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 Rochester
4.95 out of 5 average rating, 144 reviewsCottage in the Heart of the Green Mountains
25 Jul – 1 Aug
Home in Pittsfield
4.83 out of 5 average rating, 221 reviewsKillington area home - 4-seasons & hot tub
31 Oct – 7 Nov
Home in Rochester
4.9 out of 5 average rating, 282 reviewsMountain Home ready for you!
16–23 Sep
Home in Rochester
4.98 out of 5 average rating, 124 reviewsModern Farmhouse on 25 Acres - Superb Views
7–14 Nov
Home in Rochester
4.94 out of 5 average rating, 181 reviewsThe McKinley House
3–10 Feb
Home in Rochester
4.93 out of 5 average rating, 202 reviewsPorch House
11–18 Jun
Home in Rutland
5.0 out of 5 average rating, 121 reviewsONE ROOM SCHOOL HOUSE
30 May – 6 Jun
Home in Tunbridge
4.98 out of 5 average rating, 315 reviewsThe Barnbrook House
16–23 Jan
Apartment rentals with outdoor seating
Flat in Tunbridge
4.92 out of 5 average rating, 219 reviewsFairview
4–11 Feb
Flat in Stockbridge
4.88 out of 5 average rating, 160 reviewsRustic 64 Acre Woodland Haven on a Beautiful River
30 Sep – 7 Oct
Flat in Chittenden
4.95 out of 5 average rating, 243 reviewsCozy Apt Close to Mountain Top Inn & Ski Areas
30 Jun – 7 Jul
Flat in Poultney
4.94 out of 5 average rating, 307 reviewsCozy Poultney Village Apartment
22–29 Jan
Flat in New Haven
4.99 out of 5 average rating, 189 reviewsDog Team Falls Apartment - Minutes from Middlebury
10–17 Apr
Flat in Clarendon
4.92 out of 5 average rating, 133 reviewsVermont Horse Farm
25 Jul – 1 Aug
Flat in Middlebury
4.99 out of 5 average rating, 103 reviewsMountain View Retreat
17–24 Jun
Flat in Salisbury
4.89 out of 5 average rating, 143 reviewsDoc's Lake House 1st floor, 2 bdrm full apartment
26 Dec – 2 Jan
Apartment rentals with outdoor seating
Apartment in Killington
4.94 out of 5 average rating, 175 reviewsWalk or Shuttle to Lifts/2BR @ Mt. Green Resort
9–16 Aug
Apartment in Killington
4.93 out of 5 average rating, 138 reviewsRenovated unit, prime location! Shuttle on/Ski off
13–20 Jul
Apartment in Ludlow
4.92 out of 5 average rating, 123 reviewsOkemo Ski-in/Ski-out, Steps to lift Condo
9–16 May
Apartment in Killington
4.94 out of 5 average rating, 152 reviewsBright Ski on/off Condo Full Kitchen-Free Shuttle!
21–28 Jul
Apartment in Killington
4.96 out of 5 average rating, 103 reviewsCozyCub Pets, AC, Bike to Mtn, Fireplace, Walk out
30 Nov – 7 Dec
Apartment in Killington
4.9 out of 5 average rating, 119 reviewsCozy & Convenient Ski Home Condo
29 Aug – 5 Sep
Apartment in Killington
4.93 out of 5 average rating, 148 reviewsRenovated, w/Covered Parking-Shuttle-Walk to Lifts
12–19 Oct
Apartment in Ludlow
4.99 out of 5 average rating, 100 reviewsUpdated Main St Condo in downtown Ludlow!
12–19 Jun
Quick stats about holiday rentals with outdoor seating in Pittsfield
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
€ 112 before taxes and fees
Destinations to explore
- Burlington Holiday rentals
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