Holiday rentals in Pittsfield
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Top-rated holiday rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield
Guest favourite
Home in Middlebury
4.99 out of 5 average rating, 356 reviewsNice one bedroom cottage
Guest favourite
Flat in Rutland
4.96 out of 5 average rating, 525 reviewsYour home away from home
Guest favourite
Cabin in Randolph
4.95 out of 5 average rating, 193 reviewsSecluded Log Home on 109 Acre Natural Wonderland!
Guest favourite
Cabin in Hancock
4.95 out of 5 average rating, 221 reviewsHancock hideaway
Guest favourite
Tiny home in Warren
4.99 out of 5 average rating, 157 reviewsLuxury Glass Tiny House - Mountain View + Hot Tub
Guest favourite
Cottage in Brandon
4.91 out of 5 average rating, 266 reviewsHenrietta’s Hideaway-Walk Downtown!
Guest favourite
Flat in Royalton
4.98 out of 5 average rating, 149 reviewsQuiet Vermont Get Away
Guest favourite
Cabin in Hancock
4.97 out of 5 average rating, 343 reviewsFunky, family-friendly cabin
Quick stats about holiday rentals in Pittsfield
Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
€ 111 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
- Lake George Holiday rentals
- Lake Placid Holiday rentals
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- Philadelphia Holiday rentals
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- Québec Holiday rentals
- Rentals with a patio Pittsfield
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- Family-friendly rentals Pittsfield
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