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Search results; Over 1,000 homes in Middlebury

Top guest favourite

Home in Middlebury

New England Charm!

1 bedroom, 1 bed, 1 private bathroom

15–20 Sept

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5.0 out of 5 average rating, 20 reviews

Guest favourite

Home in Waterbury

Come and enjoy the BURY's of CT!

2 bedrooms, 4 beds, 1 bathroom

16–21 Oct

Free cancellation

4.95 out of 5 average rating, 106 reviews

Home in Middlebury

Lake Quassapaug Homestead

2 bedrooms, 2 beds, 1 bathroom

22–27 Sept

$2,646 SGD for 5 nights

Free cancellation

4.75 out of 5 average rating, 8 reviews

Guest favourite

Flat in Middlebury

Cozy One Bedroom Apartment in Middlebury, CT

1 bedroom, 2 queen beds, 1 bathroom

20–25 Sept

$876 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 42 reviews

Top guest favourite

Home in Woodbury

Your Perfectly Wonderful Woodbury Sanctuary!

4 bedrooms, 4 beds, 2.5 bathrooms

28 Oct – 2 Nov

$2,522 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 147 reviews

Top guest favourite

Flat in Middlebury

Cozy Apartment with Water View of Brook

1 bedroom, 1 queen bed, 1 bathroom

13–18 Sept

$837 SGD for 5 nights

4.94 out of 5 average rating, 169 reviews

Guest favourite

Room in Middlebury

Cunningham Towers

2 beds, 1 bathroom

20–25 Sept

$719 SGD for 5 nights

4.83 out of 5 average rating, 42 reviews

Guest suite in Middlebury

Country Retreat Near Lake Quassapaug

1 bedroom, 3 beds, 1 bathroom

30 Sept – 7 Oct

Weekly discount

4.9 out of 5 average rating, 49 reviews

Guest favourite

Home in Waterbury

Beautiful bunker hill home with Gym and yard!

2 bedrooms, 2 beds, 1 bathroom

14–19 Sept

4.75 out of 5 average rating, 12 reviews

Guest favourite

Flat in Watertown

Steele Brook Manor

2 bedrooms, 3 beds, 1 bathroom

4–9 Oct

$905 SGD for 5 nights

4.95 out of 5 average rating, 57 reviews

Guest favourite

Home in Bethlehem

The Parish house

3 bedrooms, 3 beds, 1 bathroom

14–19 Sept

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Watertown

Cozy Cottage

2 bedrooms, 3 beds, 1 bathroom

4–9 Oct

Free cancellation

4.77 out of 5 average rating, 91 reviews

Guest favourite

Home in Watertown

Historic Litchfield County Home

5 bedrooms, 6 beds, 3.5 bathrooms

22–27 Sept

$5,036 SGD for 5 nights

Free cancellation

4.88 out of 5 average rating, 33 reviews

Top guest favourite

Home in Waterbury

Amazing views of the Brass City

3 bedrooms, 3 beds, 1.5 bathrooms

11–16 Oct

$1,372 SGD for 5 nights

4.96 out of 5 average rating, 161 reviews

Guest favourite

Home in Waterbury

Ideal for sightseeing or long stays.

3 bedrooms, 3 beds, 1 bathroom

13–18 Sept

$1,122 SGD for 5 nights

4.86 out of 5 average rating, 14 reviews

Guest favourite

Home in Woodbury

Ferris House: Private 19th Century Home

3 bedrooms, 4 beds, 1.5 bathrooms

14–19 Sept

4.94 out of 5 average rating, 107 reviews

Home in Watertown

Guest House on Country Estate

3 bedrooms, 2 queen beds, 1 bathroom

19–24 Sept

$2,069 SGD for 5 nights

4.76 out of 5 average rating, 110 reviews

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, 79 reviews

Home in Waterbury

Charming Connecticut Retreat Near Museums & Hiking

3 bedrooms, 5 beds, 1.5 bathrooms

28 Sept – 3 Oct

$1,390 SGD for 5 nights

4.6 out of 5 average rating, 20 reviews