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 Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
Aug. 11 – 18
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
Sep. 10 – 17
Home in Plainfield
4.89 out of 5 average rating, 118 reviewsHistoric Home on 17 acres of land. Go escape!
Oct. 13 – 20
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
May 9 – 16
Home in Warren
4.81 out of 5 average rating, 107 reviewsCharming Sugarbush Standalone Condo
May 15 – 22
Home in Killington
4.97 out of 5 average rating, 30 reviewsSnowflake- Pool, Hot Tub, Wood Burning Fireplace
May 2 – 9
Home in Killington
4.98 out of 5 average rating, 45 reviewsGlamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Jul. 6 – 13
Home in Killington
5.0 out of 5 average rating, 27 reviews* Slope Side Sauna w/ Shuttle *
Jun. 25 – Jul. 2
Weekly house rentals
Home in Roxbury
4.9 out of 5 average rating, 157 reviewsCaptain Tom's Cabin - Secluded Vermont Getaway
Aug. 21 – 28
Home in Rutland
5.0 out of 5 average rating, 121 reviewsONE ROOM SCHOOL HOUSE
Sep. 9 – 16
Home in Tunbridge
4.98 out of 5 average rating, 314 reviewsThe Barnbrook House
Jan. 6 – 13
Home in Fairlee
4.96 out of 5 average rating, 408 reviewsCozy Bow House Perched in Trees w/ Hot Tub & View
Dec. 19 – 26
Home in Lincoln
4.98 out of 5 average rating, 172 reviewsModern Home in Lincoln on 13 ac W/ Lvl 2 Charger
May 5 – 12
Home in S Londonderry
4.95 out of 5 average rating, 270 reviewsCozy barn apartment in So. Vermont
Jan. 28 – Feb. 4
Home in Newbury
4.97 out of 5 average rating, 114 reviewsWright’s Mountain Retreat with Sauna
Sep. 19 – 26
Home in Hartford
4.95 out of 5 average rating, 130 reviewsThe Quechee Haus: VT Retreat with Outdoor Hot Tub
Apr. 7 – 14
Private house rentals
Home in Stockbridge
4.87 out of 5 average rating, 134 reviewsEscape to Vermont
Jul. 15 – 22
Home in South Londonderry
4.86 out of 5 average rating, 99 reviewsLovers Honey Pond Treehouse with hot tub & sauna
Mar. 5 – 12
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsHideaway Mountain at Killington
Jun. 3 – 10
Home in Hancock
4.91 out of 5 average rating, 89 reviewsThe Branch House | between Sugarbush & Killington
Dec. 9 – 16
Home in Pittsfield
4.86 out of 5 average rating, 90 reviewsA million-dollar view near Killington on 60 acres.
Jul. 30 – Aug. 6
Home in Barnard
4.98 out of 5 average rating, 90 reviewsThe Looking Glass, a modernistic escape
Feb. 17 – 24
Home in Rochester
5.0 out of 5 average rating, 42 reviewsSecluded Oasis: Sugarbush, Killington, Mtn Biking
Oct. 12 – 19
Home in Pittsfield
4.93 out of 5 average rating, 15 reviewsBeautiful Cabin w/Hot Tub by #1 Golf Course in VT
Nov. 27 – Dec. 4
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
$314 CAD before taxes and fees
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