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.

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1 / 25

Waterfront North Fork Sunny Home

  • 3
  • 6
  • Min stay varies

$295

Details

2
1 / 17

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

  • 3
  • 6
  • 14 nights min

$375

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

$500

Details

9
1 / 23

Adorable, Renovated 1890's Farmhouse... Walk to Beaches & Town!

  • 3
  • 6
  • 7 nights min

$186

Details

1 / 18

North Fork Beach Bungalow

  • 5
  • 10
  • 14 nights min

$500

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

2
1 / 16

Beach House In Wine Country; Huge Sun Room

  • 2
  • 4
  • Min stay varies

$325

Details

1 / 24

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

  • 5
  • 14
  • Min stay varies

$495

Details

Great rentals within 30 miles that match your search

1 / 14

North Fork Beach House on LI Sound

  • 3
  • 6
  • 14 nights min

$429

Details

10
1 / 31

->HAMPTONS - Shelter Island 4+Bdrm Euro Beach Home

  • 4
  • 10
  • Min stay varies

$325

Details

7
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>>> ROMANTIC Beach Getaway! Seclusion, Waterfalls

  • 2
  • 6
  • Min stay varies

$395

Details

33
1 / 9

Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!

  • 2
  • 6
  • 2 nights min

$389

Details

7
1 / 14

Waterfront Condo C204 at The Cliffside Resort

  • 2
  • 6
  • 2 nights min

$300

Details

1 / 25

Fabulous Beach Getaway

  • 3
  • 6
  • 7 nights min

$643

Details

1 / 19

Waterfront Charmer on idyllic Shelter Island

  • 3
  • 8
  • 14 nights min

$929

Details

1
1 / 10

The Farmhouse

  • 5
  • 14
  • Min stay varies

$600

Details

1 / 14

North Fork Long Island Wine Country Cottage, Water Views

  • 2
  • 6
  • Min stay varies

$275

Details

1 / 25

The Captain's House

  • 3
  • 8
  • Min stay varies

$225

Details

24
1 / 13

New North Fork Beach Condo, Pool, Resort, Heart of the Wineries

  • 2
  • 6
  • 2 nights min

$309

Details

3
1 / 23

Family and Friends in Greenport

  • 4
  • 10
  • 2 nights min

$300

Details

1 / 22

Historic Greenport Walk to Town

  • 4
  • 9
  • Min stay varies

$700

Details

9
1 / 18

Cutchogue Beach Cottage

  • 2
  • 6
  • 14 nights min

$150

Details

1 / 19

Victorian Seasons Stirling

  • 5
  • 9
  • 1 night min

$850

Details

1 / 18

Architect Designed Home in Waterfront Village

  • 2
  • 4
  • 6 nights min

$357

Details

1 / 8

Greenport Village Walking Distance to All

  • 2
  • 4
  • 7 nights min

$400

Details

1 / 16

Greenport Village Home Walking Distance to All

  • 3
  • 8
  • 30 nights min

$517

Details

1
1 / 22

Sunshine Bungalow Shelter Island Retreat

  • 2
  • 6
  • Min stay varies

$400

Details

1 / 30

NEW! Greenport Studio Apt - Downtown Location!

  • 1
  • 2
  • Min stay varies

$155

Details

1 / 26

NEW! 1BR Greenport Apartment - Recently Remodeled!

  • 1
  • 2
  • Min stay varies

$185

Details

1 / 26

NEW! 2BR Greenport Apartment - Heart of Downtown!

  • 2
  • 4
  • Min stay varies

$285

Details

1 / 16

Historic Cottage Near Beach!

  • 2
  • 4
  • Min stay varies

$234

Details

1 / 13

Remodeled Greenport Farmhouse

  • 3
  • 6
  • 14 nights min

$425

Details

1 / 21

Renovated North Fork Home Close to Beach& Wineries

  • 4
  • 8
  • 14 nights min

$343

Details

1
1 / 14

Exquisite Waterfront Estate on Shelter Island NY; 100 Foot Dock; Beaches, Town

  • 4
  • 8
  • Min stay varies

$267

Details

1
1 / 20

North Fork Beach Cottage in New Suffolk

  • 2
  • 5
  • 14 nights min

$495

Details

4
1 / 14

North Fork House with Private Beach Access

  • 4
  • 8
  • 7 nights min

$299

Details

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