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:  
$277
1% Cheaper
than normal
AirDNA Score: 58
$500/night

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

3 beds
3 baths
8 guests
Average Price:  
$701
29% 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
$1916/night

North Fork Villa Unique gem!Pool, beach, vineyards

6 beds
4 baths
14 guests
Average Price:  
$1587
21% More
than normal
AirDNA Score: 52
$987/night

Beach house @ NoFo

3 beds
2 baths
10 guests
Average Price:  
$657
50% More
than normal
AirDNA Score: 52
$1280/night

Renovated Farmhouse w/ Pool & Outdoor Fireplace

4 beds
3 baths
7 guests
Average Price:  
$1136
13% More
than normal
AirDNA Score: 50
$874/night

Luxury Southold waterfront home, heated pool & spa

4 beds
4 baths
8 guests
Average Price:  
$1115
22% Cheaper
than normal
AirDNA Score: 50
$693/night

Waterfront with Private Beaches and Sunset Views

3 beds
2.5 baths
6 guests
Average Price:  
$682
2% More
than normal
AirDNA Score: 48
$396/night

The Perfect North Fork Pied-A-Terre Permit #0170

1 bed
1 bath
2 guests
Average Price:  
$383
3% More
than normal
AirDNA Score: 47
$425/night

SOUTHOLD KENNEY'S BEACH 4 BEDRMS

4 beds
2.5 baths
8 guests
Average Price:  
$275
55% More
than normal
AirDNA Score: 46
$456/night

Casa Good Times

6 beds
4 baths
10 guests
Average Price:  
$427
7% More
than normal
AirDNA Score: 45
$900/night

North Fork Hideaway

4 beds
3 baths
8 guests
Average Price:  
$1349
33% Cheaper
than normal
AirDNA Score: 44
$1413/night

Sandy beachfront home in Southold

3 beds
2.5 baths
8 guests
Average Price:  
$1350
5% More
than normal
AirDNA Score: 40
$800/night

Charming North Fork Getaway with pool!

4 beds
2 baths
8 guests
Average Price:  
$858
7% Cheaper
than normal
AirDNA Score: 37
$750/night

Southold waterfront 4 bed, pool open til October

4 beds
3 baths
10 guests
Average Price:  
$1249
40% 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: 29
$1100/night

WATERFRONT Southold Retreat! Steps to Beaches!

4 beds
4 baths
10 guests
Average Price:  
$594
85% More
than normal
AirDNA Score: 28
$243/night

Modern & Spacious Beachfront Living

2 beds
3 baths
4 guests
Average Price:  
$368
34% Cheaper
than normal
AirDNA Score: 23
$1030/night

Magical modern waterfront home

4 beds
3.5 baths
8 guests
Average Price:  
$1063
3% Cheaper
than normal
AirDNA Score: 22
$688/night

Eat, Love, Stay, and Wellness

3 beds
1.5 baths
6 guests
Average Price:  
$752
9% 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:  
$820
15% Cheaper
than normal
AirDNA Score: 14
$1329/night

LUXURY NORTH FORK WITH POOL

4 beds
3.5 baths
8 guests
Average Price:  
$1311
1% More
than normal