Vacation rentals in Stockbridge
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Top-rated vacation rentals in Stockbridge
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 Stockbridge vacation rentals
Other great vacation rentals in Stockbridge
Guest favourite
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
May 14 – 21
$236 CAD per night
Guest favourite
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
Dec. 18 – 25
$189 CAD per night
Guest favourite
Guest suite in Valatie
4.98 out of 5 average rating, 230 reviewsGuest Suite in Old Chatham Hunt Country
Sep. 27 – Oct. 4
$135 CAD per night
Guest favourite
Home in Lee
5.0 out of 5 average rating, 230 reviewsBerkshire Mountain retreat with Urban eco-luxuries
May 27 – Jun. 1
$567 CAD per night
Guest favourite
Cottage in West Stockbridge
4.98 out of 5 average rating, 107 reviewsHistoric 1810 Farmhouse - Fully Renovated
Jul. 19 – 26
$546 CAD per night
Guest favourite
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
Feb. 27 – Mar. 6
$211 CAD per night
Guest favourite
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Mar. 9 – 16
$179 CAD per night
Guest favourite
Guest suite in Hancock
4.83 out of 5 average rating, 154 reviewsCozy apartment near Jiminy Peak
May 6 – 13
$107 CAD per night
Quick stats about vacation rentals in Stockbridge
Total rentals
130 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
3.6K reviews
Nightly prices starting at
$137 CAD before taxes and fees
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