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Search results; 350 rooms in Pittsfield

Guest favorite
Room in Becket
Stay with Robb And JuliaSelf-employed,
East b.r. in upstairs suite of open plan home
Apr 1 – 6
4.85 out of 5 average rating, 192 reviews
Superhost
Room in Stephentown
Stay with ThomasReal estate,
A Stay at the Homestead 3
Apr 1 – 6
4.9 out of 5 average rating, 10 reviews
Guest favorite
Room in Ashfield
Stay with AmyEducation,
Private room and bath in sunny large home.
Apr 1 – 6
4.99 out of 5 average rating, 93 reviews
Room in Pittsfield
Stay with CarolynAcupuncture, author,
Duchess of Pomeroy Penthouse
Apr 9 – 14
Guest favorite
Room in Richmond
Stay with KarenHosting for 5 years,
BLUE HEAVEN FARM; A BERKSHIRE EXPERIENCE
Apr 1 – 6
4.71 out of 5 average rating, 48 reviews
Room in Pittsfield
Stay with AccemHosting for 9 years,
Accem’s Dream House
Apr 1 – 6
5.0 out of 5 average rating, 4 reviews
Superhost
Room in Pittsfield
Stay with PaulHosting for 10 years,
Great location, private entrance w/shared bath
Apr 1 – 6
4.82 out of 5 average rating, 11 reviews
Guest favorite
Room in Philmont
Stay with TeshnaHosting for 9 years,
Lovely Quiet Private Room
Apr 1 – 6
5.0 out of 5 average rating, 6 reviews
Guest favorite
Room in Becket
Stay with Robb And JuliaSelf-employed,
priv. rm.#2 in forest clearing home
Apr 1 – 6
4.79 out of 5 average rating, 288 reviews
Room in Pittsfield
Stay with CarolynAcupuncture, author,
Duchess of Pomeroy Master Bedroom
Apr 9 – 14
Guest favorite
Room in Bennington
Stay with LeslieHosting for 5 years,
Leslie’s Bright & Cozy: King Room
Apr 1 – 6
4.99 out of 5 average rating, 85 reviews
Guest favorite
Room in Becket
Stay with DonnaNurse,
Farmhouse Suite on Berkshire Farm
May 3 – 8
4.94 out of 5 average rating, 141 reviews
Guest favorite
Room in Bennington
Stay with LeslieHosting for 5 years,
Leslie’s Bright & Cozy: Queen Room
Apr 1 – 6
4.95 out of 5 average rating, 82 reviews
Guest favorite
Room in Pittsfield
Stay with CateHosting for 4 years,
Coming soon: Annex at Cottage Oasis
Jun 14 – 19
4.92 out of 5 average rating, 38 reviews
Superhost
Room in East Chatham
Stay with Chloe
The Inn at Silver Maple Farm - Upper Lodge
Apr 6 – 11
5.0 out of 5 average rating, 3 reviews
Guest favorite
Room in Huntington
Stay with SandraHosting for 7 years,
Antique colonial
Apr 18 – 23
4.87 out of 5 average rating, 162 reviews
Guest favorite
Room in Lanesborough
Stay with Carlton
1bed rm. skier’s bliss 2 miles only 1 rd to slopes
May 1 – 6
4.87 out of 5 average rating, 52 reviews
Room in Rensselaer
Stay with Jorge
Own room in private home.
Apr 1 – 6
New place to stay