Vacation rentals with outdoor seating in Pittsfield
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Pittsfield
Guests agree: these accommodations with outdoor seating 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 outdoor seating rentals
House rentals with outdoor seating
Home in Becket
4.92 out of 5 average rating, 106 reviewsBeautiful, quiet and cozy home in Becket!
Home in Lenox
4.88 out of 5 average rating, 137 reviewsColonial House, w/Yard,7min walk to Downtown Lenox
Home in Becket
4.93 out of 5 average rating, 131 reviewsLake front retreat - Stylish Berkshire home
Home in Lee
4.9 out of 5 average rating, 222 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Canaan
5 out of 5 average rating, 149 reviewsCountry Cottage
Home in Becket
4.87 out of 5 average rating, 313 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Catskill
4.96 out of 5 average rating, 103 reviewsCheerful Catskill Village Cottage
Home in Craryville
4.91 out of 5 average rating, 100 reviewsThe Gatehouse at Raspberry Ridge
Apartment rentals with outdoor seating
Rental unit in Shelburne Falls
4.97 out of 5 average rating, 516 reviewsIn town, newly renovated studio with private deck
Rental unit in Hillsdale
4.98 out of 5 average rating, 187 reviewsSerene Suite by Brewery Zipline Berkshires Hudson
Rental unit in Northampton
4.94 out of 5 average rating, 308 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Rental unit in Northampton
4.92 out of 5 average rating, 575 reviewsSunny Peaceful Home
Rental unit in Bennington
4.95 out of 5 average rating, 150 reviewsCooper's Place
Rental unit in Williamstown
4.93 out of 5 average rating, 271 reviewsCOLD SPRING
Rental unit in Northampton
4.98 out of 5 average rating, 675 reviewsTree Top Suite, cozy downtown apartment
Rental unit in Sheffield
5 out of 5 average rating, 337 reviewsHideaway with Spectacular Berkshire Views
Condo rentals with outdoor seating
Condo in West Dover
4.74 out of 5 average rating, 129 reviewsBeautiful condo 2.5 miles from Mount Snow
Condo in Hancock
4.98 out of 5 average rating, 42 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Condo in Lenox
5 out of 5 average rating, 27 reviewsSpacious 3 bedroom apt in Lenox historic downtown
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Northampton
4.93 out of 5 average rating, 84 reviewsCozy Studio with patio, 1.2 mi from downtown
Condo in Dover
4.94 out of 5 average rating, 32 reviewsSki in Ski out condo great location
Condo in Dover
4.96 out of 5 average rating, 70 reviewsCozy Mt Snow Ski In / Out
Condo in Hudson
4.94 out of 5 average rating, 175 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Quick stats about vacation rentals with outdoor seating in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$68 CAD before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
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