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Hamptons Holiday Rentals

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623 rentals in Hamptons.
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Ocean Front Cottage Montauk for rent, holiday rental in Hamptons

Ocean Front Cottage Montauk for rent

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach House W/Short Walk to Ditch Plains Beach, holiday rental in Hamptons

Beach House W/Short Walk to Ditch Plains Beach

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW HOUSE, 6Bd, 5bth, 4200sqft, Heated Pool OPEN, Traffic Free, Gigabit Internet, holiday rental in Hamptons

NEW HOUSE, 6Bd, 5bth, 4200sqft, Heated Pool OPEN, Traffic Free, Gigabit Internet

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Hampton Bays, south of 27A, holiday rental in Hamptons

Hampton Bays, south of 27A

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hip & Stylish East Hampton Getaway, holiday rental in Hamptons

Hip & Stylish East Hampton Getaway

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southampton House Perfect for Families and Entertaining, holiday rental in Hamptons

Southampton House Perfect for Families and Entertaining

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming studio cottage between village and ocean. The perfect Hamptons escape, holiday rental in Hamptons

Charming studio cottage between village and ocean. The perfect Hamptons escape

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly renovated! Quiet, private, short walk to the beach., holiday rental in Hamptons

Newly renovated! Quiet, private, short walk to the beach.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Cottage Perfection, holiday rental in Hamptons

Waterfront Cottage Perfection

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful North Fork Vacation Home - Wineries, Beaches, Waterpark, Dining., holiday rental in Hamptons

Beautiful North Fork Vacation Home - Wineries, Beaches, Waterpark, Dining.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Southampton Village Clean Renovated Sun Filled Charm,  Gunite Heated Salt Pool, holiday rental in Hamptons

Southampton Village Clean Renovated Sun Filled Charm, Gunite Heated Salt Pool

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hamptons Cousy, Spacious, Family Home by the beach, holiday rental in Hamptons

Hamptons Cousy, Spacious, Family Home by the beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Southampton House South of Highway Perfect for Families, holiday rental in Hamptons

Southampton House South of Highway Perfect for Families

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Adorable Cottage Home In Beautiful East Hampton, holiday rental in Hamptons

Adorable Cottage Home In Beautiful East Hampton

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Backyard Sanctuary.  Close to beach, harbor, golf.    Perfect family getaway., holiday rental in Hamptons

Backyard Sanctuary. Close to beach, harbor, golf. Perfect family getaway.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Huge Children’s Playground Set, swings and Fenced-in and Heated Pool!, holiday rental in Hamptons

Huge Children’s Playground Set, swings and Fenced-in and Heated Pool!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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East Hampton Village:  Beautifully Renovated 3 Br Classic Cottage Walk To All, holiday rental in Hamptons

East Hampton Village: Beautifully Renovated 3 Br Classic Cottage Walk To All

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Home in Secluded Wooded Area 10 mins from East Hampton Village, holiday rental in Hamptons

Gorgeous Home in Secluded Wooded Area 10 mins from East Hampton Village

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Relax in Hampton Bays..., holiday rental in Hamptons

Relax in Hampton Bays...

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Hampton Holiday Family Fantasy for your Team of TEN, holiday rental in Hamptons

Stunning Hampton Holiday Family Fantasy for your Team of TEN

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront hidden gem with dock, holiday rental in Hamptons

Waterfront hidden gem with dock

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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3 bedroom Hamptons home near beach, vineyards, shopping, golf, holiday rental in Hamptons

3 bedroom Hamptons home near beach, vineyards, shopping, golf

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dune Rd's Pond Pt Peninsula Westhampton Beach Bay Views Walk to Ocean Beach 3BRM, holiday rental in Hamptons

Dune Rd's Pond Pt Peninsula Westhampton Beach Bay Views Walk to Ocean Beach 3BRM

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Eagles Nest - Private Hamptons Retreat by Beaches and Vineyards, holiday rental in Hamptons

Eagles Nest - Private Hamptons Retreat by Beaches and Vineyards

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Montauk Surf Club Oceanside Resort Condominium, holiday rental in Hamptons

Montauk Surf Club Oceanside Resort Condominium

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, Newly Renovated Bridgehampton Home, holiday rental in Hamptons

Beautiful, Newly Renovated Bridgehampton Home

4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sag Harbor, Hamptons Hideaway, holiday rental in Hamptons

Sag Harbor, Hamptons Hideaway

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ditch Plains Perfection- Walk to Beach, holiday rental in Hamptons

Ditch Plains Perfection- Walk to Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town, holiday rental in Hamptons

Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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WFH Cottage - Fast WiFi, holiday rental in Hamptons

WFH Cottage - Fast WiFi

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Brand New Luxury 6-br In East Hampton With Amazing Outdoor Space, holiday rental in Hamptons

Brand New Luxury 6-br In East Hampton With Amazing Outdoor Space

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Montauk Condo ~ Stunning Sunsets & the Sea at Your Doorstep, holiday rental in Hamptons

Montauk Condo ~ Stunning Sunsets & the Sea at Your Doorstep

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Montauk Setting; Walk to Beach & Town; Large Pool; Jacuzzi; Kid Friendly, holiday rental in Hamptons

Private Montauk Setting; Walk to Beach & Town; Large Pool; Jacuzzi; Kid Friendly

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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*SAIL* YOUR OWN PRIVATE YACHT !  DAYSAILS ON HAMPTONS  #1 CATAMARAN, holiday rental in Hamptons

*SAIL* YOUR OWN PRIVATE YACHT ! DAYSAILS ON HAMPTONS #1 CATAMARAN

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Secluded Beachfront Home with Private Beach--Available for Summer, holiday rental in Hamptons

Secluded Beachfront Home with Private Beach--Available for Summer

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Hamptons Vacation Home With Heated Pool, Hot Tub & Brand New Tennis Court, holiday rental in Hamptons

Luxury Hamptons Vacation Home With Heated Pool, Hot Tub & Brand New Tennis Court

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Flexible Cancellation-Book with Confidence!, holiday rental in Hamptons

Flexible Cancellation-Book with Confidence!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Book your vacation at our EH retreat on the water!, holiday rental in Hamptons

Book your vacation at our EH retreat on the water!

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Twin Pond Ocean Front Cottage with Beach Pass, holiday rental in Hamptons

Twin Pond Ocean Front Cottage with Beach Pass

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Hamptons Paradise (Rental Registry #16-1225), holiday rental in Hamptons

Private Hamptons Paradise (Rental Registry #16-1225)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family-friendly house, large heated pool, landscape gardens, near private beach, holiday rental in Hamptons

Family-friendly house, large heated pool, landscape gardens, near private beach

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!, holiday rental in Hamptons

Gorgeous, Private, Water View New Home! New Pool and Hot Tub- Bay 1 Street away!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Dream Home, holiday rental in Hamptons

Beautiful Dream Home

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Updated Modern Waterfront condo with private beach, pool, tennis, pier & more., holiday rental in Hamptons

Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 4B/3Bth East Hampton Shingled Classic With Pool: Perfect For Families, holiday rental in Hamptons

Charming 4B/3Bth East Hampton Shingled Classic With Pool: Perfect For Families

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Ditch Plains Beach House- Walk to Beach, holiday rental in Hamptons

Gorgeous Ditch Plains Beach House- Walk to Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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East Hampton Retreat, holiday rental in Hamptons

East Hampton Retreat

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming, Renovated Island Cottage - Shelter Island License #:  ********, holiday rental in Hamptons

Charming, Renovated Island Cottage - Shelter Island License #: ********

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town, holiday rental in Hamptons

Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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