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
Oct 14 – 21
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
Jan 27 – Feb 3
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Sep 29 – Oct 6
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
Mar 16 – 23
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Jan 14 – 21
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Mar 23 – 30
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
May 9 – 16
Home in Lee
4.9 out of 5 average rating, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
Oct 18 – 25
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 11 – 18
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
Jun 18 – 25
Apartment in Greenfield
4.96 out of 5 average rating, 270 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 3 – 10
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Sep 18 – 25
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Feb 14 – 21
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Mar 8 – 15
Apartment in Bennington
4.96 out of 5 average rating, 139 reviewsCooper's Place
Jul 19 – 26
Apartment in Williamstown
4.93 out of 5 average rating, 237 reviewsCOLD SPRING
Oct 4 – 11
Condo rentals with outdoor seating
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Sep 22 – 29
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Apr 16 – 23
Condo in Saratoga Springs
4.97 out of 5 average rating, 100 reviewsUltimate Location The Belmont, Track, Broadway
May 28 – Jun 4
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Oct 3 – 10
Condo in West Dover
4.74 out of 5 average rating, 124 reviewsBeautiful condo 2.5 miles from Mount Snow
Dec 12 – 19
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
Mar 12 – 19
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Aug 4 – 11
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 2 – 9
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
G$8,361 GYD before taxes and fees
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