful two level 4,100 sq. ft. home in East Quogue is sure to accommodate all your summer get away needs. If you enjoy spending quality time together our home provides a large backyard with an in-ground heated pool, and a new BBQ. Than come hang out inside in our g …see more

from $1,200 / night

$8,400 / week

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from $1,200 / night

13

Vacation home in Bridgehampton

Hamptons / Bridgehampton

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Lovely home on prime BH North Street, with privacy and lots to do around. Gourmet kitchen with good knives and all clad. Garden is organic with lots of herbs and flowers. There are 3 whirlpool baths. One king. Size bed is sleep number. Owners want you to enjoy! …see more

from $1,200 / night

$8,400 / week

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from $1,200 / night

(2) Excellent 

15

Vacation home in East Hampton

Hamptons / East Hampton

3 7 4 nights min

  • 3 bedrooms
  • sleeps 7
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spend time relaxing by the heated pool or enjoying the nearby beautiful ocean and bay beaches of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. An open light filled great room floor plan with double height ceilin …see more

from $750 / night

$4,725 / week

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from $750 / night

14

Montauk Vacation home rental

Hamptons / Montauk

3 9 7 nights min

  • 3 bedrooms
  • sleeps 9
  • 7 nights min
  • Child friendly
  • Private garden
DIAMOND BEACH HOUSE ,IS LOCATED IN THE CULLEN SHORES AREA.ONE BLOCK, TO PRIVATE BEACH . HOME HAS TWO DECKS, NEW APPLIANCES ,CEILING FANS THREW OUT. .AND AC IN BACK ROOM SLEEPS 9 .OUTDOOR SHOWER. PRIVATE BACKYARD .THERE IS THE CROWS NEST LOOKOUT, OF THE SOUND .AMAZING SU …see more

from $550 / night

$3,500 / week

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from $550 / night

23

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Elegantly decorated contemporary on a short, quiet dead-end street. Private setting on 1 acre, with stone patio and large deck overlooking the pool and garden. House is set back from the road and surrounded by trees. Newly renovated house with 3 bedrooms and 2 baths, …see more

from $572 / night

$4,000 / week

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from $572 / night

(14) Excellent 

24

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Minimum two-week stay. 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 …see more

from $358 / night

$2,500 - $3,800 / week

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Responds fast!
avg. 3 hours 34 minutes

from $358 / night

(2) Excellent 

30

Shelter Island Vacation home rental

Hamptons / Shelter Island

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
WINTER SPECIAL: Stay for long weekend or Week for $999, plus utils, taxes. Any week, except holidays. Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on bac …see more

from $295 / night

$1,295 - $4,999 / week

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from $295 / night

(1) Excellent 

26

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

6 12 6 nights min

  • 6 bedrooms
  • sleeps 12
  • 6 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining roo …see more

from $3,000 / night

$19,000 / week

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Responds fast!
avg. 3 hours 39 minutes

from $3,000 / night

(2) Excellent 

7

Vacation home in East Hampton

Hamptons / East Hampton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated d …see more

from $370 / night

$2,600 - $5,900 / week

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from $370 / night

(8) Very Good 

11

Vacation b&b in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Car not necessary
This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. One bedroom has a water view, the second bedroom is larger at the front of the house, and they share a dressing room/office. …see more

from $500 / night

$3,500 / week

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from $500 / night

32

Vacation home in Sag Harbor

Hamptons / Sag Harbor

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The calm, honest architecture exudes the modern minimalist atmosphere of this elegant 7-bedroom, 6.5-bathroom vacation rental home in Sag Harbor. Up to 14 travelers will have the opportunity to experience a luxurious Hampton lifestyle with featured amenities including a …see more

from $1,500 / night

$10,500 / week

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Responds fast!
avg. 23 minutes

from $1,500 / night

23

Vacation home in Amagansett

Hamptons / Amagansett

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cath …see more

from $1,200 / night

$8,000 / week

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from $1,200 / night

(1) Excellent 

19

East Hampton Vacation home rental

Hamptons / East Hampton

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
located only 5 minutes from shops and eateries and 5 minutes to the beach. With a serene setting surrounded by mature trees, this home is a haven for ultimate relaxation and leisure. Enjoy poolside luxury by 20X40 pool in very private yard. Low Allergen Environmentchil …see more

from $500 / night

$3,500 / week

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from $500 / night

28

Vacation home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling tog …see more

from $849 / night

$5,943 / week

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Responds fast!
avg. 23 minutes

