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: 68
$275/night

Comfortable Cottage on the Great Pond near beach.

2 beds
1.5 baths
4 guests
Average Price:  
$257
7% More
than normal
AirDNA Score: 64
$1500/night

Nautical North Fork Bayfront Home - Walk to Town!

4 beds
5.5 baths
8 guests
Average Price:  
$1192
26% More
than normal
AirDNA Score: 59
$428/night

Southold Beach house.

4 beds
3 baths
8 guests
Average Price:  
$607
29% Cheaper
than normal
AirDNA Score: 58
$399/night

NoFo 3 BR + Den | Waterfront | Dock | Sleeps 8

3 beds
3 baths
8 guests
Average Price:  
$592
33% Cheaper
than normal
AirDNA Score: 57
$600/night

Mediterranean style home

3 beds
1.5 baths
6 guests
Average Price:  
$444
35% More
than normal
AirDNA Score: 54
$1250/night

North Fork Villa Unique gem!Pool, beach, vineyards

6 beds
4 baths
14 guests
Average Price:  
$1636
24% Cheaper
than normal
AirDNA Score: 52
$584/night

Beach house @ NoFo

3 beds
2 baths
10 guests
Average Price:  
$659
11% Cheaper
than normal
AirDNA Score: 52
$655/night

Renovated Farmhouse w/ Pool & Outdoor Fireplace

4 beds
3 baths
7 guests
Average Price:  
$1101
41% Cheaper
than normal
AirDNA Score: 51
$395/night

Spectacular waterfront, sunset views, immaculate

3 beds
2 baths
7 guests
Average Price:  
$590
33% Cheaper
than normal
AirDNA Score: 51
$1200/night

North Fork Family Getaway

4 beds
3.5 baths
8 guests
Average Price:  
$1276
6% Cheaper
than normal
AirDNA Score: 50
$773/night

Brand New Modern Farmhouse Estate with heated pool

8 beds
7 baths
12 guests
Average Price:  
$1192
35% Cheaper
than normal
AirDNA Score: 50
$699/night

Shorecrest Beach House, N Fork, LI

4 beds
2 baths
10 guests
Average Price:  
$859
19% Cheaper
than normal
AirDNA Score: 50
$650/night

Luxury Southold waterfront home, heated pool & spa

4 beds
4 baths
8 guests
Average Price:  
$1008
36% Cheaper
than normal
AirDNA Score: 47
$425/night

SOUTHOLD KENNEY''S BEACH 4 BEDRMS

4 beds
2.5 baths
8 guests
Average Price:  
$246
73% More
than normal
AirDNA Score: 46
$190/night

Casa Good Times

6 beds
4 baths
10 guests
Average Price:  
$441
57% Cheaper
than normal
AirDNA Score: 45
$900/night

North Fork Hideaway

4 beds
3 baths
8 guests
Average Price:  
$1358
34% Cheaper
than normal
AirDNA Score: 45
$490/night

Perfect stay near wineries & beaches in Southold

3 beds
1.5 baths
6 guests
Average Price:  
$603
19% Cheaper
than normal
AirDNA Score: 44
$1050/night

Sandy beachfront home in Southold

3 beds
2.5 baths
8 guests
Average Price:  
$1325
21% Cheaper
than normal
AirDNA Score: 42
$300/night

STATELY, PRISTINE, PEACEFUL WITH FIREPLACES

4 beds
4 baths
6 guests
Average Price:  
$975
69% Cheaper
than normal
AirDNA Score: 41
$250/night

Cozy&Chic Beach Cottage (Great 4 remote work too)

2 beds
1.5 baths
4 guests
Average Price:  
$354
29% Cheaper
than normal
AirDNA Score: 40
$750/night

Charming North Fork Getaway with pool!

4 beds
2 baths
8 guests
Average Price:  
$833
10% Cheaper
than normal
AirDNA Score: 37
$550/night

NoFo Retreat w/ Private Basketball Court & Hot Tub

4 beds
2 baths
8 guests
Average Price:  
$562
2% Cheaper
than normal
AirDNA Score: 37
$1250/night

Southold waterfront 4 bed, pool open til October

4 beds
3 baths
10 guests
Average Price:  
$1266
1% Cheaper
than normal
AirDNA Score: 35
$600/night

Beachwood Cottage JUST RENOVATED!

3 beds
2 baths
6 guests
Average Price:  
$635
6% Cheaper
than normal
AirDNA Score: 30
$325/night

Southold Bay Beach House

4 beds
2 baths
8 guests
Average Price:  
$732
56% Cheaper
than normal
AirDNA Score: 29
$275/night

Cottage in Founders Landing, Southold

2 beds
1 bath
4 guests
Average Price:  
$281
2% Cheaper
than normal
AirDNA Score: 29
$315/night

WATERFRONT Southold Retreat! Steps to Beaches!

4 beds
4 baths
10 guests
Average Price:  
$594
47% Cheaper
than normal
AirDNA Score: 29
$252/night

Lovely North Fork (LI) home, 5 min walk to beach.

3 beds
2 baths
6 guests
Average Price:  
$264
5% Cheaper
than normal
AirDNA Score: 28
$248/night

Modern & Spacious Beachfront Living

2 beds
3 baths
4 guests
Average Price:  
$368
33% Cheaper
than normal
AirDNA Score: 23
$1000/night

Magical modern waterfront home

4 beds
3.5 baths
8 guests
Average Price:  
$1041
4% Cheaper
than normal
AirDNA Score: 23
$125/night

Southold Beach Cottage Fall Winter Summer Yearly

2 beds
1 bath
2 guests
Average Price:  
$186
33% Cheaper
than normal
AirDNA Score: 21
$340/night

North Fork Beach House

3 beds
2 baths
6 guests
Average Price:  
$416
18% Cheaper
than normal
AirDNA Score: 19
$1300/night

Perfect North Fork Getaway for Family & Friends

4 beds
2.5 baths
12 guests
Average Price:  
$1344
3% Cheaper
than normal
AirDNA Score: 15
$700/night

Paradise 4 Shore

4 beds
3 baths
12 guests
Average Price:  
$817
14% Cheaper
than normal
AirDNA Score: 14
$1000/night

LUXURY NORTH FORK WITH POOL

4 beds
3.5 baths
8 guests
Average Price:  
$1311
24% Cheaper
than normal