50 Best Hamptons House rentals on Holiday Lettings - Apartments

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351 Vacation rentals

29

Vacation home with swimming pool in Hampton Bays

Southampton / Hampton Bays

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
For adults over 26 years please kids OK INQUIRE first with your details for availability min. 3 nights July 8-Labor D and 4 nights July 4th week-end. EXTRA at CHECK- IN: 180$ cleaning fee/stay ,refundable security deposit 500$-3.5K (depend dates,number of guests and a …see more

from $687 / night

$4,580 - $7,091 / week

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from $687 / 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 $1,031 / night

$6,870 / week

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from $1,031 / 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 $6,543 / night

$45,800 / week

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avg. 17 minutes

from $6,543 / 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 $382 / night

$2,672 / week

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from $382 / 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 $1,145 / night

$8,015 / week

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from $1,145 / 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 $516 / night

$3,206 / week

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from $516 / 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 $516 / night

$3,206 / week

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from $516 / 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 $973 / night

$6,805 / week

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avg. 9 minutes

from $973 / night

29

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • 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 8 guests! This home boasts one of the best locations with walking access to pri …see more

from $859 / night

$6,012 / week

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Responds fast!
avg. 9 minutes

from $859 / night

(1) Excellent 

25

Vacation home in Hampton Bays

Southampton / Hampton Bays

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Whether you're visiting on spring break, Christmas holiday, a quick summer getaway, this 3-bedroom, 2.5-bath Hampton's house is the place to be! This home features space for 7, eclectic mid-century modern furnishings, and a spacious backyard. Walk to Shinnecock Bay and …see more

from $287 / night

$2,004 / week

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Responds fast!
avg. 9 minutes

from $287 / 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 $573 / night

$4,008 / week

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from $573 / night

41

Vacation home in Montauk

Hamptons / Montauk

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • 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 $687 / night

$4,809 / week

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from $687 / night

28

Water Mill Vacation home rental

Hamptons / Water Mill

6 12 5 nights min

  • 6 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Exquisite 50 foot driveway, handmade iron gated property, affording total privacy, 2 acres exquisite landscaping, flowers, vegetable garden, 2 waterfalls, gardens, stream, pond, pond beach, 30 x 40 gunite swimming pool with Rose Arbor, fruit orchard, Outdoor Kitchen & …see more

from $1,145 / night

$8,015 / week

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from $1,145 / night

25

Vacation home in Westhampton Beach

Hamptons / Westhampton Beach

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Located in Westhampton Beach in the community of West Hampton Dunes- this beach bungalow on the Bay has direct access to the Bay and Ocean. 3 Bedrooms, 1 full bath and private double outdoor shower. 3 Bedrooms- 1 queen size bed, 1 full size bed and 2 bunk beds (4 sing …see more

from $630 / night

$4,580 / week

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from $630 / night

24

Home rental in Amagansett with swimming pool

Hamptons / Amagansett

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Heading to the Hamptons? Then go ahead and book this 6-bedroom, 5.5-bathroom vacation rental home in Amagansett with sleeping for 12! Great for larger families, friends, or couples seeking a beach getaway, this will serve as the perfect home base for all of your adventu …see more

from $848 / night

$5,931 / week

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avg. 9 minutes

from $848 / 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 $859 / night

$6,012 / week

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from $859 / night

24

Vacation cottage with swimming pool in Shelter Island Heights

Shelter Island / Shelter Island Heights

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer …see more

from $441 / night

$3,086 / week

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avg. 9 minutes

from $441 / night

(3) Excellent 

19

Vacation home in Westhampton Beach

Hamptons / Westhampton Beach

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the bay side of Dune Road on a scenic peninsula and surrounded by water, this contemporary is a beach lovers paradise. It's a short walk to the great Westhampton Beach, one of the top 15 ocean beaches in the country; a 5 minute drive to the village; or you ca …see more

from $205 / night

$1,117 - $1,546 / week

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from $205 / 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 $401 / night

