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Holiday Rentals in Hamptons

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672 rentals in Hamptons.
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3BR/2BA- Private Heated Pool Steps to Moriches Bay, holiday rental in Hamptons

3BR/2BA- Private Heated Pool Steps to Moriches Bay

3 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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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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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 9
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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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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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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MONTAUK CONDO RENOVATED 1 BEDROOM WATERFRONT ON FORT POND BAY, holiday rental in Hamptons

MONTAUK CONDO RENOVATED 1 BEDROOM WATERFRONT ON FORT POND BAY

1 bedroom
1 bathroom
Sleeps 5
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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Bay-View Architectural Masterpiece on Hog Creek, Watch Watercolor Sunsets..., holiday rental in Hamptons

Bay-View Architectural Masterpiece on Hog Creek, Watch Watercolor Sunsets...

6 bedrooms
7 bathrooms
Sleeps 11
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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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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Charming  A-Frame Home On Private Quiet Road, holiday rental in Hamptons

Charming A-Frame Home On Private Quiet Road

3 bedrooms
1 bathroom
Sleeps 6
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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WFH Cottage - Fast WiFi, holiday rental in Hamptons

WFH Cottage - Fast WiFi

1 bedroom
1 bathroom
Sleeps 4
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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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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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 6
Match: Sleeps
More info
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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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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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Ditch Plains Perfection- Walk to Beach, holiday rental in Hamptons

Ditch Plains Perfection- Walk to Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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Charming Classic Cottage, holiday rental in Hamptons

Charming Classic Cottage

2 bedrooms
2 bathrooms
Sleeps 4
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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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
More info
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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

4 bedrooms
3 bathrooms
Sleeps 8
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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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
More info
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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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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
More info
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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
More info
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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
More info
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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
More info
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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
More info
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Ditch Plains Beach Cottage- Walk to Beach, holiday rental in Hamptons

Ditch Plains Beach Cottage- Walk to Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Great Location Westhampton Short Walk to Village (1/2 mile), holiday rental in Hamptons

Great Location Westhampton Short Walk to Village (1/2 mile)

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

East Hampton Retreat

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Water Mill Getaway, holiday rental in Hamptons

Charming Water Mill Getaway

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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New Construction Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece., holiday rental in Hamptons

New Construction Southampton 6 BR, 6.5 Bath, 5 Fireplace Masterpiece.

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
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Sag Harbor Village walk to town and beach, holiday rental in Hamptons

Sag Harbor Village walk to town and beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Southampton Cottage | Prime Location, holiday rental in Hamptons

Modern Southampton Cottage | Prime Location

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stunning Shinnecock View, holiday rental in Hamptons

Stunning Shinnecock View

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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