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 Middlebury
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 Middlebury
Over 1,000 homes in Middlebury
Top guest favourite
Guest favourite
Flat in Middlebury
Cozy Apartment with Water View of Brook
1 bedroom
,
·
1 bed
,
·
1 private bathroom
17–22 Aug
17–22 Aug
$878 SGD
Show price breakdown
for 5 nights
$878 SGD for 5 nights
,
·
4.94 out of 5 average rating, 165 reviews
4.94 (165)
Top guest favourite
Guest favourite
Home in Middlebury
New England Charm!
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
28 Aug – 2 Sept
28 Aug – 2 Sept
$1,662 SGD
Show price breakdown
for 5 nights
$1,662 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Superhost
Superhost
Room in Middlebury
Cunningham Towers
2 beds
2 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$748 SGD
Show price breakdown
for 5 nights
$748 SGD for 5 nights
4.82 out of 5 average rating, 39 reviews
4.82 (39)
Guest favourite
Guest favourite
Home in Waterbury
Beautiful bunker hill home with Gym and yard!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$1,351 SGD
Show price breakdown
for 5 nights
$1,351 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Guest favourite
Guest favourite
Cabin in Woodbury
Cozy Cabin By The Brook One
1 bedroom
1 bedroom
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,637 SGD
Show price breakdown
for 5 nights
$1,637 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Flat in Watertown
Steele Brook Manor
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,130 SGD
$938 SGD
Show price breakdown
for 5 nights
4.94 out of 5 average rating, 52 reviews
4.94 (52)
Top guest favourite
Guest favourite
Guest suite in Woodbury
NewEngland Apart/Woodbury Bike trail&Peaceful!
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$842 SGD
Show price breakdown
for 5 nights
$842 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 41 reviews
4.98 (41)
Guest favourite
Guest favourite
Home in Bethlehem
Nature’s Nest: Cozy Woodland Escape for Friends
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–20 Aug
15–20 Aug
$2,568 SGD
Show price breakdown
for 5 nights
$2,568 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Superhost
Superhost
Flat in Waterbury
Home away from home
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
13–18 Aug
13–18 Aug
$960 SGD
Show price breakdown
for 5 nights
$960 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 108 reviews
4.92 (108)
Guest favourite
Guest favourite
Home in Waterbury
Come and enjoy the BURY's of CT!
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$1,428 SGD
Show price breakdown
for 5 nights
$1,428 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 105 reviews
4.95 (105)
Top guest favourite
Guest favourite
Barn in Roxbury
Fully Renovated Rural Barn
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
23–28 Aug
23–28 Aug
$1,493 SGD
Show price breakdown
for 5 nights
$1,493 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 106 reviews
5.0 (106)
Home in Middlebury
Lake Quassapaug Homestead
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Aug
12–17 Aug
$2,690 SGD
Show price breakdown
for 5 nights
$2,690 SGD for 5 nights
Free cancellation
4.75 out of 5 average rating, 8 reviews
4.75 (8)
Guest favourite
Guest favourite
Holiday home in Woodbury
UNIQUE and GORGEOUS historic loft style rental
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
18–23 Aug
18–23 Aug
$963 SGD
$791 SGD
Show price breakdown
for 5 nights
4.87 out of 5 average rating, 62 reviews
4.87 (62)
Hotel room in Southbury
Wyndham Southbury | King | Near I-84
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$799 SGD
$706 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Guest suite in Watertown
Private King suite w/ separate entry-Walk to Taft!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,574 SGD
Show price breakdown
for 5 nights
$1,574 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 101 reviews
4.98 (101)
Guest favourite
Guest favourite
Home in Woodbury
Ferris House: Private 19th Century Home
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
12–17 Aug
12–17 Aug
$1,911 SGD
Show price breakdown
for 5 nights
$1,911 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 107 reviews
4.94 (107)
Top guest favourite
Guest favourite
Flat in Middlebury
Cozy One Bedroom Apartment in Middlebury, CT
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
15–20 Sept
15–20 Sept
$906 SGD
Show price breakdown
for 5 nights
$906 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 40 reviews
4.98 (40)
Top guest favourite
Guest favourite
Home in Southbury
The Cottage at Cedar Spring Farm
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$1,132 SGD
Show price breakdown
for 5 nights
$1,132 SGD for 5 nights
4.98 out of 5 average rating, 172 reviews
4.98 (172)
Guest favourite
Guest favourite
Guest suite in Watertown
Modern Ranch style apartment.
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$735 SGD
Show price breakdown
for 5 nights
$735 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 51 reviews
4.84 (51)
1
2
3
4
…
15