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Guest favorite
Home in Pittsfield
Berkshire Lake- Modern and Updated-close to skiing
14 guests5 bedrooms9 beds3.5 baths
May 1 – 6
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May 1 – 6
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ﺩ.ﺇ11,623 for 5 nights
for 5 nights

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Superhost
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
May 4 – 9
ﺩ.ﺇ1,339 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 1 – 6
ﺩ.ﺇ2,410 for 5 nights
for 5 nights
Top guest favorite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
May 2 – 7
ﺩ.ﺇ2,325 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
May 1 – 6
ﺩ.ﺇ2,748 for 5 nights
for 5 nights
4.91 out of 5 average rating, 255 reviews
Top guest favorite
Guest suite in Pittsfield
Private Luxury Apt. Berkshires!
2 beds
May 1 – 6
ﺩ.ﺇ3,443 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 beds
May 1 – 6
ﺩ.ﺇ6,034 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.ﺇ1,938 for 5 nights
for 5 nights
4.86 out of 5 average rating, 7 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Petite space for a getaway
May 1 – 6
ﺩ.ﺇ1,614 for 5 nights
for 5 nights
5.0 out of 5 average rating, 24 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Free cancellation
May 19 – 24
ﺩ.ﺇ1,799 for 5 nights
for 5 nights
4.83 out of 5 average rating, 172 reviews
Top guest favorite
Apartment in Pittsfield
Modern Gem in the Heart of Berkshires
2 beds
May 1 – 6
ﺩ.ﺇ3,014 for 5 nights
for 5 nights
4.93 out of 5 average rating, 41 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
Free cancellation
May 13 – 18
ﺩ.ﺇ2,540 for 5 nights
for 5 nights
4.89 out of 5 average rating, 64 reviews
Top guest favorite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 beds
May 2 – 7
ﺩ.ﺇ7,684 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 5 – 10
ﺩ.ﺇ4,208 for 5 nights
for 5 nights
4.95 out of 5 average rating, 166 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
May 19 – 24
ﺩ.ﺇ1,830 for 5 nights
for 5 nights
4.91 out of 5 average rating, 44 reviews
Bed and breakfast in Pittsfield
Tiny Room & Bath — No Clean Fee!
Free cancellation
May 8 – 13
ﺩ.ﺇ1,163 for 5 nights
for 5 nights
4.58 out of 5 average rating, 59 reviews
Home in Pittsfield
Ohana House
4 beds
May 2 – 7
ﺩ.ﺇ4,821 for 5 nights
for 5 nights
Guest favorite
Apartment in Pittsfield
*Berkshire's Sweet Spot-Close to ski/Spa open
Free cancellation
May 4 – 9
ﺩ.ﺇ6,888 for 5 nights
for 5 nights
4.97 out of 5 average rating, 70 reviews
Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Free cancellation
May 16 – 21
ﺩ.ﺇ2,966 for 5 nights
for 5 nights
5.0 out of 5 average rating, 202 reviews