House vacation rentals in Berkshire County
Find and book unique houses on Airbnb
Top-rated house rentals in Berkshire County
Guests agree: these houses 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 Berkshire County house rentals
House rentals with a pool
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jun 23 – 30
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Nov 15 – 22
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Sep 14 – 21
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun 9 – 16
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Mar 4 – 11
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Dec 11 – 18
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Apr 14 – 21
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Oct 27 – Nov 3
Weekly house rentals
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec 7 – 14
Home in Lenox
4.93 out of 5 average rating, 209 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep 14 – 21
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Jun 5 – 12
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 1 – 8
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
May 12 – 19
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Jan 26 – Feb 2
Home in Becket
4.86 out of 5 average rating, 287 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Nov 11 – 18
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
May 19 – 26
Private house rentals
Home in Otis
4.83 out of 5 average rating, 59 reviewsSpringtime Oasis in the Berkshires!
Jun 19 – 26
Home in Cheshire
5.0 out of 5 average rating, 22 reviewsThe Berkshires Hummingbird House
Oct 17 – 24
Home in Great Barrington
5.0 out of 5 average rating, 3 reviewsWalt's Townhouse - Berkshire living at its best
May 28 – Jun 4
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Sep 6 – 13
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
Dec 18 – 25
Home in Great Barrington
4.97 out of 5 average rating, 38 reviewsWaterfront Modern Lake Mansfield Retreat
Jan 4 – 11
Home in Becket
5.0 out of 5 average rating, 3 reviewsLakeside 3-BR Berkshires Residence
Sep 24 – Oct 1
Home in Becket
5.0 out of 5 average rating, 20 reviewsSecluded lakeside charmer
Sep 6 – 13
Destinations to explore
- House rentals United States
- Guesthouse rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- Lighthouse rentals United States
- Townhouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Guesthouse rentals New York
- Treehouse rentals New York
- Tiny house rentals Massachusetts
- Townhouse rentals Massachusetts
- House rentals Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Lakehouse rentals Massachusetts
- Tiny house rentals Massachusetts
- Townhouse rentals Massachusetts
- House rentals Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Lakehouse rentals Massachusetts
- Apartment rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Rentals with a sauna Berkshire County
- Condo rentals Berkshire County
- Hotel rentals Berkshire County
- Rentals with a washer and dryer Berkshire County
- Rentals with lake access Berkshire County
- Guesthouse rentals Berkshire County
- Rentals with a fire pit Berkshire County
- Rentals with an EV charger Berkshire County
- Cottage rentals Berkshire County
- Rentals with beach access Berkshire County
- Family-friendly rentals Berkshire County
- Boutique hotel rentals Berkshire County
- Bed and breakfasts Berkshire County
- Fitness-friendly rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Cabin rentals Berkshire County
- Private suite rentals Berkshire County
- Monthly Rentals Berkshire County
- Rentals with breakfast Berkshire County
- Farmstay rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Chalet rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with pools Berkshire County
- Rentals with a kayak Berkshire County
- Pet-friendly rentals Berkshire County
- Rentals with a patio Berkshire County
- Beachfront rentals Berkshire County
- Waterfront rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom