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Guest favorite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
4 guests2 bedrooms2 beds1 bath
Aug 26 – 31
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Aug 26 – 31
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R41,162 ZAR for 5 nights

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Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
Aug 4 – 9
R7,928 ZAR for 5 nights
4.64 out of 5 average rating, 11 reviews
Superhost
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
Aug 12 – 17
R7,738 ZAR for 5 nights
4.87 out of 5 average rating, 68 reviews
Superhost
Apartment in Pittsfield
Spacious 2 bedroom downtown
3 beds
Jul 13 – 18
R13,425 ZAR for 5 nights
4.86 out of 5 average rating, 14 reviews
Superhost
Apartment in Pittsfield
Newly Renovated, and Spacious great for family
Free cancellation
Sep 7 – 12
R8,436 ZAR for 5 nights
4.82 out of 5 average rating, 50 reviews
Guest favorite
Apartment in Pittsfield
Green 2 bedroom Downtown
3 beds
Jul 27 – Aug 1
R12,685 ZAR for 5 nights
4.92 out of 5 average rating, 25 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
Free cancellation
Jul 28 – Aug 2
R11,945 ZAR for 5 nights
4.89 out of 5 average rating, 75 reviews
Bed and breakfast in Pittsfield
Tiny Room & Bath — No Clean Fee!
Free cancellation
Aug 23 – 28
R5,709 ZAR for 5 nights
4.58 out of 5 average rating, 59 reviews
Room in Pittsfield
Stay with Alejandro
Room with Queen size bed
Jul 13 – 18
R6,766 ZAR for 5 nights
4.57 out of 5 average rating, 23 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Petite space for a getaway
Jul 27 – Aug 1
R10,042 ZAR for 5 nights
5.0 out of 5 average rating, 36 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
Free cancellation
Sep 1 – 8
R10,566 ZAR for 7 nights
4.91 out of 5 average rating, 47 reviews
Top guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
Free cancellation
Aug 25 – 30
R37,314 ZAR for 5 nights
5.0 out of 5 average rating, 18 reviews
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Aug 3 – 8
R21,408 ZAR for 5 nights
4.95 out of 5 average rating, 176 reviews
Top guest favorite
Room in Pittsfield
Stay with EileenHosting for 4 years,
2-Rm Suite in the Berkshires - private BR and Den
Sep 7 – 12
R11,945 ZAR for 5 nights
5.0 out of 5 average rating, 57 reviews
Top guest favorite
Room in Pittsfield
Stay with LynetteHigher education, pr,
Airy Queen Bedroom with Couch, Pittsfield
Jul 10 – 15
R14,763 ZAR for 5 nights
4.95 out of 5 average rating, 66 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Jul 20 – 25
R16,347 ZAR for 5 nights
4.91 out of 5 average rating, 267 reviews
Apartment in Pittsfield
Beautiful Blue Studio downtown
1 bed
Jul 13 – 18
R10,888 ZAR for 5 nights
4.55 out of 5 average rating, 33 reviews
Guest favorite
Room in Pittsfield
Stay with Rachel
Sunny Room in Downtown Victorian
Oct 1 – 6
R8,880 ZAR for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Room in Dalton
Stay with MaryHosting for 6 years,
Mother in Law unit in Dalton
Aug 10 – 15
R11,353 ZAR for 5 nights
4.95 out of 5 average rating, 152 reviews