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
$650/night

Hay Beach Oasis

3 beds
2 baths
6 guests
Average Price:  
$759
14% Cheaper
than normal
AirDNA Score: 73
$800/night

Shelter Island Cottage

5 beds
1.5 baths
8 guests
Average Price:  
$853
6% Cheaper
than normal
AirDNA Score: 72
$400/night

Summer Paradise 4BR on Shelter Island

4 beds
2 baths
8 guests
Average Price:  
$405
1% Cheaper
than normal
AirDNA Score: 71
$300/night

Secluded Shelter Island cottage

3 beds
1.5 baths
5 guests
Average Price:  
$395
24% Cheaper
than normal
AirDNA Score: 71
$375/night

Waterfront carriage house studio

1 bed
1 bath
4 guests
Average Price:  
$350
7% More
than normal
AirDNA Score: 69
$695/night

Midcentury Style

2 beds
2 baths
4 guests
Average Price:  
$699
1% Cheaper
than normal
AirDNA Score: 66
$1500/night

Ideal for Families!

5 beds
3.5 baths
10 guests
Average Price:  
$1538
2% Cheaper
than normal
AirDNA Score: 65
$5000/night

Stunning Shelter Island House with pool and beach

5 beds
4.5 baths
10 guests
Average Price:  
$3346
49% More
than normal
AirDNA Score: 64
$950/night

Stunning water views, huge pool, family resort

4 beds
3 baths
7 guests
Average Price:  
$1177
19% Cheaper
than normal
AirDNA Score: 64
$900/night

Modern, spacious SI home with pool

4 beds
3 baths
8 guests
Average Price:  
$844
7% More
than normal
AirDNA Score: 61
$550/night

SHELTER ISLAND House w Pool peaceful 2+ acres

3 beds
2 baths
6 guests
Average Price:  
$691
20% Cheaper
than normal
AirDNA Score: 60
$305/night

Waterfront Cottage on Private Estate

1 bed
1 bath
4 guests
Average Price:  
$346
12% Cheaper
than normal
AirDNA Score: 57
$996/night

Shelter Island Manor

5 beds
6 baths
10 guests
Average Price:  
$1197
17% Cheaper
than normal
AirDNA Score: 57
$299/night

Charming & Elegant Shelter Island Suite

1 bed
1 bath
2 guests
Average Price:  
$350
15% Cheaper
than normal
AirDNA Score: 53
$488/night

Picturesque waterfront cottage

2 beds
1.5 baths
5 guests
Average Price:  
$504
3% Cheaper
than normal
AirDNA Score: 52
$6000/night

Fab Shelter Island Listing, 2 acr Property w/Pool

6 beds
3.5 baths
12 guests
Average Price:  
$5378
12% More
than normal
AirDNA Score: 52
$559/night

Waterfront Estate on Shelter Island. 100 Ft Dock

4 beds
3 baths
8 guests
Average Price:  
$1167
52% Cheaper
than normal
AirDNA Score: 52
$1630/night

Huge Island Getaway Pool HotTub By Beach

5 beds
5.5 baths
11 guests
Average Price:  
$1295
26% More
than normal
AirDNA Score: 51
$950/night

SLEEK, RENOVATED SHELTER ISLAND GEM

3 beds
3 baths
8 guests
Average Price:  
$1088
13% Cheaper
than normal
AirDNA Score: 51
$950/night

Shelter Island Hidden Waterfront

3 beds
2.5 baths
8 guests
Average Price:  
$1070
11% Cheaper
than normal
AirDNA Score: 51
$750/night

Shelter Island''s Silver Beach Home

3 beds
2.5 baths
8 guests
Average Price:  
$617
22% More
than normal
AirDNA Score: 50
$1200/night

Shelter Island Waterfront, Pool and Dock

4 beds
2.5 baths
8 guests
Average Price:  
$861
39% More
than normal
AirDNA Score: 50
$1150/night

Designer Renovated Farmhouse with Pool

3 beds
2 baths
6 guests
Average Price:  
$1299
11% Cheaper
than normal
AirDNA Score: 37
$1000/night

West Neck Landing - Waterfront on Shelter Island

2 beds
2 baths
4 guests
Average Price:  
$971
3% More
than normal
AirDNA Score: 36
$335/night

Large Waterfront Cottage on Historic Estate

3 beds
1 bath
6 guests
Average Price:  
$450
26% Cheaper
than normal
AirDNA Score: 33
$750/night

Charming Coastal Cottage

3 beds
1.5 baths
6 guests
Average Price:  
$896
16% Cheaper
than normal
AirDNA Score: 31
$500/night

Shelter Island Getaway

3 beds
2.5 baths
8 guests
Average Price:  
$746
33% Cheaper
than normal
AirDNA Score: 23
$600/night

SI house with pool new grill and new patio set

4 beds
2 baths
6 guests
Average Price:  
$456
32% More
than normal
AirDNA Score: 15
$620/night

Refined, Pristine Farmhouse, Shelter Island, NY

3 beds
2 baths
4 guests
Average Price:  
$719
14% Cheaper
than normal