Vacation rentals with outdoor seating in Berkshire County

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Berkshire County

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
Feb 9 – 16
$352 per night
4.94 out of 5 average rating, 341 reviews
Superhost
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.
Apr 1 – 8
$228 per night
4.84 out of 5 average rating, 227 reviews
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
Aug 19 – 26
$109 per night
4.93 out of 5 average rating, 246 reviews

Popular amenities for Berkshire County outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Dalton
The Yellow House
Oct 7 – 14
$104 per night
4.91 out of 5 average rating, 111 reviews
Guest favorite
Home in Lee
Cozy Berkshires Cottage
May 22 – 29
$117 per night
4.89 out of 5 average rating, 233 reviews
Guest favorite
Home in Monterey
Perfect Berkshire getaway.Cozy cottage.Great wifi.
Apr 4 – 11
$115 per night
4.93 out of 5 average rating, 112 reviews
Guest favorite
Home in Canaan
Country Cottage
Dec 28 – Jan 4
$135 per night
5.0 out of 5 average rating, 129 reviews
Guest favorite
Home in Lenox
The Berkshire Quintessential Cape downtown Lenox
Nov 4 – 11
$425 per night
4.93 out of 5 average rating, 215 reviews
Guest favorite
Home in New Lebanon
The old sawmill from 1771
Dec 15 – 22
$125 per night
4.99 out of 5 average rating, 347 reviews
Guest favorite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Apr 18 – 25
$273 per night
4.92 out of 5 average rating, 168 reviews
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 23 – 30
$225 per night
4.89 out of 5 average rating, 199 reviews
Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
Dec 31 – Jan 7
$399 per night
4.96 out of 5 average rating, 134 reviews
Guest favorite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
Jun 6 – 13
$221 per night
4.93 out of 5 average rating, 203 reviews
Guest favorite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
Apr 18 – 25
$380 per night
4.99 out of 5 average rating, 118 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Sep 5 – 12
$159 per night
4.96 out of 5 average rating, 305 reviews

Apartment rentals with outdoor seating

Guest favorite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
Jan 19 – 26
$96 per night
4.95 out of 5 average rating, 313 reviews
Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
Jul 29 – Aug 5
$59 per night
4.85 out of 5 average rating, 140 reviews
Guest favorite
Apartment in Lenox
Station House 1E Private Room & Bath
May 9 – 16
$64 per night
4.88 out of 5 average rating, 168 reviews
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Nov 12 – 19
$114 per night
4.91 out of 5 average rating, 117 reviews
Guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
May 9 – 16
$138 per night
5.0 out of 5 average rating, 317 reviews
Guest favorite
Apartment in North Adams
See MoCA from your mansion+Sauna! Ski nearby!
Jan 16 – 23
$128 per night
4.97 out of 5 average rating, 388 reviews
Guest favorite
Apartment in Williamstown
New Studio In Town, By the Water
Mar 28 – Apr 4
$124 per night
4.96 out of 5 average rating, 293 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
4.83 out of 5 average rating, 151 reviews
Guest favorite
Apartment in Lenox
Lovely Downtown Lenox apt, walk to everything!
Aug 21 – 28
$425 per night
4.95 out of 5 average rating, 105 reviews
Guest favorite
Apartment in Williamstown
COLD SPRING
Jul 23 – 30
$142 per night
4.93 out of 5 average rating, 229 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
Jan 6 – 13
$120 per night
4.91 out of 5 average rating, 223 reviews
Guest favorite
Apartment in North Adams
Overlooking the city in a quiet 7 unit building.
May 2 – 9
$158 per night
4.98 out of 5 average rating, 179 reviews

Condo rentals with outdoor seating

Guest favorite
Condo in Hancock
Cozy Condo @ Jiminy Peak
Aug 18 – 25
$150 per night
4.83 out of 5 average rating, 129 reviews
Guest favorite
Condo in Hancock
Upscale 2 bed/2bath Condo at a Mountain Resort!
Nov 5 – 12
$233 per night
4.94 out of 5 average rating, 18 reviews
Guest favorite
Condo in Lenox
Spacious 3 bedroom apt in Lenox historic downtown
Oct 4 – 11
$332 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Hancock
Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Apr 26 – May 3
$461 per night
4.97 out of 5 average rating, 34 reviews
Guest favorite
Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
May 16 – 23
$151 per night
4.89 out of 5 average rating, 19 reviews
Condo in Hancock
Bentley Brook Presidents Week & Christmas
Dec 22 – 29
$379 per night
5.0 out of 5 average rating, 3 reviews
Condo in Pittsfield
Serene Retreat in the Scenic Berkshire Mountains
Dec 3 – 10
$499 per night
New place to stay
Guest favorite
Room in Great Barrington
Quiet refuge in Great Barrington
Jul 16 – 23
$43 per night
4.96 out of 5 average rating, 146 reviews

Destinations to explore