Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Tolland
Check in / Check out
Any week
Guests
Add guests
Become a host
Languages & currency
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 Tolland
Over 1,000 homes in Tolland
Guest favourite
Guest favourite
Home in Tolland
Cabin with Hot Tub and Lake Access
2 bedrooms
,
·
5 beds
,
·
2 private bathrooms
11–16 Sept
11–16 Sept
$1,459 SGD
Show price breakdown
for 5 nights
$1,459 SGD for 5 nights
,
·
4.9 out of 5 average rating, 20 reviews
4.9 (20)
Top guest favourite
Guest favourite
Home in Tolland
Lakefront Retreat at Porcupine Place
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$2,090 SGD
$1,846 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 47 reviews
5.0 (47)
Guest favourite
Guest favourite
Home in Tolland
Private Woodland Retreat by Lake | Berkshires
3 bedrooms
3 bedrooms
,
·
2 bathrooms
2 bathrooms
11–16 Sept
11–16 Sept
$1,360 SGD
$1,210 SGD
Show price breakdown
for 5 nights
4.8 out of 5 average rating, 5 reviews
4.8 (5)
Guest favourite
Guest favourite
Home in Tolland
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
9–14 Sept
9–14 Sept
$2,342 SGD
Show price breakdown
for 5 nights
$2,342 SGD for 5 nights
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Guest favourite
Guest favourite
Home in Tolland
Cozy Berkshires Lakefront Cottage! NEW
2 bedrooms
2 bedrooms
,
·
10 beds
10 beds
,
·
2.5 bathrooms
2.5 bathrooms
3–8 Jan
3–8 Jan
$2,944 SGD
Show price breakdown
for 5 nights
$2,944 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 38 reviews
4.89 (38)
Guest favourite
Guest favourite
Home in Otis
Home In Otis
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$1,943 SGD
$1,324 SGD
Show price breakdown
for 5 nights
4.92 out of 5 average rating, 53 reviews
4.92 (53)
Top guest favourite
Guest favourite
Cottage in Otis
Berkshire lakefront cabin with modern luxuries
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$3,962 SGD
Show price breakdown
for 5 nights
$3,962 SGD for 5 nights
4.98 out of 5 average rating, 94 reviews
4.98 (94)
Top guest favourite
Guest favourite
Home in Sandisfield
Lux on the River near Tanglewood w/220v EV charge
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Dec
4–9 Dec
$2,234 SGD
$1,962 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 95 reviews
4.95 (95)
Top guest favourite
Guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
13–18 Sept
13–18 Sept
$2,758 SGD
Show price breakdown
for 5 nights
$2,758 SGD for 5 nights
Free cancellation
4.82 out of 5 average rating, 82 reviews
4.82 (82)
Guest favourite
Guest favourite
Cabin in Sandisfield
Cozy Cabin in the Berkshires
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$1,931 SGD
Show price breakdown
for 5 nights
$1,931 SGD for 5 nights
4.83 out of 5 average rating, 24 reviews
4.83 (24)
Top guest favourite
Guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1.5 bathrooms
1.5 bathrooms
10–15 Sept
10–15 Sept
$1,940 SGD
$1,719 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 83 reviews
5.0 (83)
Guest favourite
Guest favourite
Home in Colebrook
Log Cabin sleeps 30 bunk style on 350 acres
30 single beds
30 single beds
,
·
2 bathrooms
2 bathrooms
16–21 Oct
16–21 Oct
$6,931 SGD
Show price breakdown
for 5 nights
$6,931 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 81 reviews
4.96 (81)
Guest favourite
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
WC
WC
12–17 Sept
12–17 Sept
$1,872 SGD
$1,638 SGD
Show price breakdown
for 5 nights
4.9 out of 5 average rating, 178 reviews
4.9 (178)
Top guest favourite
Guest favourite
Home in Otis
Ridge House at Otis Ridge Ski Area
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Sept
24–29 Sept
$2,113 SGD
$1,863 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 55 reviews
4.98 (55)
Guest favourite
Guest favourite
Cottage in Otis
The lake house
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
15–20 Sept
15–20 Sept
$1,828 SGD
Show price breakdown
for 5 nights
$1,828 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 51 reviews
4.96 (51)
Guest favourite
Guest favourite
Cabin in Otis
Enjoy 43 Acres on Two Ponds!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$3,567 SGD
$3,093 SGD
Show price breakdown
for 5 nights
4.89 out of 5 average rating, 70 reviews
4.89 (70)
Guest favourite
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,312 SGD
Show price breakdown
for 5 nights
$2,312 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Top guest favourite
Guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$1,423 SGD
Show price breakdown
for 5 nights
$1,423 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 23 reviews
4.96 (23)
Top guest favourite
Guest favourite
Home in Litchfield County
70's Retro House
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$1,448 SGD
$1,239 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 29 reviews
4.97 (29)
1
2
3
4
…
15