The Best Airbnb Deals in
Chestertown, New York

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

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AirDNA Score: 73
$180/night

The Lily Pad at Loon Lake near Gore Mountain

4 beds
2 baths
11 guests
Average Price:  
$300
40% Cheaper
than normal
AirDNA Score: 73
$103/night

Lily Pad North at Loon Lake near Gore Mountain

2 beds
1 bath
6 guests
Average Price:  
$152
32% Cheaper
than normal
AirDNA Score: 68
$375/night

The Roost, a lake front 4 season home

4 beds
3 baths
9 guests
Average Price:  
$442
15% Cheaper
than normal
AirDNA Score: 66
$104/night

Lily Pad South at Loon Lake near Gore Mountain

2 beds
1 bath
5 guests
Average Price:  
$158
34% Cheaper
than normal
AirDNA Score: 65
$250/night

Rita''s Place

3 beds
2 baths
6 guests
Average Price:  
$324
23% Cheaper
than normal
AirDNA Score: 65
$300/night

High End Condo - Plenty of SNOW. Book your stay!

3 beds
2.5 baths
8 guests
Average Price:  
$353
15% Cheaper
than normal
AirDNA Score: 64
$202/night

Meadow House

5 beds
3 baths
10 guests
Average Price:  
$367
45% Cheaper
than normal
AirDNA Score: 64
$400/night

Lake George Adirondack stye house

5 beds
2 baths
12 guests
Average Price:  
$458
13% Cheaper
than normal
AirDNA Score: 59
$460/night

Large Apartment Rental in Chestertown

4 beds
4.5 baths
10 guests
Average Price:  
$548
16% Cheaper
than normal
AirDNA Score: 59
$363/night

The Cabin at Loch Loon

4 beds
2 baths
10 guests
Average Price:  
$397
9% Cheaper
than normal
AirDNA Score: 51
$346/night

Luxury in the Adirondacks - 16 ppl!

4 beds
4.5 baths
16 guests
Average Price:  
$370
6% Cheaper
than normal
AirDNA Score: 49
$325/night

Loon Lake Luxury with kayaks and canoe

3 beds
3 baths
8 guests
Average Price:  
$418
22% Cheaper
than normal
AirDNA Score: 43
$248/night

High Pines Hideaway Four Season Getaway

2 beds
2 baths
8 guests
Average Price:  
$301
18% Cheaper
than normal
AirDNA Score: 39
$350/night

The Stone Lodge on Blythewood Island in Loon Lake

4 beds
2.5 baths
10 guests
Average Price:  
$379
8% Cheaper
than normal
AirDNA Score: 34
$135/night

The Ramblewood. Family Friendly.

5 beds
3 baths
12 guests
Average Price:  
$216
37% Cheaper
than normal
AirDNA Score: 31
$211/night

Spacious 4BR Friends Lake, NY | Dock | Firepit

4 beds
2 baths
6 guests
Average Price:  
$292
28% Cheaper
than normal
AirDNA Score: 29
$438/night

Beautiful 5BR Lakefront Adirondacks | Dock

5 beds
3 baths
10 guests
Average Price:  
$487
10% Cheaper
than normal
AirDNA Score: 21
$220/night

Friends Lake Retreat

2 beds
1 bath
6 guests
Average Price:  
$220
0% Cheaper
than normal
AirDNA Score: 21
$735/night

Historic 6BR Mountainview Adirondacks

6 beds
5 baths
11 guests
Average Price:  
$841
13% Cheaper
than normal
AirDNA Score: 11
$338/night

Loon Lake fun, HOT TUB. Close to Gore&Lake George

3 beds
3 baths
8 guests
Average Price:  
$399
15% Cheaper
than normal