Search results; Over 1,000 homes in Pittsfield

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Guest favorite
Private room in Pittsfield
Petite space for a getaway
2 guests1 bedroom1 bed1 private bath
May 1 – 6
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May 1 – 6
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ﺩ.ﺇ1,744 for 5 nights

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Superhost
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
Sep 8 – 13
ﺩ.ﺇ1,335 for 5 nights
4.85 out of 5 average rating, 72 reviews
Superhost
Apartment in Pittsfield
Newly Renovated, and Spacious great for family
1 queen bed
Sep 7 – 12
ﺩ.ﺇ1,433 for 5 nights
4.73 out of 5 average rating, 60 reviews
Top guest favorite
Home in Pittsfield
Marie’s Place unit 3
3 beds
Sep 6 – 11
ﺩ.ﺇ4,395 for 5 nights
4.98 out of 5 average rating, 42 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
Sep 8 – 13
ﺩ.ﺇ1,830 for 5 nights
4.91 out of 5 average rating, 47 reviews
Apartment in Pittsfield
Beautiful Blue Studio downtown
1 bed
Sep 7 – 12
ﺩ.ﺇ1,436 for 5 nights
4.59 out of 5 average rating, 37 reviews
Room in Pittsfield
Stay with Julia
No Clean Fee! Upper North St Lodge Room
Sep 1 – 6
ﺩ.ﺇ1,337 for 5 nights
4.69 out of 5 average rating, 91 reviews
Superhost
Apartment in Pittsfield
Charming Apartment In The Heart of The Berkshires
1 queen bed
Sep 2 – 7
ﺩ.ﺇ3,500 for 5 nights
Guest favorite
Apartment in Lenox
Station House 1E Private Room & Bath
1 bed
Sep 15 – 20
ﺩ.ﺇ1,722 for 5 nights
4.88 out of 5 average rating, 195 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
May 1 – 6
ﺩ.ﺇ2,351 for 5 nights
4.98 out of 5 average rating, 430 reviews
Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 beds
Sep 4 – 9
ﺩ.ﺇ7,685 for 5 nights
4.98 out of 5 average rating, 60 reviews
Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
Sep 9 – 14
ﺩ.ﺇ1,981 for 5 nights
4.67 out of 5 average rating, 15 reviews
Guest favorite
Room in Dalton
Stay with DanielHosting for 6 years,
Appalachian Trail Getaway
Sep 8 – 13
ﺩ.ﺇ1,572 for 5 nights
4.81 out of 5 average rating, 62 reviews
Top guest favorite
Home in Pittsfield
Spacious Farmhouse with Stunning Views
5 beds
Sep 6 – 11
ﺩ.ﺇ8,826 for 5 nights
5.0 out of 5 average rating, 13 reviews
Top guest favorite
Guest suite in Pittsfield
Private Luxury Apt. Berkshires!
2 beds
Sep 8 – 13
ﺩ.ﺇ4,800 for 5 nights
5.0 out of 5 average rating, 19 reviews
Superhost
Room in Pittsfield
Stay with Berkshire Theatre Group
The Artist House - Room 5
Nov 1 – 6
ﺩ.ﺇ2,067 for 5 nights
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
6 beds
Sep 2 – 7
ﺩ.ﺇ10,655 for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Sep 6 – 11
ﺩ.ﺇ2,891 for 5 nights
4.92 out of 5 average rating, 274 reviews
Top guest favorite
Home in Pittsfield
BB's Central Berkshire Home
5 beds
Sep 1 – 6
ﺩ.ﺇ4,615 for 5 nights
4.95 out of 5 average rating, 79 reviews