Vacation rentals with outdoor seating in Pittsfield
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Pittsfield
Guests agree: these outdoor seating rentals 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 Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Nov 8 – 15
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
Nov 18 – 25
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Oct 1 – 8
Home in Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
Mar 17 – 24
Home in Lee
4.9 out of 5 average rating, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 30 – Oct 7
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Dec 8 – 15
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Oct 24 – 31
Home in Bennington
4.99 out of 5 average rating, 238 reviewsCozy Modern Sugar House with spectacular views.
Feb 7 – 14
Apartment rentals with outdoor seating
Apartment in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Oct 9 – 16
Apartment in North Adams
4.96 out of 5 average rating, 424 reviewsSteps to MoCA, 2bd + SAUNA!
Jan 15 – 22
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Feb 20 – 27
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
Aug 31 – Sep 7
Apartment in Greenfield
4.96 out of 5 average rating, 272 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 25 – Aug 1
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Oct 7 – 14
Apartment in Bennington
4.96 out of 5 average rating, 140 reviewsCooper's Place
Aug 25 – Sep 1
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Nov 10 – 17
Condo rentals with outdoor seating
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Apr 7 – 14
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Aug 21 – 28
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 17 – 24
Condo in Saratoga Springs
4.97 out of 5 average rating, 100 reviewsUltimate Location The Belmont, Track, Broadway
Aug 27 – Sep 3
Condo in West Dover
4.74 out of 5 average rating, 124 reviewsBeautiful condo 2.5 miles from Mount Snow
Sep 23 – 30
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Jan 30 – Feb 6
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 27 – Aug 3
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 4 – 11
Quick stats about vacation 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
3.5K reviews
Nightly prices starting at
$40 before taxes and fees
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