Search results; Over 1,000 places

Prices include all fees
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
10 min drive
Jun 22 – 27
ﺩ.ﺇ2,605 for 5 nights
for 5 nights
4.91 out of 5 average rating, 325 reviews
Top guest favorite
Home in Mount Washington
Beautiful Berkshires Colonial on 7 Acres
10 min drive
May 18 – 23
ﺩ.ﺇ8,093 for 5 nights
for 5 nights
5.0 out of 5 average rating, 45 reviews
Guest favorite
Cottage in Copake Falls
Beautiful cottage at the foot of the Birkshires
10 min drive
May 26 – 31
ﺩ.ﺇ3,632 for 5 nights
for 5 nights
4.91 out of 5 average rating, 353 reviews
Top guest favorite
Room in Hillsdale
Historic Victorian - Berkshires, Hudson, Catamount
20 min drive
May 18 – 23
ﺩ.ﺇ2,497 for 5 nights
for 5 nights
4.94 out of 5 average rating, 314 reviews
Top guest favorite
Guesthouse in Sheffield
Black Bear Bungalow, Sheffield Mass. U Will Love!
30 min drive
May 19 – 24
ﺩ.ﺇ2,927 for 5 nights, originally ﺩ.ﺇ3,423
for 5 nights
5.0 out of 5 average rating, 14 reviews
Top guest favorite
Farm stay in Ancram
Relaxing secluded stay with loving social animals.
30 min drive
Jun 2 – 7
ﺩ.ﺇ3,943 for 5 nights
for 5 nights
4.96 out of 5 average rating, 325 reviews
Superhost
Cabin in Copake Lake
Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS
20 min drive
May 19 – 24
ﺩ.ﺇ3,926 for 5 nights, originally ﺩ.ﺇ4,321
for 5 nights
4.93 out of 5 average rating, 230 reviews
Guest suite in Salisbury
Bright & Airy Guest Suite
40 min drive
May 19 – 24
ﺩ.ﺇ3,767 for 5 nights
for 5 nights
New place to stay
Guest favorite
Home in Copake
Yellow Door House
20 min drive
May 27 – Jun 1
ﺩ.ﺇ2,841 for 5 nights
for 5 nights
4.92 out of 5 average rating, 62 reviews
Apartment in Hillsdale
Brooks Motel: Chic Renovations, Book Now!
20 min drive
May 17 – 22
ﺩ.ﺇ1,557 for 5 nights, originally ﺩ.ﺇ2,410
for 5 nights
4.58 out of 5 average rating, 103 reviews
Top guest favorite
Apartment in Hillsdale
Serene Suite by Catamount, Hudson, Tanglewood
20 min drive
May 31 – Jun 5
ﺩ.ﺇ2,880 for 5 nights
for 5 nights
4.99 out of 5 average rating, 203 reviews
Guest favorite
Home in Great Barrington
Valley Vista atop Jug End
20 min drive
May 25 – 30
ﺩ.ﺇ6,991 for 5 nights, originally ﺩ.ﺇ8,170
for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
40 min drive
Jun 9 – 14
ﺩ.ﺇ3,568 for 5 nights
for 5 nights
5.0 out of 5 average rating, 359 reviews
Guest favorite
Apartment in Great Barrington
Kitchenette|King Bed|Couch
30 min drive
May 17 – 22
ﺩ.ﺇ2,023 for 5 nights, originally ﺩ.ﺇ4,028
for 5 nights
4.88 out of 5 average rating, 103 reviews
Guest favorite
Cabin in Ancram
As seen in The Guardian, forested hempcabin
30 min drive
Jun 16 – 21
ﺩ.ﺇ5,252 for 5 nights
for 5 nights
4.97 out of 5 average rating, 29 reviews
Home in Copake
Berkshire Mountain Retreat
10 min drive
May 19 – 24
ﺩ.ﺇ2,582 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Home in Copake
Modern Rustic Getaway | Quiet | Wifi |Parking
20 min drive
May 18 – 23
ﺩ.ﺇ5,622 for 5 nights
for 5 nights
4.97 out of 5 average rating, 35 reviews
Guest favorite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
40 min drive
Sep 3 – 8
ﺩ.ﺇ4,668 for 5 nights, originally ﺩ.ﺇ5,208
for 5 nights
4.93 out of 5 average rating, 148 reviews