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Search results; Over 1,000 places

Guest favourite
Flat in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
1–6 Apr
4.92 out of 5 average rating, 24 reviews
Superhost
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
Individual Host
28 Apr – 3 May
4.86 out of 5 average rating, 137 reviews
Guest favourite
Guest house in Lenox
Guest House at Stonover Estate
1 queen bed
2–7 May
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Pittsfield
Modern Gem in the Heart of Berkshires
Individual Host
1–6 Apr
4.9 out of 5 average rating, 10 reviews
Guest favourite
Cottage in Becket
Cozy lakeside cottage
Individual Host
21–26 Apr
4.95 out of 5 average rating, 122 reviews
Guest favourite
Guest suite in South Lee
Sunny Riverside Apartment
Individual Host
1–6 Apr
4.92 out of 5 average rating, 189 reviews
Guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
Individual Host
1–6 Apr
4.95 out of 5 average rating, 314 reviews
Guest favourite
Tiny home in Tyringham
Enchanted Tiny Tower nestled in the Berkshires
Individual Host
7–12 Apr
4.97 out of 5 average rating, 294 reviews
Guest favourite
Home in Canaan
Private Retreat! Hot Tub, Pool Table & Movie Room
Individual Host
12–17 May
5.0 out of 5 average rating, 9 reviews
Guest favourite
Guest house in Lenox
Bella Rena Guesthouse
4 beds
6–11 May
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Lee
Stay with Andrea & BobWeb designer,
Warm & Welcoming Room w/ Private Bath
1–6 AprIndividual Host,
4.97 out of 5 average rating, 192 reviews
Guest favourite
Campervan/Motorhome in Lee
"Glamping" getaway in the beautiful Berkshires
Individual Host
1–6 May
5.0 out of 5 average rating, 117 reviews
Guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
Individual Host
1–6 Apr
4.93 out of 5 average rating, 15 reviews
Guest favourite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
7–12 AprIndividual Host,
4.99 out of 5 average rating, 374 reviews
Guest favourite
Cottage in New Lebanon
Stylish Working Farm Cottage
Professional Host
1–6 Apr
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 bed
1–6 Apr
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Canaan
Country Cottage
Individual Host
15–20 Oct
5.0 out of 5 average rating, 132 reviews
Guest favourite
Home in New Lebanon
The old sawmill from 1771
Professional Host
2–7 Apr
4.99 out of 5 average rating, 347 reviews