
Pet-friendly holiday rentals in Pittsfield
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Pittsfield
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield pet-friendly home rentals
Pet-friendly house rentals

Cozy Bow House Perched in Trees w/ Hot Tub & View

Modern Farmhouse on 25 Acres - Superb Views

Modern 3-bedroom A-frame in Londonderry w/ Pond

Beautiful Woodstock Home-Perfect for entertaining

Comfortable farmhouse with stunning views

Nature Lover's Paradise

Vermont Highland

Meadow View. 35 acres outside your door!
Pet-friendly home rentals with a pool

Relax in Recreation Paradise!

Epic Views of the Green Mountains

Ranch at Mendon Mt Orchards

Moon Valley Country Retreat no clean fee pets yes

Lower Yurt Stay on VT Homestead

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Private, pet-friendly home rentals

Cabin on the Hill

Fairytale cabin at The Wild Farm

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Romantic Retreat, Hot Tub, near Killington Mtn

Ski Home Mountain Views Near Killington/Woodstock

The Guest House at Chandlery Farm

Rustic and Cozy Vermont Getaway at Sugarwood Cabin

Secluded Log Home on 109 Acre Natural Wonderland!
Quick stats about holiday rentals that are pet-friendly in Pittsfield
Total rentals
30 properties
Nightly prices starting at
₹10,447 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
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- House rentals Pittsfield
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- Pet-friendly rentals Rutland County
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Fort Ticonderoga
- Bolton Valley Resort
- Dartmouth Skiway
- Cochran's Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Dorset Field Club
- Stratton Mountain Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Vermont National Country Club
- Country Club of Vermont
- Mount Sunapee Resort
- Whaleback Mountain
- Killington Adventure Center