$1,718 - $7,443 / week

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from $401 / 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 $2,061 / night

$10,305 / week

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Responds fast!
avg. 3 hours 3 minutes

from $2,061 / night

(1) Excellent 

6

East Hampton Vacation home rental

Hamptons / East Hampton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Air conditioning
Superbly designed by its owners, this dwelling boasts the elegance and sobriety of a minimalist painting. Yet, it remains very warm and inviting. The house sits on a wooded acre, across the road from a 140 acre reserve. The 2,500 sq. ft. space offers 2 bedrooms, 2 bath …see more

from $287 / night

$2,004 - $5,725 / week

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from $287 / 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 $573 / night

$2,290 / week

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from $573 / night

24

Montauk Vacation home rental

Hamptons / Montauk

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Open floorplan newly renovated close to ocean, bay beaches and montauk downs golf course 1st flr: family TV room 2 bedrooms - 2 sets of bunk beds & queen bed 1 bath w/ soaking tub 2nd flr: Open kitchen/living out to deck, 2 bedrooms - 1 king bed & 1 queen bed 1 bath …see more

from $1,145 / night

$8,015 / week

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from $1,145 / 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 $655 / night

$4,580 / week

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from $655 / 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 $745 / night

$4,008 / week

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from $745 / 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 $655 / night

$4,580 - $6,183 / week

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from $655 / 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 $695 / night

$4,866 / week

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from $695 / night

24

Vacation cottage in Springs

Hamptons / Springs

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Spend a serene weekend with friends at this beautifully appointed 2-bed, 1-bath vacation rental cottage in East Hampton, NY. The home has an idyllic nature to it thanks to the shingle-style architecture, multiple outdoor seating areas, English-style flower garden with f …see more

from $401 / night

$2,806 / week

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Responds fast!
avg. 9 minutes

from $401 / 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 $630 / night

$4,008 / week

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from $630 / night

(3)  

15

Vacation home in Westhampton Beach

Hamptons / Westhampton Beach

5 13 3 nights min

  • 5 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Beautiful home secluded area. Just renovated. Near everything ocean and beaches. Big backyard. Sports play. Outdoor kitchen-Pool-outdoor shower-circular driveway-6 cars parking. Huge kitchen island and bar sink. 3 masters suites second floor. 3 others large sizes 1st f …see more

from $172 / night

$1,718 - $10,534 / week

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from $172 / 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 $1,374 / night

$9,618 / week

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from $1,374 / night

(1) Excellent 

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • 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 $4,122 / night

$28,854 / week

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Responds fast!
avg. 1 hour 38 minutes

from $4,122 / 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 $779 / night

$5,725 / week

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from $779 / night

(3) Very Good 

21

Vacation home in Remsenburg

Hamptons / Remsenburg

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Easy summer living at this bright contemporary ranch located steps from Moriches bay in Westhampton/Remsenburg. Open kitchen- dining area, living room with fireplace, 3 bedrooms, 2 baths, central air conditioning, and a private yard with a heated swimming pool. …see more

from $475 / night

$3,321 / week

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from $475 / night

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.Th …see more

from $573 / night

$3,435 / week

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from $573 / night

19

Home rental in Amagansett

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
3 Bedrooms, 3 Bathroom, Sleeps 6+2 with A/C & HOTTUB Rental Registry # 16-2027 The Beach House is located in the Amagansett Dunes in the famous Hampton's and sits directly across the way from the most beautiful beach in the world. The main floor has 3 Bedrooms 2 Full B …see more

from $900 / night

$6,298 / week

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from $900 / night

46

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 10 14 nights min

  • 4 bedrooms
  • sleeps 10
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the w …see more

from $785 / night

$5,491 / week

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from $785 / night

(2) Excellent 

30

Shelter Island Vacation home rental

Hamptons / Shelter Island

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • 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 $338 / night

$1,483 - $5,725 / week

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from $338 / 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 $573 / night

$4,008 / week

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from $573 / 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 $1,309 / night

$9,160 / week

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from $1,309 / night

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