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Guest favorite
Home in Pittsfield
Berkshire Lake- Modern and Updated-close to skiing
14 guests5 bedrooms9 beds3.5 baths
Jun 15 – 20
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Jun 15 – 20
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ﺩ.ﺇ13,777 for 5 nights
for 5 nights

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Superhost
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
May 26 – 31
ﺩ.ﺇ1,334 for 5 nights
for 5 nights
4.9 out of 5 average rating, 60 reviews
Guest favorite
Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
May 26 – 31
ﺩ.ﺇ1,615 for 5 nights
for 5 nights
4.75 out of 5 average rating, 8 reviews
Guest favorite
Apartment in Pittsfield
Green 2 bedroom Downtown
3 beds
May 26 – 31
ﺩ.ﺇ2,497 for 5 nights
for 5 nights
4.89 out of 5 average rating, 19 reviews
Top guest favorite
Guest suite in Pittsfield
Private Luxury Apt. Berkshires!
Free cancellation
May 27 – Jun 1
ﺩ.ﺇ3,714 for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Jun 1 – 6
ﺩ.ﺇ2,716 for 5 nights
for 5 nights
4.91 out of 5 average rating, 257 reviews
Top guest favorite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
May 26 – 31
ﺩ.ﺇ2,347 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Top guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
Free cancellation
Jun 1 – 6
ﺩ.ﺇ7,289 for 5 nights
for 5 nights
5.0 out of 5 average rating, 13 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Petite space for a getaway
May 25 – 30
ﺩ.ﺇ1,743 for 5 nights
for 5 nights
5.0 out of 5 average rating, 27 reviews
Top guest favorite
Apartment in Pittsfield
Modern Gem in the Heart of Berkshires
Free cancellation
Jul 29 – Aug 3
ﺩ.ﺇ3,272 for 5 nights
for 5 nights
4.93 out of 5 average rating, 44 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
Free cancellation
Aug 17 – 22
ﺩ.ﺇ2,325 for 5 nights
for 5 nights
4.89 out of 5 average rating, 64 reviews
Apartment in Pittsfield
Spacious 2 bedroom downtown
3 beds
May 26 – 31
ﺩ.ﺇ2,410 for 5 nights
for 5 nights
4.75 out of 5 average rating, 4 reviews
Top guest favorite
Home in Pittsfield
Spacious Farmhouse with Stunning Views
Free cancellation
May 27 – Jun 1
ﺩ.ﺇ7,641 for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
Free cancellation
Sep 8 – 13
ﺩ.ﺇ3,228 for 5 nights
for 5 nights
4.93 out of 5 average rating, 100 reviews
Top guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Jun 2 – 7
ﺩ.ﺇ4,212 for 5 nights
for 5 nights
4.95 out of 5 average rating, 171 reviews
Guest favorite
Apartment in Pittsfield
*Berkshire's Sweet Spot-Close to ski/Spa open
Free cancellation
May 26 – 31
ﺩ.ﺇ6,888 for 5 nights
for 5 nights
4.97 out of 5 average rating, 70 reviews
Room in Pittsfield
Stay with Julia
No Clean Fee! Upper North St Lodge Room
Jun 1 – 6
ﺩ.ﺇ1,336 for 5 nights
for 5 nights
4.68 out of 5 average rating, 84 reviews
Top guest favorite
Home in Lanesborough
The Pond House
Free cancellation
May 28 – Jun 2
ﺩ.ﺇ4,658 for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Superhost
Vacation home in Pittsfield
Explore the Berkshires from this charming home.
4 beds
May 28 – Jun 2
ﺩ.ﺇ4,219 for 5 nights
for 5 nights
4.83 out of 5 average rating, 23 reviews