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Search results; Over 1,000 places in Monterey

Guest favorite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 beds
Apr 7 – 12
5.0 out of 5 average rating, 27 reviews
Guest favorite
Guesthouse in Lee
The Justice's Birthplace - 1815 Berkshires House
2 beds
Apr 1 – 6
4.91 out of 5 average rating, 53 reviews
Superhost
Apartment in Stockbridge
Historic Retreat
1 queen bed
Apr 1 – 6
4.88 out of 5 average rating, 26 reviews
Cottage in New Marlborough
Berkshires Bliss. Simplicity. Rest. Reset.
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 5 reviews
Guest favorite
Bungalow in Hillsdale
Copake Lake & Catamount/Berkshires Cottage
2 queen beds
Apr 1 – 6
4.86 out of 5 average rating, 129 reviews
Guest favorite
Apartment in Canaan
Queechy Lake Carriage House
2 beds
Apr 1 – 6
4.96 out of 5 average rating, 79 reviews
Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
6 beds
Apr 7 – 12
4.96 out of 5 average rating, 137 reviews
Guest favorite
Home in Becket
Lindal Cedar Berkshires Lake House
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Lee
Studio 208 at Garfield Annex on Main St
1 bed
Apr 1 – 6
4.91 out of 5 average rating, 56 reviews
Superhost
Apartment in Pittsfield
Sharon's Place 5 420 friendly!!!!!!
2 beds
Apr 3 – 10
4.75 out of 5 average rating, 141 reviews
Superhost
Home in Great Barrington
Beautiful House In The Woods, Huge Yard, Hot Tub
5 beds
Apr 1 – 6
4.9 out of 5 average rating, 39 reviews
Guest favorite
Home in Great Barrington
GB at your doorstep
4 beds
Apr 1 – 6
4.94 out of 5 average rating, 89 reviews
Guest favorite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 beds
Apr 1 – 6
4.99 out of 5 average rating, 200 reviews
Superhost
Home in Hancock
Bougie B's Mountainside Getaway
2 beds
Apr 1 – 6
New place to stay
Home in Hillsdale
Modern Luxury Estate w/guesthouse, 45 scenic acres
6 beds
Apr 10 – 15
New place to stay
Superhost
Home in Great Barrington
Classic Berkshires cottage in sun-drenched meadow
7 beds
Apr 1 – 7
4.94 out of 5 average rating, 18 reviews
Guest favorite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 queen beds
Apr 2 – 7
5.0 out of 5 average rating, 26 reviews
Superhost
Home in Lenox
Berkshire, MA Getaway! Mile to town
3 queen beds
Apr 1 – 6
4.86 out of 5 average rating, 328 reviews