Southold Vacation Home Rentals, Treehouses & more


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Areas near Southold

Travelers going to Southold are booking August dates now. Secure your vacation rental today and have the perfect trip.

Great rentals within 20 miles that match your search

1 / 7

Beautiful Bridgehampton Home

  • 5
  • 10
  • Min stay varies

$425

Details

1 / 19

5 Min to Bridgehampton n Sag Harbor 8 Min Ocean

  • 4
  • 9
  • 2 nights min

$1750

Details

1 / 20

Very Private and Tranquil House in wooded estate.

  • 4
  • 8
  • 7 nights min

$639

Details

1 / 5

Sophisticated Village Home - Serene Setting - Lovely Pool and Garden

  • 2
  • 6
  • Min stay varies

$572

Details

1 / 11

Amagansett House with Pool near Village & Beach

  • 4
  • 8
  • 21 nights min

$1144

Details

1 / 18

Villa Elise - Modern Hamptons Villa Fit for GQ

  • 4
  • 12
  • 7 nights min

$1400

Details

1 / 11

Spectacular East Hampton Mansion

  • 8
  • 20
  • 7 nights min

$5714

Details

1 / 28

Elegant Designer Hamptons Retreat in Sag Harbor

  • 5
  • 12
  • Min stay varies

$2143

Details

1 / 14

North Fork House with Private Beach Access

  • 4
  • 8
  • 7 nights min

$300

Details

1 / 20

Beautiful Estate home in the Hamptons, New York

  • 7
  • 10
  • 14 nights min

$2836

Details

1 / 22

Mini Resort in East Hampton on a private acre

  • 3
  • 6
  • 14 nights min

$357

Details

1 / 9

Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!

  • 2
  • 6
  • 2 nights min

$389

Details

1 / 22

Southampton Guest House Suite

  • 1
  • 4
  • Min stay varies

$226

Details

1 / 6

East Hampton Home 2 blocks from Beach

  • 3
  • 10
  • 7 nights min

$621

Details

1 / 21

Designer Decorated 3 Bedroom in Prime Location Heated Salt Water Pool

  • 3
  • 8
  • 2 nights min

$401

Details

1 / 15

Modern 3 Bedroom 2 Bath Waterfront House with Private Beach!

  • 3
  • 6
  • 14 nights min

$470

Details

1 / 17

New Availability for August.... 2 to 4 weeks available.

  • 4
  • 8
  • 1 night min

$401

Details

1 / 24

Westhampton Beach 4/5Br New Construction

  • 5
  • 12
  • 21 nights min

$851

Details

1 / 13

Hampton Classic- Pet Friendly

  • 4
  • 8
  • 5 nights min

$844

Details

1 / 123

The Graybarn Cottage in the Heart of East Hampton

  • 4
  • 12
  • Min stay varies

$1712

Details

1 / 17

Relaxing Retreat in Hampton Bays

  • 4
  • 8
  • Min stay varies

$447

Details

1 / 8

Greenport Village Walking Distance to All

  • 2
  • 4
  • 7 nights min

$397

Details

1 / 11

East Hampton Summer Rental

  • 4
  • 8
  • 1 night min

$501

Details

1 / 13

North Fork Loft - Perfect for Wine & Food Weekends

  • 5
  • 14
  • Min stay varies

$895

Details

1 / 12

New Construction Estate In Georgica Pond EHampton

  • 8
  • 18
  • 7 nights min

$7500

Details

1 / 21

White glove, private, romantic with waterview

  • 3
  • 6
  • 7 nights min

$894

Details

1 / 29

Private 6BR /Sag Harbor Southampton Home w Pool & Jacuzzi

  • 6
  • 12
  • Min stay varies

$889

Details

1 / 6

Beach house dune rd

  • 3
  • 6
  • 7 nights min

$986

Details

1 / 25

Waterfront North Fork Sunny Home

  • 3
  • 6
  • Min stay varies

$295

Details

1 / 5

Lakeside Cottage, Walk to Beach. Beautiful Sunsets

  • 2
  • 4
  • 14 nights min

$300

Details

1 / 14

Southold Beach House - The Lighthouse Cottage

  • 2
  • 5
  • 14 nights min

$357

Details

1 / 18

North Fork Beach Bungalow

  • 5
  • 10
  • 14 nights min

$501

Details

1 / 15

Southold Summer Home for rent

  • 3
  • 6
  • 7 nights min

$465

Details

1 / 11

Peaceful North Fork Escape - Special Spring and Summer Rates

  • 3
  • 5
  • 14 nights min

$250

Details

1 / 16

Beach House In Wine Country; Huge Sun Room

  • 2
  • 4
  • Min stay varies

$326

Details

1 / 24

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

  • 5
  • 14
  • Min stay varies

$496

Details

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