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
$2,288 SGD
$2,071 SGD
Show price breakdown
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
4.95 out of 5 average rating, 259 reviews
4.95 (259)
,
·
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
Top guest favourite
Guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 55 reviews
5.0 (55)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$1,900 SGD
Show price breakdown
for 5 nights
$1,900 SGD for 5 nights
Top guest favourite
Guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 267 reviews
4.96 (267)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$2,295 SGD
$1,689 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.93 out of 5 average rating, 15 reviews
4.93 (15)
,
·
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
23–28 Aug
23–28 Aug
$2,075 SGD
Show price breakdown
for 5 nights
$2,075 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
5.0 out of 5 average rating, 10 reviews
5.0 (10)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Jul
26–31 Jul
$2,298 SGD
Show price breakdown
for 5 nights
$2,298 SGD for 5 nights
Guest favourite
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.92 out of 5 average rating, 39 reviews
4.92 (39)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$2,213 SGD
Show price breakdown
for 5 nights
$2,213 SGD for 5 nights
Guest favourite
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
4.9 out of 5 average rating, 10 reviews
4.9 (10)
,
·
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,341 SGD
Show price breakdown
for 5 nights
$2,341 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 66 reviews
4.97 (66)
,
·
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
Top guest favourite
Guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4.98 out of 5 average rating, 174 reviews
4.98 (174)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
17–22 Oct
17–22 Oct
$2,591 SGD
Show price breakdown
for 5 nights
$2,591 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4.98 out of 5 average rating, 65 reviews
4.98 (65)
,
·
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
29 Jul – 3 Aug
29 Jul – 3 Aug
$3,814 SGD
Show price breakdown
for 5 nights
$3,814 SGD for 5 nights
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
4.89 out of 5 average rating, 55 reviews
4.89 (55)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,471 SGD
Show price breakdown
for 5 nights
$2,471 SGD for 5 nights
Guest favourite
Guest favourite
Home in Brant Lake
Cottage on Brant Lake
5.0 out of 5 average rating, 12 reviews
5.0 (12)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,458 SGD
Show price breakdown
for 5 nights
$1,458 SGD for 5 nights
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
6–11 Jul
6–11 Jul
$2,025 SGD
Show price breakdown
for 5 nights
$2,025 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Chestertown
Rita's Place
5.0 out of 5 average rating, 23 reviews
5.0 (23)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
7–12 Jul
7–12 Jul
$2,365 SGD
Show price breakdown
for 5 nights
$2,365 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4.88 out of 5 average rating, 60 reviews
4.88 (60)
,
·
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
16–21 Oct
16–21 Oct
$1,798 SGD
Show price breakdown
for 5 nights
$1,798 SGD for 5 nights
Superhost
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
4.68 out of 5 average rating, 260 reviews
4.68 (260)
,
·
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
19–24 Jul
19–24 Jul
$1,497 SGD
Show price breakdown
for 5 nights
$1,497 SGD for 5 nights
Guest favourite
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 21 reviews
5.0 (21)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
18–23 Jul
18–23 Jul
$2,663 SGD
Show price breakdown
for 5 nights
$2,663 SGD for 5 nights
Guest favourite
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4.89 out of 5 average rating, 38 reviews
4.89 (38)
,
·
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
1
2
3
4
…
15