50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
67 properties
Estates Southampton
52 properties
Vacation rentals Sag Harbor
28 properties
House rentals Montauk
22 properties
Apartments Hampton Bays
16 properties
House rentals Amagansett
12 properties
Apartments Water Mill
11 properties
Bridgehampton
11 properties
East Quogue
8 properties
Apartments Shelter Island
6 properties

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303 Vacation rentals

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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avg. 17 minutes

from $5,715 / night

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 $1,579 / night

$11,053 / week

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avg. 2 hours 30 minutes

from $1,579 / 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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Responds fast!
avg. 2 hours 35 minutes

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

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

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

14

Vacation private room with shared pool in Southampton

Hamptons / Southampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Air conditioning
Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the s …see more

from $175 / night

$1,225 / week

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avg. 37 minutes

from $175 / night

(3) Excellent 

17

Home rental in Quogue with tennis court

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Will your mom have to sit on the end of your futon with a plate of holiday goose and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the roast she bought doesn't fit in your oven? Well it is time to …see more

from $400 / night

$1,500 / week

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from $400 / night

30

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Nearest beach 0.001 mi
  • Child friendly
Resort style living in this fantastic private beachfront oasis in Sag Harbor Village. Enjoy fabulous views and amazing sunsets over Sag Harbor Bay from this wonderful 3 bedroom, 2.5 bath house with hot tub and sandy beach right in your backyard. Great family rental. K …see more

from $1,500 / night

$8,500 / week

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from $1,500 / night

(1) Excellent 

9

Vacation home in Westhampton

Hamptons / Westhampton

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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 $190 / night

$975 / week

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from $190 / 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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Responds fast!
avg. 3 hours 40 minutes

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

11

Home rental in East Quogue

Hamptons / East Quogue

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This 4 bedroom, 2 bathroom contemporary is just steps away from a private beach and marina. Some amenities include: New granite kitchen Cathedral great room with flat screen tv Hardwood floors Multi level decking In ground heated pool Patio furnitur …see more

from $500 / night

$3,500 / week

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from $500 / 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

$4,000 - $5,400 / week

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avg. 3 hours 42 minutes

from $572 / 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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avg. 2 hours 51 minutes

from $2,429 / night

11

Home rental in East Hampton with swimming pool

Hamptons / East Hampton

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This 5 bedroom has been added on and renovated throughout the years, and is bright and sunny with high ceilings and large window in the living room. Through the front door you will find a spacious living room, with wood burning fireplace and dining area to enjoy large …see more

from $750 / night

$5,250 / week

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from $750 / 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 $249 / night

$999 - $4,999 / week

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Responds fast!
avg. 2 hours 58 minutes

from $249 / 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

$5,000 / week

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from $715 / 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

$2,800 / week

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from $450 / night

37

Vacation home in Southampton

Hamptons / Southampton

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. …see more

from $975 / night

$6,000 - $8,100 / week

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avg. 3 hours 26 minutes

from $975 / 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 - $5,000 / week

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avg. 3 hours 38 minutes

from $358 / 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 - $10,500 / week

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avg. 14 minutes

from $849 / 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 $3,300 / night

$15,900 - $19,900 / week

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Responds fast!
avg. 1 hour 26 minutes

from $3,300 / 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 $655 / night

$4,585 / week

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from $655 / night

14

Hampton Bays Vacation home rental

Hamptons / Hampton Bays

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Your own private summer resort. This house has it alll, you won't want to leave! Waterfront dock, jacuzzi, sparkling pool, multiple patios, 2 outdoor grills, and multiple balconies are key outdoor features. State of the art kitchen, large country dining room table, 2 f …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

29

Vacation apartment in East Quogue

Hamptons / East Quogue

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Pet friendly
This is a very cozy house with lots of trees around. Only 7 minute drive to the beach. The house has Two bedrooms, one queen bed in the master bedroom, a trundle bed in the second bedroom. Also a comfortable sofa bed in the living room. There is plenty of space in the b …see more

from $265 / night

$1,750 / week

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avg. 1 hour 20 minutes

from $265 / night

(1)  

24

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Let this stunning 3-bedroom, 2-bathroom vacation rental home jump start your East Hampton retreat! Offering fantastic amenities, accommodations for 6 and an unbeatable location near East Harbor, this unit leaves little to be desired! THE PROPERTY From the moment you a …see more

from $275 / night

$1,650 - $3,900 / week

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Responds fast!
avg. 14 minutes

from $275 / night

(2) Very Good 

10

Vacation home in East Hampton

Hamptons / East Hampton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Air conditioning
  • Private garden
This 2 story home with 3 bedrooms and 2 baths contains a master bedroom with ensuite bathroom. It's a relaxing, quiet atmosphere. Located just 5 minutes from the town and 5 minutes from the beach. Newly furnished house is a perfect summer getaway. Naturally well lit wit …see more

from $325 / night

$2,000 / week

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from $325 / night

(1) Good 

5

Vacation condo in Montauk

Hamptons / Montauk

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Royal Atlantic Beach Front Resort , Montauk 1 Bedroom Suite For Rent Minimum of 2 Night Stay Sleeps 4 126 S Emerson Ave, Montauk, NY 11954 ONE BEDROOM VIP SUITE: Located directly across the street from the beach. It has a private balcony facing the pool courtyard. …see more

from $200 / night

$1,400 / week

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from $200 / night

18

Home rental in Montauk

Hamptons / Montauk

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The professionally styled, newly renovated/furnished upside down house is on a private wooded acre with ocean views from the living areas and is one block to ocean beach and Gurney’s. The open living/dining/kitchen and master bedroom suite are on the top floor. An add …see more

from $2,000 / night

$14,000 / week

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avg. 1 hour 13 minutes

from $2,000 / night

23

Vacation home in Hampton Bays

Hamptons / Hampton Bays

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Waterfront Home on Shinnecock Bay, on one of the nicest private streets in Hampton Bays, you will have use of the 2 kayaks on the bay, beautiful sunsets, and a mile away from the ocean beaches on Dune Road. We are about 2 miles from town. Great little cafe/market wal …see more

from $995 / night

$5,900 / week

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Responds fast!
avg. 1 hour 26 minutes

from $995 / 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: Please contact us for 2+ week early Bird specials. 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 access to the pool and outdoor …see more

from $300 / night

$1,500 - $6,700 / week

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from $300 / 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

12

Vacation home with golf nearby in Montauk

Hamptons / Montauk

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This Is a smartly furnished, relaxing house close to everything that beautiful Montauk has to offer. We just purchased the house In April 2015 and did an extensive renovation... new bathrooms, new floors, new A/C, painted, and new appliances. The house Is warm and relax …see more

from $750 / night

$2,500 - $7,500 / week

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from $750 / night

8

Vacation hotel apartment in Westhampton

Hamptons / Westhampton

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • 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 $140 / night

$700 - $1,150 / week

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from $140 / 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

$3,000 / week

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from $400 / 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

(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 $350 / night

$1,960 - $2,900 / week

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from $350 / night

(1) Excellent 

19

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end "tanning bed", great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an …see more

from $1,200 / night

$11,000 / week

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Responds fast!
avg. 3 hours 41 minutes

from $1,200 / 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