from $849 / night

(1) Very Good 

10

Vacation home in Water Mill

Hamptons / Water Mill

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Modern 3+ Bedrm/2.5 Bathrm with 70' WATERFRONT in luxurious Water Mill. Leave your car home! 2 Minute stroll to Village for bagels in the morning and Suki Zuki sushi (restaurant) in the evening. Bike/Walk to Ocean/Beach (1.5 Mile). 5 minute walk to Luxury Hampton Jitney …see more

from $680 / night

$5,000 / week

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from $680 / night

17

Hampton Bays Vacation home rental

Southampton / Hampton Bays

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Sunny & Peaceful home within walking distance to the bay and a 15 min bicycle ride to the ocean. With an outdoor fireplace, outdoor shower and spacious backyard the day doesn't have to end. Master bedroom has a queen bed, daybed, and en-suite bathroom. The second bedr …see more

from $650 / night

$3,500 / week

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from $650 / night

(1) Excellent 

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the cente …see more

from $600 / night

$3,000 / week

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from $600 / night

27

Hampton Bays Vacation home rental

Southampton / Hampton Bays

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbe …see more

from $655 / night

$4,585 / week

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from $655 / night

17

Vacation cottage with shared pool in East Hampton

Hamptons / East Hampton

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Charming, private, 2 story cottage with outdoor balconies. "Treehouse" feel with great wooded views. Queen bed, one loft bed, full bath, hardwood floors on second floor. Sitting area, twin bed on first floor with washer/ dryer. Covered balcony with gas fire ring, warm …see more

from $150 / night

$1,050 / week

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from $150 / night

29

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning
The New York coast awaits at this Sag Harbor 4-bedroom, 3-bathroom vacation rental house with additional sleeping arrangements with 2 sofa beds in the den - the perfect destination for up to 10 guests! This home boasts one of the best locations with walking access to pr …see more

from $775 / night

$5,425 / week

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Responds fast!
avg. 23 minutes

from $775 / night

18

East Hampton Vacation home rental

Hamptons / East Hampton

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Ask about children
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! …see more

from $500 / night

$2,000 - $3,500 / week

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from $500 / night

13

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A beautiful custom built 2 bedroom home offers authentic charm and elegance from the finishing to the furnishings. It is located in a waterfront community just steps to the Peconic Bay with access to launching your boat! Enjoy the view of the heated pool from a spacious …see more

from $643 / night

$4,500 / week

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Responds fast!
avg. 1 hour 54 minutes

from $643 / night

8

Vacation hotel apartment in Westhampton

Hamptons / Westhampton

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
Our SeaBreeze Suite sleeps up to 4 guests in two rooms - one queen bed in private bedroom and two twin sized beds in living room - as well as a small kitchen w/ refrigerator, microwave, stove top oven and coffee maker. This suite also has free wifi, premium cable and p …see more

from $150 / night

$700 - $1,000 / week

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Responds fast!
avg. 2 hours 41 minutes

from $150 / night

12

Vacation home rental

Hamptons / Bridgehampton

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
Beautiful contemporary home set on 1.6 private idyllic acres. Perfect for families with children as well as entertaining. Beautiful Bluestone deck and patio. Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Cla …see more

from $1,085 / night

$4,000 - $8,000 / week

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from $1,085 / night

18

East Hampton Vacation home rental

Hamptons / East Hampton

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This stunning contemporary house is set on two private acres in the near Northwest Woods. Bright, white filled with sunlight, this four bedroom, two and a half bath multi-level home has soaring cathedral ceilings on the main level, large king master bedroom suite with …see more

from $500 / night

$2,000 - $6,280 / week

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from $500 / night

20

Vacation home in East Hampton

Hamptons / East Hampton

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Brand New Chic Saltwater Dark Bottom Pool with Tanning Ledge! Whisper quiet retreat for all seasons in updated contemporary saltbox in East Hampton's NW Woods. Close to beach and charming EH and Sag Harbor! Rental contract required. RR # 161918 Also has wood burn …see more

from $390 / night

$5,900 / week

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from $390 / night

5

Vacation home in Bridgehampton

Hamptons / Bridgehampton

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child friendly
  • Ask about pets
Beautiful sundenched hamptons property recently renovated quiet and private yet centrally located to all ocean and bay beaches, shopping and transportation. Bike to beaches, towns of Bridgehampton and Sag Harbor. Vineyards and farm stands just up the street. Dead end s …see more

from $1,950 / night

$13,500 / week

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from $1,950 / night