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
$500/night

Shelter Island get away

3 beds
2 baths
6 guests
Average Price:  
$653
23% Cheaper
than normal
AirDNA Score: 73
$848/night

Shelter Island Cottage

5 beds
1.5 baths
8 guests
Average Price:  
$896
5% Cheaper
than normal
AirDNA Score: 71
$325/night

Secluded Shelter Island cottage

3 beds
1.5 baths
5 guests
Average Price:  
$366
11% Cheaper
than normal
AirDNA Score: 67
$2500/night

High End Shelter Island Complex with Outstanding Pool

8 beds
6.5 baths
14 guests
Average Price:  
$2553
2% Cheaper
than normal
AirDNA Score: 65
$155/night

Studio sweet on Shelter Island

1 bed
1 bath
2 guests
Average Price:  
$175
11% Cheaper
than normal
AirDNA Score: 65
$2500/night

Stunning Shelter Island House with pool and beach

5 beds
4.5 baths
10 guests
Average Price:  
$2203
13% More
than normal
AirDNA Score: 64
$1000/night

Stunning water views, pool, family retreat

4 beds
3 baths
7 guests
Average Price:  
$1268
21% Cheaper
than normal
AirDNA Score: 64
$650/night

Modern, spacious SI home with pool

4 beds
3 baths
8 guests
Average Price:  
$670
3% Cheaper
than normal
AirDNA Score: 59
$2000/night

Hay Beach Newly Renovated Modern Home, Heated Pool

4 beds
3 baths
10 guests
Average Price:  
$1672
20% More
than normal
AirDNA Score: 57
$910/night

LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY MANICURED GARDENS & HEATED POOL (AS SEEN IN WSJ)

5 beds
6 baths
10 guests
Average Price:  
$1031
12% Cheaper
than normal
AirDNA Score: 57
$299/night

Charming & Elegant Shelter Island Suite

1 bed
1 bath
2 guests
Average Price:  
$337
11% Cheaper
than normal
AirDNA Score: 57
$625/night

Beautiful spacious home -heated pool & water views

5 beds
3.5 baths
6 guests
Average Price:  
$839
26% Cheaper
than normal
AirDNA Score: 55
$549/night

Fully renovated, mid century modern luxe home

4 beds
3 baths
8 guests
Average Price:  
$946
42% Cheaper
than normal
AirDNA Score: 51
$1500/night

Island oasis with heated pool

3 beds
2 baths
6 guests
Average Price:  
$1590
6% Cheaper
than normal
AirDNA Score: 51
$500/night

Shelter Island Lake House Retreat

3 beds
2 baths
6 guests
Average Price:  
$520
4% Cheaper
than normal
AirDNA Score: 51
$1050/night

Shelter Island Hidden Waterfront

3 beds
2.5 baths
8 guests
Average Price:  
$1238
15% Cheaper
than normal
AirDNA Score: 51
$1050/night

SLEEK, RENOVATED SHELTER ISLAND GEM

3 beds
3 baths
8 guests
Average Price:  
$1144
8% Cheaper
than normal
AirDNA Score: 51
$800/night

Directly on best beach, with water/sunset views

3 beds
2 baths
6 guests
Average Price:  
$919
13% Cheaper
than normal
AirDNA Score: 51
$500/night

Shelter Island''s Silver Beach Home

3 beds
2.5 baths
8 guests
Average Price:  
$541
8% Cheaper
than normal
AirDNA Score: 50
$1000/night

Shelter Island Waterfront, Pool and Dock

4 beds
2.5 baths
8 guests
Average Price:  
$1008
1% Cheaper
than normal
AirDNA Score: 50
$1150/night

Designer Renovated Farmhouse with Pool

3 beds
2 baths
6 guests
Average Price:  
$1400
18% Cheaper
than normal
AirDNA Score: 41
$1000/night

Shelter Island Waterfront Home w/Cottage/Dock&Pool

4 beds
3 baths
8 guests
Average Price:  
$1053
5% Cheaper
than normal
AirDNA Score: 36
$450/night

Shelter Island 70s contemporary

3 beds
2 baths
6 guests
Average Price:  
$462
3% Cheaper
than normal
AirDNA Score: 36
$1199/night

The Lord‘s Villa & Estate

4 beds
3 baths
8 guests
Average Price:  
$1873
36% Cheaper
than normal
AirDNA Score: 35
$350/night

Shelter Island Getaway with Pool

3 beds
2 baths
6 guests
Average Price:  
$435
20% Cheaper
than normal
AirDNA Score: 34
$900/night

Shelter Island home with pool

4 beds
2.5 baths
8 guests
Average Price:  
$805
12% More
than normal
AirDNA Score: 33
$750/night

Charming Coastal Cottage

3 beds
1.5 baths
6 guests
Average Price:  
$747
0% Cheaper
than normal
AirDNA Score: 21
$260/night

Cozy, Comfortable Island Cottage

2 beds
1 bath
4 guests
Average Price:  
$334
22% Cheaper
than normal
AirDNA Score: 21
$600/night

Refined Cottage on Idyllic Shelter Island

3 beds
2 baths
6 guests
Average Price:  
$631
5% Cheaper
than normal
AirDNA Score: 15
$500/night

Family Fun Shelter Island House near Sunset Beach

4 beds
3 baths
6 guests
Average Price:  
$569
12% Cheaper
than normal