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Search results; Over 1,000 places

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Guest favourite
Flat in Pittsfield
The sweet place in the beautiful Berkshires!
6-min drive
7–12 FebHosted by Teresa,
4.96 out of 5 average rating, 47 reviews
Superhost
Room in Pittsfield
Room with a Twin size bed #3
3-min drive
1–6 AprHosted by Alejandro,
4.85 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Pittsfield
Adorable lakeside cottage on a quiet cove!
1-min walk
31 Oct – 5 NovHosted by Mackenzie,
5.0 out of 5 average rating, 28 reviews
Guest favourite
Cottage in Lanesborough
Amazing 2 bedroom lake front cottage, large patio
6-min drive
3–8 MayHosted by Lynne,
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
8-min drive
7–12 AprHosted by Jia,
4.94 out of 5 average rating, 98 reviews
Guest favourite
Home in Lanesborough
Lake Views, Lrg Open Grand Room+Kitchen, Hot Tub
5-min drive
8–13 AprHosted by Kristine,
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Pittsfield
BB's Central Berkshire Home
13-min drive
1–6 AprHosted by JoAnn & Kate,
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
9-min walk
7–12 AprHosted by Margaret,
4.83 out of 5 average rating, 161 reviews
Superhost
Home in Hancock
Bougie B's Mountainside Getaway
19-min drive
1–6 AprHosted by Jaryn,
New place to stay
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
9-min drive
5–10 AprHosted by Paul,
4.87 out of 5 average rating, 246 reviews
Guest favourite
Flat in Pittsfield
Comfortable Pittsfield Loft
6-min drive
1–6 AprHosted by Michael,
4.92 out of 5 average rating, 24 reviews
Flat in Pittsfield
Beautiful Blue Studio downtown
5-min drive
1–6 AprHosted by Nubia,
New place to stay
Guest favourite
Cottage in Pittsfield
Cozy Berkshire cottage with indoor fireplace
8-min drive
1–6 AprHosted by Sarah,
5.0 out of 5 average rating, 81 reviews
Guest favourite
Home in Lebanon Springs
Summer Getaway: Historic Home Near Tanglewood
16-min drive
7–12 AprHosted by Amanda,
4.92 out of 5 average rating, 71 reviews
Guest favourite
Room in Pittsfield
Room with Queen size bed #1
3-min drive
1–6 AprHosted by Alejandro,
4.92 out of 5 average rating, 12 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
3-min drive
7–12 AprHosted by Marie,
4.91 out of 5 average rating, 223 reviews
Guest favourite
Apartment in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
19-min drive
5–10 AprHosted by Renee,
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Lanesborough
Scenic mountain getaway.
15-min drive
9–14 AprHosted by Sandra,
5.0 out of 5 average rating, 46 reviews