Vacation rentals in Middlebury
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Top-rated vacation rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury
Guest favorite
Apartment in Southbury
4.87 out of 5 average rating, 87 reviewsSuite Hill studio
Dec 23 – 30
ﺩ.ﺇ513 per night
Guest favorite
Guesthouse in Newtown
4.79 out of 5 average rating, 19 reviewsCozy Stay in Newtown - discounts for long term
Sep 25 – Oct 2
ﺩ.ﺇ396 per night
Guest favorite
Loft in Woodbury
5.0 out of 5 average rating, 31 reviewsCountry Loft
Jan 27 – Feb 3
ﺩ.ﺇ536 per night
Guest favorite
Home in Southbury
5.0 out of 5 average rating, 55 reviewsThe Cottage at Cedar Spring Farm
Aug 12 – 19
ﺩ.ﺇ590 per night
Guest favorite
Apartment in Waterbury
4.95 out of 5 average rating, 19 reviewsFunky downtown art studio apartment.
Jul 26 – Aug 2
ﺩ.ﺇ376 per night
Guest favorite
Farm stay in Bethlehem
5.0 out of 5 average rating, 10 reviewsThe Loft @ Sun One Organic Farm
Feb 12 – 19
ﺩ.ﺇ295 per night
Guest favorite
Guesthouse in Southbury
4.96 out of 5 average rating, 51 reviewsThe Nest. Large studio in the Woods.
May 2 – 9
ﺩ.ﺇ522 per night
Guest favorite
Guesthouse in Sharon
5.0 out of 5 average rating, 64 reviewsCottage with a Waterfall View
Sep 26 – Oct 3
ﺩ.ﺇ400 per night
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