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Southold Vacation Rentals
1-21 of 21 rentals

Minnehaha Marvel

$249 avg / night (excludes fees and taxes)
Southold, NY
3.0 (1)
1 Bedrooms | 2 Bath | Sleeps 4

Secret Garden Estate

$1,339 avg / night (excludes fees and taxes)
NEW!
Southold, NY
4 Bedrooms | 4 Bath | Sleeps 10

Watersedge Retreat

$702 avg / night (excludes fees and taxes)
NEW!
Southold, NY
3 Bedrooms | 2 Bath | Sleeps 6

Classic Southold Country Charmer

$157 avg / night (excludes fees and taxes)
Southold, NY
5.0 (2)
2 Bedrooms | 1 Bath | Sleeps 4

Cozy Greenport Cottage

$584 avg / night (excludes fees and taxes)
NEW!
Greenport, NY
5.0 (1)
3 Bedrooms | 2.5 Bath | Sleeps 10

Modern on 9th

$489 avg / night (excludes fees and taxes)
Greenport, NY
5.0 (3)
3 Bedrooms | 3 Bath | Sleeps 6

The Endless Summer Cottage

$275 avg / night (excludes fees and taxes)
NEW!
Cutchogue, NY
3 Bedrooms | 2 Bath | Sleeps 6

North Fork Waterfront Gem

$393 avg / night (excludes fees and taxes)
East Marion, NY
4.6 (5)
2 Bedrooms | 2 Bath | Sleeps 4

The Briar Patch

$325 avg / night (excludes fees and taxes)
NEW!
East Marion, NY
3 Bedrooms | 2 Bath | Sleeps 6

Serene Bay Breezes - Private Bay Beach Community

$517 avg / night (excludes fees and taxes)
NEW!
East Marion, NY
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

Villa Emilio

$968 avg / night (excludes fees and taxes)
NEW!
Orient, NY
4.0 (1)
3 Bedrooms | 1.5 Bath | Sleeps 6

Colonial Hampton Charm

$1,276 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
7 Bedrooms | 7 Bath | Sleeps 14

Southampton Beauty

$674 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
4 Bed | 3.5 Bath | Sleeps 9 (8 Adults Max)

Atterbury Estate

$677 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

Cedar Crest Retreat

$1,013 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
5 Bedrooms | 5.5 Bath | Sleeps 9

Contemporary Southampton Retreat

$544 avg / night (excludes fees and taxes)
Southampton, NY
5.0 (5)
2 Bedrooms | 2 Bath | Sleeps 4

Marble & Sun

$608 avg / night (excludes fees and taxes)
NEW!
Hampton Bays, NY
5 Bedrooms | 3 Bath | Sleeps 10

The Blissful Bay House

$1,211 avg / night (excludes fees and taxes)
Hampton Bays, NY
5.0 (4)
4 Bedrooms | 5 Bath | Sleeps 11

Hamptons Hideaway

$600 avg / night (excludes fees and taxes)
Hampton Bays, NY
4.0 (2)
4 Bedrooms | 3.5 Bath | Sleeps 10

Tranquil Bays Estate

$634 avg / night (excludes fees and taxes)
NEW!
Hampton Bays, NY
4 Bedrooms | 4.5 Bath | Sleeps 10

Accabonac Escape

$617 avg / night (excludes fees and taxes)
East Hampton, NY
5.0 (1)
2 Bed | 3.5 Bath | Sleeps 8 (6 Adults Max)
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