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 Rochester
4.97 out of 5 average rating, 182 reviewsThe Guest House at Sky Hollow
3–10 Dec
€ 180 per night
Guest favourite
Guest suite in Bethel
4.97 out of 5 average rating, 137 reviewsTwo bedroom. Separate enterence.
20–27 May
€ 135 per night
Guest favourite
Cabin in Royalton
4.99 out of 5 average rating, 174 reviewsGenuine Vermont Sugar House on 70 peaceful acres.
30 Jan – 6 Feb
€ 166 per night
Guest favourite
Flat in Rutland
4.96 out of 5 average rating, 522 reviewsYour home away from home
3–10 Jun
€ 103 per night
Guest favourite
Apartment in Killington
4.92 out of 5 average rating, 391 reviewsApril open 1 bedroom 1 night Ok Free shuttle
4–11 Jul
€ 140 per night
Guest favourite
Apartment in Killington
4.93 out of 5 average rating, 148 reviewsRenovated, w/Covered Parking-Shuttle-Walk to Lifts
21–28 Apr
€ 128 per night
Guest favourite
Cabin in Hancock
4.95 out of 5 average rating, 219 reviewsHancock hideaway
20–27 Jun
€ 166 per night
Guest favourite
Tiny home in Pittsfield
5.0 out of 5 average rating, 16 reviewsTiny Home: VT Mountain Cabin
24 Nov – 1 Dec
€ 283 per night
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
€ 112 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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- House rentals Pittsfield
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