50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
77 properties
Estates Southampton
36 properties
Vacation rentals Sag Harbor
34 properties
House rentals Montauk
25 properties
Apartments Hampton Bays
15 properties
Bridgehampton
11 properties
House rentals Amagansett
11 properties
East Quogue
11 properties
Apartments Water Mill
10 properties
Quogue
5 properties

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245 Vacation rentals

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

21

Home rental in East Hampton

Hamptons / East Hampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Lovely cedar shingled home with immaculate gardens. A short walk or bike to Gardiner's Bay and Clearwater Beach. Enjoy the heated swimming pool, fire pit or hot tub. The house is in excellent condition with 4 brs, 3.5 baths and additional bedroom space in the finished b …see more

from $858 / night

$6000 / week

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from $858 / 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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from $900 / night

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 $1500 / night

$10000 - $12000 / week

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from $1500 / 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 $7143 / night

$50000 / week

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from $7143 / 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

19

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $351 / night

$1500 - $6600 / week

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from $351 / night

24

Hamptons / Sag Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning

from $449 / night

$3000 - $6293 / week

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from $449 / night

11

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

from $215 / night

$1500 - $4000 / week

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from $215 / night

(13) Excellent 

24

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

from $286 / night

$2000 - $5000 / week

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from $286 / night

18

Hamptons / Montauk

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

from $500 / night

$3000 - $6000 / week

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from $500 / night

12

Riverhead / Aquebogue

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly

from $400 / night

$1500 - $2700 / week

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from $400 / night

(4) Excellent 

28

Hamptons / Sag Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

from $2143 / night

$15000 / week

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from $2143 / night

23

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly

from $751 / night

$4200 - $4900 / week

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from $751 / night

(6) Excellent 

24

Hamptons / Montauk

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

from $576 / night

$3500 - $9000 / week

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from $576 / night

(9) Excellent 

28

Hamptons / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly

from $400 / night

$3000 / week

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from $400 / night

28

Hamptons / Hampton Bays

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $400 / night

$2800 / week

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from $400 / night

(1) Excellent 

14

Hamptons / Shelter Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning

from $268 / night

$1296 - $5000 / week

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from $268 / night

(3) Excellent 

71

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool

from $800 / night

$5500 - $6200 / week

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from $800 / night

23

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $2751 / night

$17000 - $27500 / week

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from $2751 / night

(3) Excellent 

11

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+

from $251 / night

$1500 - $2551 / week

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from $251 / night

28

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from $749 / night

$4120 - $8751 / week

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from $749 / night

(4) Excellent 

21

Hamptons / Sag Harbor

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $496 / night

$2600 - $2951 / week

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from $496 / night

27

Hamptons / Hampton Bays

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $572 / night

$360260 - $500850 / week

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from $572 / night

9

Hamptons / Montauk

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $359 / night

$2507 / week

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from $359 / night

(2) Excellent 

14

Hamptons / Sag Harbor

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+

from $451 / night

$3000 - $4576 / week

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from $451 / night

(1) Good 

5

Hamptons / Montauk

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $351 / night

$2451 / week

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from $351 / night

24

Hamptons / Amagansett

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $800 / night

$4800 - $6200 / week

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from $800 / night

22

Hamptons / Bridgehampton

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $1008 / night

$7056 / week

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from $1008 / night

(2) Excellent 

17

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

from $400 / night

$2500 / week

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from $400 / night

13

Hamptons / Montauk

3 8 14 nights min

  • 3 bedrooms
  • Sleeps 8
  • 14 nights min
  • Child friendly
  • Air conditioning

from $286 / night

$2000 - $5500 / week

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from $286 / night

11

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets

from $600 / night

$3000 / week

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from $600 / night

50

Hamptons / Southampton

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

from $1100 / night

$6500 - $8600 / week

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from $1100 / night

(2) Excellent 

18

Hamptons / East Hampton

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $1500 / night

$10500 / week

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from $1500 / night

20

Hamptons / Shelter Island

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

from $389 / night

$2700 / week

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from $389 / night

38

Hamptons / Amagansett

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $900 / night

$6300 / week

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from $900 / night

13

Hamptons / Bridgehampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

from $1000 / night

$7000 - $7500 / week

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from $1000 / night

22

Hamptons / East Hampton

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $1300 / night

$10000 / week

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from $1300 / night

(1) Very Good 

16

Hamptons / Hampton Bays

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from $285 / night

$1995 / week

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from $285 / night

19

Hamptons / Southampton

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Ask about pets

from $1500 / night

$10500 / week

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from $1500 / night

1