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
Superhost
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms
,
·
4 beds
,
·
1 shared bathroom
18–23 Aug
18–23 Aug
$1,567 SGD
Show price breakdown
for 5 nights
$1,567 SGD for 5 nights
,
·
4.85 out of 5 average rating, 41 reviews
4.85 (41)
Top guest favourite
Guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,508 SGD
Show price breakdown
for 5 nights
$1,508 SGD for 5 nights
4.96 out of 5 average rating, 267 reviews
4.96 (267)
Top guest favourite
Guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,204 SGD
Show price breakdown
for 5 nights
$3,204 SGD for 5 nights
4.93 out of 5 average rating, 182 reviews
4.93 (182)
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$2,527 SGD
Show price breakdown
for 5 nights
$2,527 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Aug
26–31 Aug
$1,823 SGD
Show price breakdown
for 5 nights
$1,823 SGD for 5 nights
5.0 out of 5 average rating, 59 reviews
5.0 (59)
Top guest favourite
Guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms
4 bedrooms
,
·
11 beds
11 beds
,
·
2.5 bathrooms
2.5 bathrooms
4–9 Oct
4–9 Oct
$5,127 SGD
Show price breakdown
for 5 nights
$5,127 SGD for 5 nights
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$2,568 SGD
Show price breakdown
for 5 nights
$2,568 SGD for 5 nights
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
13–18 Sept
13–18 Sept
$1,539 SGD
Show price breakdown
for 5 nights
$1,539 SGD for 5 nights
4.93 out of 5 average rating, 55 reviews
4.93 (55)
Guest favourite
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,051 SGD
Show price breakdown
for 5 nights
$2,051 SGD for 5 nights
4.94 out of 5 average rating, 17 reviews
4.94 (17)
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
25–30 Aug
25–30 Aug
$2,571 SGD
Show price breakdown
for 5 nights
$2,571 SGD for 5 nights
4.96 out of 5 average rating, 275 reviews
4.96 (275)
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,790 SGD
Show price breakdown
for 5 nights
$2,790 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$2,408 SGD
Show price breakdown
for 5 nights
$2,408 SGD for 5 nights
4.89 out of 5 average rating, 57 reviews
4.89 (57)
Guest favourite
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$2,576 SGD
$2,349 SGD
Show price breakdown
for 5 nights
Extended stay discount
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Top guest favourite
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,846 SGD
$2,520 SGD
Show price breakdown
for 5 nights
4.86 out of 5 average rating, 7 reviews
4.86 (7)
Guest favourite
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Oct
13–18 Oct
$1,712 SGD
Show price breakdown
for 5 nights
$1,712 SGD for 5 nights
4.88 out of 5 average rating, 60 reviews
4.88 (60)
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
5–10 Sept
5–10 Sept
$2,533 SGD
Show price breakdown
for 5 nights
$2,533 SGD for 5 nights
4.88 out of 5 average rating, 16 reviews
4.88 (16)
Guest favourite
Guest favourite
Cabin in Chestertown
Meadow House
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3 bathrooms
3 bathrooms
23–28 Aug
23–28 Aug
$2,285 SGD
Show price breakdown
for 5 nights
$2,285 SGD for 5 nights
4.88 out of 5 average rating, 166 reviews
4.88 (166)
Cabin in Chestertown
All-Season Family Retreat w/ Dock on Loon Lake!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$2,728 SGD
Show price breakdown
for 5 nights
$2,728 SGD for 5 nights
Top guest favourite
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms
2 bedrooms
,
·
2 bathrooms
2 bathrooms
22–29 Aug
22–29 Aug
$1,682 SGD
$1,369 SGD
Show price breakdown
for 7 nights
Weekly discount
4.96 out of 5 average rating, 45 reviews
4.96 (45)
1
2
3
4
…
15
