Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Chestertown
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Chestertown
Over 1,000 homes in Chestertown
Guest favourite
Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms
,
·
6 beds
,
·
2 private bathrooms
5–10 Jul
5–10 Jul
$2,175 SGD
Show price breakdown
for 5 nights
$2,175 SGD for 5 nights
,
·
4.92 out of 5 average rating, 120 reviews
4.92 (120)
Top guest favourite
Guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,526 SGD
Show price breakdown
for 5 nights
$1,526 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 259 reviews
4.95 (259)
Top guest favourite
Guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,302 SGD
$1,731 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 266 reviews
4.96 (266)
Guest favourite
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
2 bathrooms
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,901 SGD
Show price breakdown
for 5 nights
$2,901 SGD for 5 nights
4.89 out of 5 average rating, 38 reviews
4.89 (38)
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
5–10 Jul
5–10 Jul
$2,675 SGD
Show price breakdown
for 5 nights
$2,675 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$2,608 SGD
$2,180 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
9–14 Aug
9–14 Aug
$2,556 SGD
Show price breakdown
for 5 nights
$2,556 SGD for 5 nights
4.97 out of 5 average rating, 66 reviews
4.97 (66)
Guest favourite
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms
2 bedrooms
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$1,412 SGD
$1,282 SGD
Show price breakdown
for 5 nights
Extended stay discount
4.95 out of 5 average rating, 42 reviews
4.95 (42)
Top guest favourite
Guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,031 SGD
Show price breakdown
for 5 nights
$1,031 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 119 reviews
5.0 (119)
Guest favourite
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,702 SGD
Show price breakdown
for 5 nights
$1,702 SGD for 5 nights
4.92 out of 5 average rating, 53 reviews
4.92 (53)
Guest favourite
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms
2 bedrooms
,
·
7 beds
7 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,649 SGD
Show price breakdown
for 5 nights
$1,649 SGD for 5 nights
4.95 out of 5 average rating, 103 reviews
4.95 (103)
Home in Chestertown
Rustic Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Aug
9–14 Aug
$2,137 SGD
Show price breakdown
for 5 nights
$2,137 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Jul
25–30 Jul
$1,900 SGD
Show price breakdown
for 5 nights
$1,900 SGD for 5 nights
5.0 out of 5 average rating, 55 reviews
5.0 (55)
Cabin in Chestertown
Meadow House
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3 bathrooms
3 bathrooms
11–16 Jul
11–16 Jul
$2,492 SGD
Show price breakdown
for 5 nights
$2,492 SGD for 5 nights
4.88 out of 5 average rating, 161 reviews
4.88 (161)
Superhost
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$1,397 SGD
Show price breakdown
for 5 nights
$1,397 SGD for 5 nights
4.77 out of 5 average rating, 26 reviews
4.77 (26)
Top guest favourite
Guest favourite
Home in Warrensburg
River House
3 bedrooms
3 bedrooms
,
·
8 beds
8 beds
,
·
2.5 bathrooms
2.5 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,181 SGD
Show price breakdown
for 5 nights
$2,181 SGD for 5 nights
4.97 out of 5 average rating, 62 reviews
4.97 (62)
Guest favourite
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Aug
25–30 Aug
$2,602 SGD
Show price breakdown
for 5 nights
$2,602 SGD for 5 nights
4.82 out of 5 average rating, 11 reviews
4.82 (11)
Home in Chestertown
Adirondack Serenity: Pure Escape
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$2,595 SGD
Show price breakdown
for 5 nights
$2,595 SGD for 5 nights
4.2 out of 5 average rating, 10 reviews
4.2 (10)
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,518 SGD
Show price breakdown
for 5 nights
$2,518 SGD for 5 nights
New place to stay
New
1
2
3
4
…
15
