We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Middlebury

Photo 1 of 22

Top guest favourite

Home in Middlebury

New England Charm!

1 bedroom, 1 bed, 1 private bathroom

15–20 Sept

,

5.0 out of 5 average rating, 20 reviews

Photo 1 of 16

Guest favourite

Home in Waterbury

Come and enjoy the BURY's of CT!

2 bedrooms, 4 beds, 1 bathroom

27 Sept – 2 Oct

$1,418 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 105 reviews

Photo 1 of 6

Featured hotel

Room in Southbury

Double room

2 double beds, 1 bathroom

1–6 Sept

$1,368 SGD for 5 nights

+$188 SGD Airbnb credit

Photo 1 of 21

Home in Middlebury

Lake Quassapaug Homestead

2 bedrooms, 2 beds, 1 bathroom

2–7 Sept

$2,654 SGD for 5 nights

4.75 out of 5 average rating, 8 reviews

Photo 1 of 29

Guest favourite

Home in Waterbury

Beautiful bunker hill home with Gym and yard!

2 bedrooms, 2 beds, 1 bathroom

7–12 Sept

$1,341 SGD for 5 nights

4.82 out of 5 average rating, 11 reviews

Photo 1 of 6

Superhost

Room in Middlebury

Cunningham Towers

2 beds, 1 bathroom

4–9 Sept

$721 SGD for 5 nights

4.83 out of 5 average rating, 42 reviews

Photo 1 of 23

Guest favourite

Home in Bethlehem

The Parish house

3 bedrooms, 3 beds, 1 bathroom

3–8 Sept

$1,793 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Photo 1 of 27

Guest favourite

Flat in Middlebury

Cozy One Bedroom Apartment in Middlebury, CT

1 bedroom, 2 queen beds, 1 bathroom

20–25 Sept

$879 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 41 reviews

Photo 1 of 29

Top guest favourite

Flat in Middlebury

Cozy Apartment with Water View of Brook

1 bedroom, 1 queen bed, 1 bathroom

6–11 Sept

4.94 out of 5 average rating, 168 reviews

Photo 1 of 29

Guest favourite

Home in Watertown

Historic Litchfield County Home

5 bedrooms, 6 beds, 3.5 bathrooms

3–8 Sept

$5,180 SGD for 5 nights

4.88 out of 5 average rating, 33 reviews

Photo 1 of 29

Guest favourite

Home in Bethlehem

Nature’s Nest: Cozy Woodland Escape for Friends

3 bedrooms, 3 beds, 2.5 bathrooms

14–19 Sept

$2,622 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 22 reviews

Photo 1 of 18

Guest favourite

Home in Watertown

Cozy Cottage

2 bedrooms, 3 beds, 1 bathroom

13–18 Sept

Free cancellation

4.77 out of 5 average rating, 90 reviews

Photo 1 of 27

Guest favourite

Flat in Watertown

Steele Brook Manor

2 bedrooms, 3 beds, 1 bathroom

5–10 Sept

$991 SGD for 5 nights

4.95 out of 5 average rating, 55 reviews

Photo 1 of 29

Home in Woodbury

Nature & Luxury @Lavender Lake Est (Kosher option)

6 bedrooms, 11 beds, 5.5 bathrooms

8–13 Sept

$17,642 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Photo 1 of 7

Guest favourite

Home in Woodbury

Ferris House: Private 19th Century Home

3 bedrooms, 4 beds, 1.5 bathrooms

2–7 Sept

4.94 out of 5 average rating, 107 reviews

Photo 1 of 29

Top guest favourite

Home in Oxford

Lakefront Summer Oasis - kayak, fish and get cozy!

3 bedrooms, 6 beds, 2 bathrooms

20–25 Sept

4.97 out of 5 average rating, 78 reviews

Photo 1 of 29

Guest favourite

Flat in Waterbury

Home away from home

2 bedrooms, 2 queen beds, 1 bathroom

1–6 Sept

$897 SGD for 5 nights

4.92 out of 5 average rating, 111 reviews

Photo 1 of 29

Top guest favourite

Cabin in Woodbury

The Cozy Cabin By The Brook

3 bedrooms, 3 beds, 1 bathroom

13–18 Sept

Free cancellation

5.0 out of 5 average rating, 13 reviews

Photo 1 of 29

Guest favourite

Home in Cheshire

The Ideal Connecticut Getaway.

4 bedrooms, 5 beds, 2 bathrooms

7–12 Sept

Free cancellation

5.0 out of 5 average rating, 6 reviews