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Southold Vacation Rentals
1-19 of 19 rentals

Minnehaha Marvel

$251 avg / night (excludes fees and taxes)
Southold, NY
3.0 (1)
1 Bedrooms | 2 Bath | Sleeps 4

Watersedge Retreat

$691 avg / night (excludes fees and taxes)
NEW!
Southold, NY
3 Bedrooms | 2 Bath | Sleeps 6

Classic Southold Country Charmer

$147 avg / night (excludes fees and taxes)
Southold, NY
5.0 (2)
2 Bedrooms | 1 Bath | Sleeps 4

Cozy Greenport Cottage

$621 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

$278 avg / night (excludes fees and taxes)
NEW!
Cutchogue, NY
3 Bedrooms | 2 Bath | Sleeps 6

North Fork Waterfront Gem

$377 avg / night (excludes fees and taxes)
East Marion, NY
4.6 (5)
2 Bedrooms | 2 Bath | Sleeps 4

The Briar Patch

$314 avg / night (excludes fees and taxes)
NEW!
East Marion, NY
3 Bedrooms | 2 Bath | Sleeps 6

Serene Bay Breezes - Private Bay Beach Community

$487 avg / night (excludes fees and taxes)
NEW!
East Marion, NY
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

Villa Emilio

$971 avg / night (excludes fees and taxes)
NEW!
Orient, NY
4.0 (1)
3 Bedrooms | 1.5 Bath | Sleeps 6

Atterbury Estate

$641 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
5.0 (1)
4 Bedrooms | 3 Bath | Sleeps 8

Contemporary Southampton Retreat

$537 avg / night (excludes fees and taxes)
Southampton, NY
5.0 (5)
2 Bedrooms | 2 Bath | Sleeps 4

Southampton Beauty

$702 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
4 Bed | 3.5 Bath | Sleeps 9 (8 Adults Max)

Colonial Hampton Charm

$1,275 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
7 Bedrooms | 7 Bath | Sleeps 14

Cedar Crest Retreat

$984 avg / night (excludes fees and taxes)
NEW!
Southampton, NY
5 Bedrooms | 5.5 Bath | Sleeps 9

Marble & Sun

$601 avg / night (excludes fees and taxes)
NEW!
Hampton Bays, NY
5 Bedrooms | 3 Bath | Sleeps 10

Hamptons Hideaway

$579 avg / night (excludes fees and taxes)
Hampton Bays, NY
4.0 (2)
4 Bedrooms | 3.5 Bath | Sleeps 10

The Blissful Bay House

$1,242 avg / night (excludes fees and taxes)
Hampton Bays, NY
5.0 (4)
4 Bedrooms | 5 Bath | Sleeps 11

Tranquil Bays Estate

$637 avg / night (excludes fees and taxes)
NEW!
Hampton Bays, NY
4 Bedrooms | 4.5 Bath | Sleeps 10
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