The Best Airbnb Deals in
Shelter Island, New York

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

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AirDNA Score: 73
$517/night

Hay Beach Getaway!

3 beds
2 baths
6 guests
Average Price:  
$701
26% Cheaper
than normal
AirDNA Score: 73
$1050/night

Shelter Island Cottage

5 beds
1.5 baths
8 guests
Average Price:  
$1022
3% More
than normal
AirDNA Score: 72
$300/night

Charming 4BR Cottage on Shelter Island

4 beds
2 baths
8 guests
Average Price:  
$400
25% Cheaper
than normal
AirDNA Score: 71
$475/night

3 Bedroom Cottage Gem

3 beds
2.5 baths
6 guests
Average Price:  
$615
23% Cheaper
than normal
AirDNA Score: 71
$250/night

Secluded Shelter Island cottage

3 beds
1.5 baths
5 guests
Average Price:  
$380
34% Cheaper
than normal
AirDNA Score: 67
$895/night

Chic Shelter Island Home, Gunite Pool

3 beds
2 baths
6 guests
Average Price:  
$1346
34% Cheaper
than normal
AirDNA Score: 64
$1625/night

Stunning water views, huge pool, family resort

4 beds
3 baths
7 guests
Average Price:  
$1357
20% More
than normal
AirDNA Score: 64
$813/night

Modern, spacious SI home with pool

4 beds
3 baths
8 guests
Average Price:  
$919
12% Cheaper
than normal
AirDNA Score: 61
$450/night

SHELTER ISLAND House w Pool peaceful 2+ acres

3 beds
2 baths
6 guests
Average Price:  
$616
27% Cheaper
than normal
AirDNA Score: 57
$596/night

Beautiful beach home with pool & water views!

5 beds
3.5 baths
8 guests
Average Price:  
$972
39% Cheaper
than normal
AirDNA Score: 55
$733/night

Chic, serene, designer home with pool and views

3 beds
3 baths
6 guests
Average Price:  
$1169
37% Cheaper
than normal
AirDNA Score: 55
$375/night

Tasteful, Relaxing Getaway

3 beds
2 baths
6 guests
Average Price:  
$375
0% Cheaper
than normal
AirDNA Score: 53
$475/night

Picturesque waterfront cottage

2 beds
1.5 baths
5 guests
Average Price:  
$518
8% Cheaper
than normal
AirDNA Score: 52
$4498/night

Fab Shelter Island Listing, 2 acr Property w/Pool

6 beds
3.5 baths
12 guests
Average Price:  
$5851
23% Cheaper
than normal
AirDNA Score: 52
$500/night

Waterfront Haven

5 beds
4.5 baths
8 guests
Average Price:  
$968
48% Cheaper
than normal
AirDNA Score: 52
$879/night

Waterfront Estate on Shelter Island. 100 Ft Dock

4 beds
3 baths
8 guests
Average Price:  
$995
12% Cheaper
than normal
AirDNA Score: 51
$600/night

Directly on best beach, with water/sunset views

3 beds
2 baths
6 guests
Average Price:  
$810
26% Cheaper
than normal
AirDNA Score: 51
$500/night

SLEEK, RENOVATED SHELTER ISLAND GEM

3 beds
3 baths
8 guests
Average Price:  
$1080
54% Cheaper
than normal
AirDNA Score: 51
$650/night

Shelter Island''s Silver Beach Home

3 beds
2.5 baths
8 guests
Average Price:  
$736
12% Cheaper
than normal
AirDNA Score: 50
$650/night

Shelter Island Waterfront, Pool and Dock

4 beds
2.5 baths
8 guests
Average Price:  
$861
25% Cheaper
than normal
AirDNA Score: 37
$700/night

Serenity on Shelter Island with a Pool & Hot tub

3 beds
2 baths
6 guests
Average Price:  
$812
14% Cheaper
than normal
AirDNA Score: 37
$720/night

West Neck Landing - Waterfront on Shelter Island

2 beds
2 baths
4 guests
Average Price:  
$941
23% Cheaper
than normal
AirDNA Score: 36
$752/night

The Lord‘s Villa & Estate

4 beds
3 baths
8 guests
Average Price:  
$2177
65% Cheaper
than normal
AirDNA Score: 34
$600/night

Shelter Island home with pool

4 beds
2.5 baths
8 guests
Average Price:  
$918
35% Cheaper
than normal
AirDNA Score: 31
$800/night

Shelter Island Getaway

3 beds
2.5 baths
8 guests
Average Price:  
$700
14% More
than normal
AirDNA Score: 29
$500/night

Shelter Island Sundrenched Retreat /walk to beach

3 beds
2 baths
6 guests
Average Price:  
$558
10% Cheaper
than normal
AirDNA Score: 23
$218/night

Shelter Island Cottage with AirCon, Pool, Peloton

4 beds
2 baths
6 guests
Average Price:  
$568
62% Cheaper
than normal