50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
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Estates Southampton
36 properties
Vacation rentals Sag Harbor
31 properties
House rentals Montauk
24 properties
Apartments Hampton Bays
16 properties
House rentals Amagansett
12 properties
Bridgehampton
12 properties
East Quogue
11 properties
Apartments Water Mill
9 properties

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240 Vacation rentals

20

Vacation home in Southampton

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 $1510 / night

$10570 / week

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Responds fast!
avg. 3 hours 34 minutes

from $1510 / night

18

Vacation cottage in Montauk

Hamptons / Montauk

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $300 / night

$2100 / week

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from $300 / 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 $5715 / night

$40000 / week

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from $5715 / 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

$6000 / week

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Responds fast!
avg. 3 hours 55 minutes

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 $1000 / night

$7000 / week

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from $1000 / night

(5) Excellent 

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
  • Suitable for children age 5+
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. Each bedroom has a water view, and they share a dressing room/office. Enjoy the spacious porch, that includes an eating ar …see more

from $275 / night

$1700 - $2750 / week

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from $275 / night

24

Home rental in Sag Harbor

Hamptons / Sag Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape from reality in this charming 2-bed, 2-bath Sag Harbor house, which sleeps up to 6. Located just minutes from a private beach, restaurants and shopping, this darling abode is the ideal destination for those looking to explore the Hamptons! You’ll know you made t …see more

from $449 / night

$3143 - $6293 / week

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Responds fast!
avg. 28 minutes

from $449 / night

31

Vacation home in East Hampton

Hamptons / East Hampton

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, and 50-foot pool with 10 chaise lounge chairs, you’ll feel a …see more

from $560 / night

$3920 - $22400 / week

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avg. 28 minutes

from $560 / night

(1) Excellent 

19

Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIALS: July 21-31 (=2 weekends!) at only 10k plus cleaning and pool heat (=10.75k Total) Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct …see more

from $350 / night

$1500 - $6601 / week

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Responds fast!
avg. 3 hours 41 minutes

from $350 / night

(6) Excellent 

24

Vacation home rental

Hamptons / Montauk

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
East Hampton Rental Registry #16185 *** Please see Summer 2017 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has …see more

from $575 / night

$3500 - $9000 / week

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from $575 / night

27

Hampton Bays Vacation home rental

Hamptons / 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 $522 / night

$500850 / week

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from $522 / night

(1) Excellent 

6

Vacation home in Westhampton

Hamptons / Westhampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Located on the bayside of Dune Road, this property is a beach lovers paradise. Walk across the street to one of the top 15 beaches in the country; fish, swim or boat on the bay just footsteps away; or just lounge on the large deck and enjoy a . sunset. The property fe …see more

from $191 / night

$975 - $2895 / week

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from $191 / 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

$2600 - $5900 / week

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from $370 / night

11

Vacation cottage with shared pool in Southampton

Hamptons / Southampton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Chic Sunny Private 2 bedrm Cottage (93 miles frm NYC) that step out on to your own secluded patio w/outdoor furniture + gas grill for easy BBQ meals. Cottage guests hv their own gate entry to the pool. You are minutes from World Famous Cooper's Beach, convenient to Vi …see more

from $350 / night

$2200 / week

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from $350 / night

(2) Excellent 

15

Vacation home in East Hampton

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spend your summer relaxing by the heated pool or enjoying the close beautiful bay beaches of the North West Woods or just a quick car ride to a sandy ocean beach of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. …see more

from $715 / night

$5000 - $7000 / week

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from $715 / night

6

Home rental in Sag Harbor

Hamptons / Sag Harbor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag …see more

from $350 / night

$2450 / week

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from $350 / night

(3) Excellent 

71

Vacation home in Hampton Bays

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for …see more

from $800 / night

$5500 - $6201 / week

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from $800 / night

(13) 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 $286 / night

$2000 - $5000 / week

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Responds fast!
avg. 3 hours 22 minutes

from $286 / night

15

Vacation home in Amagansett

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Beach house right on the sand, just a block away from a beautiful, uncrowded Atlantic Ocean beach. Clean and comfortable. Upstairs deck and downstairs patio off eat-in kitchen. Big living room, three bedrooms, two full bathrooms, washer and dryer, outdoor shower, gas gr …see more

from $500 / night

$1000 - $4250 / week

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from $500 / 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 $2143 / night

