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: 79
$200/night

Adirondack Lake House

2 beds
1 bath
5 guests
Average Price:  
$200
0% Cheaper
than normal
AirDNA Score: 75
$99/night

1920s Honeymoon Cottage ADK Enchanted Nites Airbnb

studio
1 bath
2 guests
Average Price:  
$123
20% 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:  
$184
44% Cheaper
than normal
AirDNA Score: 73
$196/night

The Lily Pad at Loon Lake near Gore Mountain

4 beds
2 baths
11 guests
Average Price:  
$315
38% Cheaper
than normal
AirDNA Score: 69
$335/night

Eagles Nest @ Loon Lake near Gore Mountain

7 beds
4 baths
16 guests
Average Price:  
$510
34% Cheaper
than normal
AirDNA Score: 68
$375/night

The Roost, a lake front 4 season home

4 beds
3 baths
9 guests
Average Price:  
$430
13% Cheaper
than normal
AirDNA Score: 66
$93/night

Lily Pad South at Loon Lake near Gore Mountain

2 beds
1 bath
5 guests
Average Price:  
$217
57% Cheaper
than normal
AirDNA Score: 64
$275/night

Meadow House

5 beds
3 baths
10 guests
Average Price:  
$317
13% Cheaper
than normal
AirDNA Score: 61
$325/night

Adirondack Lakefront Cabin - close to Gore skiing

3 beds
2.5 baths
6 guests
Average Price:  
$325
0% Cheaper
than normal
AirDNA Score: 60
$240/night

ADK MT/Lake 3 BDRM HSE for up to 3 Adults

3 beds
2.5 baths
5 guests
Average Price:  
$297
19% Cheaper
than normal
AirDNA Score: 59
$400/night

Large Apartment Rental in Chestertown

4 beds
4.5 baths
10 guests
Average Price:  
$800
50% Cheaper
than normal
AirDNA Score: 59
$325/night

The Cabin at Loch Loon

4 beds
2 baths
10 guests
Average Price:  
$310
5% More
than normal
AirDNA Score: 57
$174/night

Lakefront cabin with beautiful views, lake and beach access

1 bed
1.5 baths
2 guests
Average Price:  
$246
29% Cheaper
than normal
AirDNA Score: 57
$266/night

Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space

3 beds
1.5 baths
6 guests
Average Price:  
$345
23% Cheaper
than normal
AirDNA Score: 57
$480/night

Two lakefront cabins with gorgeous views on two acres of land - dock & beach

4 beds
3.5 baths
8 guests
Average Price:  
$734
35% Cheaper
than normal
AirDNA Score: 55
$445/night

Adirondack Private Lakefront Knotty Pine Cabin

3 beds
2 baths
8 guests
Average Price:  
$468
5% Cheaper
than normal
AirDNA Score: 54
$299/night

Gore Mt. Ski House/Adirondack 4 Season Retreat

3 beds
2.5 baths
10 guests
Average Price:  
$299
0% Cheaper
than normal
AirDNA Score: 51
$285/night

Luxury in the Adirondacks - 16 ppl!

4 beds
4.5 baths
16 guests
Average Price:  
$354
19% Cheaper
than normal
AirDNA Score: 49
$375/night

Loon Lake Luxury with kayaks and canoe

3 beds
3 baths
8 guests
Average Price:  
$395
5% Cheaper
than normal
AirDNA Score: 43
$250/night

High Pines Hideaway Four Season Getaway

2 beds
2 baths
8 guests
Average Price:  
$276
9% Cheaper
than normal
AirDNA Score: 41
$219/night

Adirondack Camp / Friends Lake

4 beds
1 bath
7 guests
Average Price:  
$229
4% Cheaper
than normal
AirDNA Score: 37
$239/night

Fish, Swim, Peep, Ski! - Loon Lake Creek Side

3 beds
1.5 baths
6 guests
Average Price:  
$298
20% Cheaper
than normal
AirDNA Score: 35
$499/night

Elizabeth. A Guest House Near Lake George.

6 beds
3 baths
16 guests
Average Price:  
$806
38% Cheaper
than normal
AirDNA Score: 34
$175/night

The Ramblewood. Family Friendly.

6 beds
3 baths
12 guests
Average Price:  
$262
33% Cheaper
than normal
AirDNA Score: 31
$257/night

Big single-level house with firepit & spacious yard - lake access nearby

4 beds
2 baths
6 guests
Average Price:  
$291
12% Cheaper
than normal
AirDNA Score: 29
$422/night

Lakefront cabin with beautiful loft, game room, views, private dock

5 beds
3 baths
10 guests
Average Price:  
$552
24% Cheaper
than normal
AirDNA Score: 29
$212/night

Lakefront cottage w/ full kitchen, sandy beach, dock and swim float

3 beds
2 baths
6 guests
Average Price:  
$326
35% Cheaper
than normal
AirDNA Score: 23
$297/night

Dog-friendly, lakefront camp cabin w/ a dock & multiple decks

3 beds
2 baths
6 guests
Average Price:  
$353
16% Cheaper
than normal
AirDNA Score: 23
$264/night

Dog-friendly cabin with lakefront location, 20'' dock, smart TV

3 beds
1 bath
8 guests
Average Price:  
$327
19% Cheaper
than normal
AirDNA Score: 22
$404/night

Dog-friendly lakefront house with 2 living areas, beach nearby

4 beds
3 baths
8 guests
Average Price:  
$518
22% Cheaper
than normal
AirDNA Score: 22
$426/night

Lakefront, two-story Adirondack log cabin with dock and sandy beach

4 beds
2 baths
8 guests
Average Price:  
$556
23% Cheaper
than normal
AirDNA Score: 21
$192/night

Cozy cottage with deeded lake rights - 100 steps to the beach

4 beds
1.5 baths
8 guests
Average Price:  
$268
28% Cheaper
than normal
AirDNA Score: 21
$724/night

Historic Greek Revival style home w/ screened in porch -near attractions!

6 beds
5 baths
11 guests
Average Price:  
$1013
29% Cheaper
than normal
AirDNA Score: 15
$429/night

ADK Farmhouse, 10 Minutes from Gore Mountain

4 beds
2 baths
10 guests
Average Price:  
$463
7% Cheaper
than normal
AirDNA Score: 11
$375/night

Loon Lake fun with kayaks, HOT TUB. Close to Gore.

3 beds
3 baths
8 guests
Average Price:  
$425
12% Cheaper
than normal