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, 311 reviewsRiverfront Getaway
Dec 7 – 14
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
Dec 16 – 23
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Mar 31 – Apr 7
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Feb 15 – 22
Home in Dalton
4.99 out of 5 average rating, 120 reviewsCleveland House - renovated Berkshires' gem.
Nov 3 – 10
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 2 – 9
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Nov 21 – 28
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec 8 – 15
Apartment rentals with outdoor seating
Apartment in Copake Falls
4.93 out of 5 average rating, 258 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Sep 13 – 20
Apartment in Bennington
4.93 out of 5 average rating, 527 reviewsThe Octopus's Garden
Aug 6 – 13
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Dec 31 – Jan 7
Apartment in Bennington
4.96 out of 5 average rating, 139 reviewsCooper's Place
Jul 11 – 18
Apartment in Greenfield
4.96 out of 5 average rating, 270 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 3 – 10
Apartment in Williamstown
4.93 out of 5 average rating, 236 reviewsCOLD SPRING
Sep 23 – 30
Apartment in Northampton
4.98 out of 5 average rating, 647 reviewsTree Top Suite, cozy downtown apartment
Dec 19 – 26
Apartment in Niskayuna
5.0 out of 5 average rating, 108 reviewsNiskayuna One Bedroom Chalet
Jun 17 – 24
Condo rentals with outdoor seating
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 30 – Jun 6
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Oct 29 – Nov 5
Condo in West Dover
4.74 out of 5 average rating, 124 reviewsBeautiful condo 2.5 miles from Mount Snow
Oct 29 – Nov 5
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 7 – 14
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
Sep 22 – 29
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Oct 8 – 15
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Oct 12 – 19
Condo in Dover
4.96 out of 5 average rating, 23 reviewsSki in Ski out condo great location
Jun 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
$40 before taxes and fees
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