$15000 - $19000 / week

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Responds fast!
avg. 2 hours 40 minutes

from $2143 / 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 $1950 / night

$13500 / week

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Responds fast!
avg. 2 hours 15 minutes

from $1950 / 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

$3500 - $3900 / week

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from $500 / night

11

Vacation cottage rental

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedro …see more

from $286 / night

$2000 - $4000 / week

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from $286 / night

(1) Excellent 

29

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 5 mi
  • Child friendly
Very stylishly renovated on .60 acre, this East Hampton property features central air, 3 bedrooms and 2 baths. Great room with fireplace and lots of sunlight. Skylights in kitchen and living room. Top of the line Sub-zero refrigerator and wine storage. A chef's dream ki …see more

from $280 / night

$1960 - $2900 / week

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from $280 / night

7

Home rental in Bridgehampton

Hamptons / Bridgehampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
This cozy furnished country-style farmhouse sleeps ten people comfortably and is minutes to ocean or bay beaches, shopping, and restaurants. The house sits on over an acre of land adjacent to 1,000-acre Long Pond Reserve. Out back is a wooden deck, an in-ground pool, …see more

from $425 / night

$2975 / week

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from $425 / night

18

Water Mill Vacation home rental

Hamptons / Water Mill

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Our Southampton sunny beach luxury 4 bedroom home is ideally located near Southampton Village and area of farm fields, orchards, and wineries, and near to Coopers and Flying Point beaches. The home is set on a spacious property secluded by hedges and wildflower garden. …see more

from $1200 / night

$6000 - $10000 / week

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from $1200 / night

6

Vacation home in East Hampton

Hamptons / East Hampton

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This home has been fully renovated and has been meticulously furnished. 3 bedrooms and 2 modern bathrooms Modern eat in kitchen with butcher block counter & breakfast bar Sliding doors out to large backyard 1 queen bedroom 1 bedroom with 2 fulls 1 master suite with wet …see more

from $572 / night

$4000 - $5400 / week

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Responds fast!
avg. 3 hours 42 minutes

from $572 / night

(9) Excellent 

28

Vacation home in Hampton Bays

Hamptons / 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

$3000 / week

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from $400 / night

11

Amagansett Vacation home rental

Hamptons / Amagansett

4 8 21 nights min

  • 4 bedrooms
  • Sleeps 8
  • 21 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Our home, situated just north of the highway between East Hampton and Amagansett, is the ideal base for your family's vacation. The four-bedroom, four-bathroom house is bright and spacious. From the covered porch, you'll enter through the expansive living roo …see more

from $1143 / night

$8000 / week

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from $1143 / night

8

Amagansett Vacation home rental

Hamptons / Amagansett

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Amagansett Beach House sits directly on the most beautiful beach in the world. The main floor has 3 Bedrooms with decks to beach, 2 Full Baths, and laundry room. Upstairs is the Gourmet Kitchen, Dining & Living Areas, complete with Flat screen TV. Stunning deck overlook …see more

from $1786 / night

$12500 / week

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from $1786 / night

11

Vacation home in Westhampton

Hamptons / Westhampton

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
This 3 bedroom, 2 bath ranch house is in excellent condition and is newly furnished for comfort, style, and flexibility. Sitting on 1.5 acres the house is very secluded and private and just a short drive to West Hampton Beach and many beautiful beaches and parks. There …see more

from $450 / night

$2800 / week

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from $450 / 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 $750 / night

$4200 - $4900 / week

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Responds fast!
avg. 3 hours 2 minutes

from $750 / night

22

Home rental in East Quogue with swimming pool

Hamptons / East Quogue

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Four Bed, four bath. Great for two families. + .Nice pool, basketball hoop, bikes, bogie boards, beach chairs, croquet, badmition, x box in basement, pool table, outdoor speakers, nice bar b que, great lounges by pool, big back deck close to Southampton beaches, close i …see more

from $858 / night

$6000 / week

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from $858 / 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

$5000 / week

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from $680 / night

11

Vacation hotel apartment in Montauk

Hamptons / Montauk

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Situated on Montauk's most pristine stretch of oceanfront real estate, Gurney's Montauk Resort & Seawater Spa is a Hampton's icon and the only four-season resort in Montauk. With five unique dining and cocktail venues, guests can enjoy a wide range of dining options, fr …see more

from $715 / night

$4999 / week

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from $715 / night

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft …see more

from $3400 / night

$23800 / week

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Responds fast!
avg. 52 minutes

from $3400 / 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 $500 / night

$3500 - $10000 / week

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from $500 / night

18

East Hampton Vacation home rental

Hamptons / East Hampton

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • 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

$2000 - $6000 / week

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from $500 / night

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

$3000 / week

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from $600 / night

14

Southampton Vacation home rental

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Ask about pets
The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! Th …see more

from $434 / night

$3034 / week

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from $434 / night