Holiday houses 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 Bethel
4.85 out of 5 average rating, 130 reviewsHike, run, swim or cycle in beautiful Central VT
22–29 Oct
$240 NZD per night
Guest favourite
Condo in Killington
4.89 out of 5 average rating, 204 reviewsKillington-Pico ski in/out Studio at base of Pico
30 May – 6 Jun
$225 NZD per night
Guest favourite
Tiny home in Warren
4.99 out of 5 average rating, 154 reviewsLuxury Glass Tiny House - Mountain View + Hot Tub
16–23 Oct
$1,378 NZD per night
Guest favourite
Home in Killington
4.92 out of 5 average rating, 166 reviewsCozy Condo Tucked in the Heart of Killington
7–14 Jun
$298 NZD per night
Guest favourite
Home in Middlebury
4.99 out of 5 average rating, 355 reviewsNice one bedroom cottage
6–13 Nov
$244 NZD per night
Guest favourite
Cabin in Hancock
4.95 out of 5 average rating, 221 reviewsHancock hideaway
10–17 May
$291 NZD per night
Guest favourite
Condo in Killington
4.94 out of 5 average rating, 176 reviewsWalk or Shuttle to Lifts/2BR @ Mt. Green Resort
16–23 Aug
$305 NZD per night
Guest favourite
Apartment in Royalton
4.98 out of 5 average rating, 149 reviewsQuiet Vermont Get Away
25 Nov – 2 Dec
$221 NZD 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
$200 NZD 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 City Holiday rentals
- Québec Holiday rentals
- Rentals with outdoor seating Pittsfield
- Pet-friendly rentals Pittsfield
- House rentals Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Rentals with a patio Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Monthly Rentals Pittsfield
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