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
Townhouse in Killington
4.93 out of 5 average rating, 205 reviewsDogs Welcome! - Spa Onsite w/Pool, Hot Tub 2BD/2BA
Guest favourite
Cottage in Brandon
4.91 out of 5 average rating, 267 reviewsHenrietta’s Hideaway-Walk Downtown!
Guest favourite
Cabin in Royalton
4.99 out of 5 average rating, 175 reviewsGenuine Vermont Sugar House on 70 peaceful acres.
Guest favourite
Home in Bethel
4.85 out of 5 average rating, 131 reviewsHike, run, swim or cycle in beautiful Central VT
Guest favourite
Home in Pittsfield
4.93 out of 5 average rating, 41 reviewsHideaway Mountain at Killington
Superhost
Home in Pittsfield
5.0 out of 5 average rating, 3 reviewsRomantic cozy retreat near Killington Mtn
Guest favourite
Tiny home in Pittsfield
5.0 out of 5 average rating, 19 reviewsTiny Home: VT Mountain Cabin
Guest favourite
Guest suite in Stockbridge
5.0 out of 5 average rating, 85 reviewsStudio Suite with Vermont Style & Amazing Views
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
2.8T reviews
Nightly prices starting at
₹9,972 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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- Québec Holiday rentals
- Rentals with a patio Pittsfield
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- Rentals with a washing machine and dryer Pittsfield
- Family-friendly rentals Pittsfield
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- Pet-friendly rentals Pittsfield
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