Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Chestertown
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
New York
New York
Europe
Europe
Canada
Canada
Caribbean
Caribbean
Italy
Italy
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Countryside
Cabins
Lakefront
Amazing views
Amazing pools
Rooms
Ski-in/out
Play
Farms
Tiny homes
Chef's kitchens
Bed & breakfasts
Vineyards
New
Off-the-grid
Trending
Camping
A-frames
Design
Barns
Golfing
Grand pianos
Mansions
Skiing
Lake
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places in Chestertown
Over 1,000 places in Chestertown
Superhost
Superhost
Home in Chestertown
Secluded and Cozy Townhome near Tripp Lake
Apr 19 – 24
Apr 19 – 24
$225
$90
night
$90 per night, originally $225
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Chestertown
Adirondack Lake House
3 beds
3 beds
Apr 19 – 24
Apr 19 – 24
$200
night
$200 per night
4.95 out of 5 average rating, 206 reviews
4.95 (206)
Guest favorite
Guest favorite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
5 beds
5 beds
Apr 29 – May 4
Apr 29 – May 4
$290
night
$290 per night
4.96 out of 5 average rating, 67 reviews
4.96 (67)
Guest favorite
Guest favorite
Home in Chestertown
The Hayes Homestead
4 beds
4 beds
Apr 19 – 24
Apr 19 – 24
$200
night
$200 per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Chestertown
Chestertown Charm close to Gore Mt. Come ski!
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
$225
$147
night
$147 per night, originally $225
4.85 out of 5 average rating, 20 reviews
4.85 (20)
Home in Chestertown
Friends Lake Oasis
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$358
night
$358 per night
New place to stay
New
Guest favorite
Guest favorite
8
Reviews
5.0
Rating
1
Year hosting
Room in Warrensburg
Stay with Hanna
Stay with Hanna
Engineering tech
,
·
Engineering tech
ADK Serenity Farmhouse 1.0
Apr 22 – 27
Apr 22 – 27
$60
$54
night
$54 per night, originally $60
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Home in Chestertown
Stunning Lakefront House on Loon Lake!
7 beds
7 beds
May 3 – 10
May 3 – 10
$314
night
$314 per night
New place to stay
New
Home in Chestertown
Mimi’s by the lake
9 beds
9 beds
Apr 19 – 24
Apr 19 – 24
$563
$419
night
$419 per night, originally $563
4.88 out of 5 average rating, 8 reviews
4.88 (8)
Guest favorite
Guest favorite
Home in Chestertown
Cozy Adirondack Victorian! Ski, hike, swim, enjoy!
5 beds
5 beds
May 1 – 6
May 1 – 6
$325
night
$325 per night
4.96 out of 5 average rating, 47 reviews
4.96 (47)
Guest favorite
Guest favorite
Home in Chestertown
Eagles Nest @ Loon Lake near Gore Mountain
11 beds
11 beds
Apr 19 – 24
Apr 19 – 24
$453
night
$453 per night
4.98 out of 5 average rating, 104 reviews
4.98 (104)
Guest favorite
Guest favorite
Home in Chestertown
The Stone Lodge on Blythewood Island in Loon Lake
6 beds
6 beds
Apr 20 – 25
Apr 20 – 25
$350
night
$350 per night
4.93 out of 5 average rating, 141 reviews
4.93 (141)
Guest favorite
Guest favorite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
6 beds
6 beds
Apr 19 – 24
Apr 19 – 24
$238
$202
night
$202 per night, originally $238
4.96 out of 5 average rating, 80 reviews
4.96 (80)
Superhost
Superhost
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$245
night
$245 per night
4.9 out of 5 average rating, 31 reviews
4.9 (31)
Guest favorite
Guest favorite
Home in Chestertown
Spacious Chestertown Home ~ 22 Mi to Gore Mountain
6 beds
6 beds
Apr 26 – May 1
Apr 26 – May 1
$225
night
$225 per night
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
6 beds
6 beds
Apr 28 – May 3
Apr 28 – May 3
$164
night
$164 per night
4.85 out of 5 average rating, 33 reviews
4.85 (33)
3
Reviews
4.67
Rating
1
Year hosting
Room in Warrensburg
Stay with Hanna
Stay with Hanna
Engineering tech
,
·
Engineering tech
ADK Serenity Farmhouse 2.0
Apr 22 – 27
Apr 22 – 27
$55
night
$55 per night
4.67 out of 5 average rating, 3 reviews
4.67 (3)
Home in Chestertown
Beautiful 2BR Riverfront Adirondacks | Hot Tub
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
$162
night
$162 per night
4.33 out of 5 average rating, 6 reviews
4.33 (6)
1
2
3
4
…
15