Holiday rentals with outdoor seating in Pittsfield
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Pittsfield
Guests agree: these rentals with outdoor seating 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 outdoor seating rentals in Pittsfield
House rentals with outdoor seating
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
14–21 Oct
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
28 Sep – 5 Oct
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
4–11 Jan
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
4–11 Jan
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
5–12 Dec
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
18–25 Oct
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
19–26 Oct
Home in Southwick
4.99 out of 5 average rating, 181 reviewsLinny's Lakeview Cottage
9–16 Dec
Apartment rentals with outdoor seating
Flat in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
7–14 Oct
Flat in North Adams
4.96 out of 5 average rating, 422 reviewsSteps to MoCA, 2bd + SAUNA!
12–19 Apr
Flat in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
20–27 Jun
Flat in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
30 Mar – 6 Apr
Flat in Greenfield
4.96 out of 5 average rating, 270 reviewsMohawk Trail View/ private apt. no cleaning Fee
3–10 Jul
Flat in Bennington
4.96 out of 5 average rating, 139 reviewsCooper's Place
22–29 Aug
Flat in Northampton
4.98 out of 5 average rating, 649 reviewsTree Top Suite, cozy downtown apartment
13–20 Apr
Flat in Williamstown
4.93 out of 5 average rating, 237 reviewsCOLD SPRING
4–11 Oct
Apartment rentals with outdoor seating
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
19–26 Mar
Apartment in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
23–30 Dec
Apartment in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
18–25 Sep
Apartment in Saratoga Springs
4.97 out of 5 average rating, 100 reviewsUltimate Location The Belmont, Track, Broadway
28 Aug – 4 Sep
Apartment in West Dover
4.74 out of 5 average rating, 124 reviewsBeautiful condo 2.5 miles from Mount Snow
12–19 Dec
Apartment in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
12–19 Mar
Apartment in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
3–10 Aug
Apartment in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
1–8 Dec
Quick stats about holiday rentals with outdoor seating in Pittsfield
Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.5T reviews
Nightly prices starting at
₹3,336 before taxes and fees
Destinations to explore
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