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Guest favorite
Home in Pittsfield
Berkshire Lake- Modern and Updated-close to skiing
14 guests5 bedrooms9 beds3.5 baths
May 3 – 8
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May 3 – 8
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ﺩ.ﺇ 11,623 for 5 nights
for 5 nights

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Top guest favorite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
May 4 – 9
ﺩ.ﺇ 2,325 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Superhost
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
May 5 – 10
ﺩ.ﺇ 1,334 for 5 nights
for 5 nights
4.9 out of 5 average rating, 59 reviews
Apartment in Pittsfield
Spacious 2 bedroom downtown
3 beds
May 3 – 8
ﺩ.ﺇ 2,410 for 5 nights
for 5 nights
4.67 out of 5 average rating, 3 reviews
Top guest favorite
Guest suite in Pittsfield
Private Luxury Apt. Berkshires!
2 beds
May 3 – 8
ﺩ.ﺇ 3,408 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
May 3 – 8
ﺩ.ﺇ 2,987 for 5 nights
for 5 nights
4.91 out of 5 average rating, 255 reviews
Guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 beds
May 3 – 8
ﺩ.ﺇ 6,034 for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
Guest favorite
Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
May 12 – 17
ﺩ.ﺇ 1,938 for 5 nights
for 5 nights
4.86 out of 5 average rating, 7 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
Free cancellation
May 13 – 18
ﺩ.ﺇ 2,540 for 5 nights
for 5 nights
4.89 out of 5 average rating, 64 reviews
Top guest favorite
Apartment in Pittsfield
Modern Gem in the Heart of Berkshires
2 beds
May 3 – 8
ﺩ.ﺇ 3,014 for 5 nights
for 5 nights
4.93 out of 5 average rating, 41 reviews
Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Free cancellation
May 16 – 21
ﺩ.ﺇ 2,966 for 5 nights
for 5 nights
5.0 out of 5 average rating, 202 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
May 19 – 24
ﺩ.ﺇ 1,830 for 5 nights
for 5 nights
4.91 out of 5 average rating, 44 reviews
Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 beds
May 4 – 9
ﺩ.ﺇ 7,426 for 5 nights
for 5 nights
4.98 out of 5 average rating, 58 reviews
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
May 26 – 31
ﺩ.ﺇ 4,340 for 5 nights
for 5 nights
4.95 out of 5 average rating, 167 reviews
Bed and breakfast in Pittsfield
Tiny Room & Bath — No Clean Fee!
1 bed
May 3 – 8
ﺩ.ﺇ 1,163 for 5 nights
for 5 nights
4.58 out of 5 average rating, 59 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Petite space for a getaway
May 8 – 13
ﺩ.ﺇ 1,743 for 5 nights
for 5 nights
5.0 out of 5 average rating, 25 reviews
Bed and breakfast in Pittsfield
Room #5 with Queen size bed
1 queen bed
May 3 – 8
ﺩ.ﺇ 1,679 for 5 nights
for 5 nights
4.41 out of 5 average rating, 17 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
May 4 – 9
ﺩ.ﺇ 1,743 for 5 nights
for 5 nights
4.98 out of 5 average rating, 410 reviews
Guest favorite
Apartment in Pittsfield
*Berkshire's Sweet Spot-Close to ski/Spa open
4 beds
May 4 – 9
ﺩ.ﺇ 6,888 for 5 nights
for 5 nights
4.97 out of 5 average rating, 70 reviews