House vacation rentals in Pittsfield
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Top-rated house rentals in Pittsfield
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield house rentals
House rentals with a pool
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
Home in Plainfield
4.89 out of 5 average rating, 120 reviewsHistoric Home on 17 acres of land. Go escape!
Home in Warren
4.81 out of 5 average rating, 107 reviewsCharming Sugarbush Standalone Condo
Home in Killington
5.0 out of 5 average rating, 30 reviews* Slope Side Sauna w/ Shuttle *
Home in Killington
4.98 out of 5 average rating, 46 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Home in Killington
4.99 out of 5 average rating, 99 reviewsSugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Home in Chittenden
4.9 out of 5 average rating, 81 reviewsComfortable, relaxing large country home
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
Weekly house rentals
Home in Rochester
4.93 out of 5 average rating, 202 reviewsPorch House
Home in Ripton
4.89 out of 5 average rating, 257 reviewsCozy cottage near nature
Home in Killington
4.94 out of 5 average rating, 125 reviewsAtelier Killington, hottub and amazing location
Home in Clarendon
4.96 out of 5 average rating, 249 reviewsCustom 2BR Vacation Retreat in Killington Valley!
Home in Woodstock
5.0 out of 5 average rating, 110 reviewsBeautiful Woodstock Home-Perfect for entertaining
Home in Rutland
4.81 out of 5 average rating, 292 reviewsHome Sweet Home
Home in Killington
4.95 out of 5 average rating, 111 reviewsCozy Private House on Killington Mtn - Hottub
Home in Killington
4.88 out of 5 average rating, 216 reviewsTanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ
Private house rentals
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsHideaway Mountain at Killington
Home in Pittsfield
4.86 out of 5 average rating, 90 reviewsA million-dollar view near Killington on 60 acres.
Home in Rochester
5.0 out of 5 average rating, 42 reviewsSecluded Oasis: Sugarbush, Killington, Mtn Biking
Home in Hancock
4.91 out of 5 average rating, 89 reviewsThe Branch House | between Sugarbush & Killington
Home in Pittsfield
4.93 out of 5 average rating, 15 reviewsBeautiful Cabin w/Hot Tub by #1 Golf Course in VT
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
Home in Pittsfield
5.0 out of 5 average rating, 9 reviewsMountain Top - Fresh Pond - Killington - Hot Tub
Home in Pittsfield
4.9 out of 5 average rating, 20 reviewsThe Getaway, Killington. Four Bedroom with Hot Tub
Quick stats about house rentals in Pittsfield
Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$230 before taxes and fees
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