The Best Airbnb Deals in
Southold, New York

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Southold, New York. Enter your travel dates to find the best deals!

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AirDNA Score: 62
$399/night

Cozy Barn Loft Apartment on the NOFO Wine Trail

studio
1 bath
2 guests
Average Price:  
$425
6% Cheaper
than normal
AirDNA Score: 58
$375/night

Captain''s Cove

2 beds
1 bath
4 guests
Average Price:  
$395
5% Cheaper
than normal
AirDNA Score: 54
$1499/night

North Fork Villa Unique gem!Pool, beach, vineyards

6 beds
4 baths
14 guests
Average Price:  
$1702
12% Cheaper
than normal
AirDNA Score: 51
$547/night

Spectacular waterfront, sunset views, immaculate

3 beds
2 baths
7 guests
Average Price:  
$637
14% Cheaper
than normal
AirDNA Score: 51
$800/night

Waterfront Home for Rent

4 beds
3.5 baths
8 guests
Average Price:  
$894
11% Cheaper
than normal
AirDNA Score: 50
$1175/night

Spectacular 5 Bedroom Home in the North Fork

5 beds
4 baths
10 guests
Average Price:  
$1091
8% More
than normal
AirDNA Score: 50
$1750/night

Luxury Southold waterfront home, heated pool & spa

4 beds
4 baths
8 guests
Average Price:  
$1454
20% More
than normal
AirDNA Score: 50
$804/night

Shorecrest Beach House, N Fork, LI

4 beds
2 baths
10 guests
Average Price:  
$758
6% More
than normal
AirDNA Score: 47
$385/night

SOUTHOLD KENNEY''S BEACH 4 BEDRMS

4 beds
2.5 baths
8 guests
Average Price:  
$592
35% Cheaper
than normal
AirDNA Score: 46
$648/night

Casa Good Times

6 beds
4 baths
10 guests
Average Price:  
$458
41% More
than normal
AirDNA Score: 45
$1000/night

North Fork Hideaway

4 beds
3 baths
8 guests
Average Price:  
$1484
33% Cheaper
than normal
AirDNA Score: 44
$900/night

Sandy beachfront home in Southold

3 beds
2.5 baths
8 guests
Average Price:  
$960
6% Cheaper
than normal
AirDNA Score: 41
$205/night

Southold Cottage on Beach-Great 4 remote work too!

2 beds
1.5 baths
4 guests
Average Price:  
$355
42% Cheaper
than normal
AirDNA Score: 37
$1000/night

Southold waterfront 4 bed, pool open til October

4 beds
3 baths
10 guests
Average Price:  
$1318
24% Cheaper
than normal
AirDNA Score: 35
$650/night

Beachwood Cottage JUST RENOVATED!

3 beds
2 baths
6 guests
Average Price:  
$786
17% Cheaper
than normal
AirDNA Score: 29
$420/night

WATERFRONT Southold Retreat! Steps to Beaches!

4 beds
4 baths
16 guests
Average Price:  
$581
28% Cheaper
than normal
AirDNA Score: 24
$275/night

Southold Lakefront with Hot Tub & view of LI Sound

4 beds
2 baths
8 guests
Average Price:  
$372
26% Cheaper
than normal
AirDNA Score: 23
$225/night

Sweet Southold Beach Cottage SPRING/SUMMER/YEARLY

2 beds
1 bath
2 guests
Average Price:  
$218
3% More
than normal
AirDNA Score: 23
$925/night

Magical modern waterfront home

4 beds
3.5 baths
8 guests
Average Price:  
$1011
9% Cheaper
than normal
AirDNA Score: 15
$700/night

Paradise 4 Shore

4 beds
3 baths
12 guests
Average Price:  
$730
4% Cheaper
than normal
AirDNA Score: 14
$299/night

Beautiful BEACHFRONT Family Home with huge yard!!

3 beds
2 baths
8 guests
Average Price:  
$485
38% Cheaper
than normal
AirDNA Score: 14
$800/night

North Fork Long Island Beach Front 5 bedroom

5 beds
3.5 baths
12 guests
Average Price:  
$671
19% More
than normal
AirDNA Score: 0
$485/night

Private Beachfront Getaway

2 beds
1 bath
4 guests
Average Price:  
$515
6% Cheaper
than normal