Search results; Over 1,000 places

Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
10 min drive
Aug 3 – 8
R15,337 ZAR for 5 nights, originally R18,908 ZAR
4.99 out of 5 average rating, 231 reviews
Guest favorite
Home in Pittsfield
Dancing Horse Lodge
10 min drive
Aug 31 – Sep 5
R16,745 ZAR for 5 nights
4.87 out of 5 average rating, 293 reviews
Top guest favorite
Room in Pittsfield
Petite space for a getaway
20 min drive
Jul 27 – Aug 1
R10,133 ZAR for 5 nights
5.0 out of 5 average rating, 37 reviews
Top guest favorite
Cottage in Pittsfield
Cozy Berkshire cottage with indoor fireplace
10 min drive
Sep 14 – 19
R28,050 ZAR for 5 nights
5.0 out of 5 average rating, 102 reviews
Room in Pittsfield
Room with Queen size bed
20 min drive
Jul 14 – 19
R6,400 ZAR for 5 nights
4.57 out of 5 average rating, 23 reviews
Top guest favorite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
20 min drive
Aug 10 – 15
R11,199 ZAR for 5 nights
4.98 out of 5 average rating, 422 reviews
Superhost
Room in Pittsfield
The Yellow Room
20 min drive
Aug 12 – 17
R7,765 ZAR for 5 nights
4.87 out of 5 average rating, 68 reviews
Top guest favorite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
10 min drive
Jul 20 – 25
R12,052 ZAR for 5 nights
5.0 out of 5 average rating, 59 reviews
Top guest favorite
Room in Pittsfield
Airy Queen Bedroom with Couch, Pittsfield
20 min drive
Jul 19 – 24
R14,896 ZAR for 5 nights
4.95 out of 5 average rating, 66 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
10 min drive
Jul 20 – 25
R16,493 ZAR for 5 nights
4.91 out of 5 average rating, 268 reviews
Room in Pittsfield
Charming Turret Room in Downtown Victorian
10 min drive
Aug 4 – 9
R7,999 ZAR for 5 nights
4.67 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Pittsfield
Green 2 bedroom Downtown
10 min drive
Jul 27 – Aug 1
R14,292 ZAR for 5 nights
4.92 out of 5 average rating, 25 reviews
Superhost
Apartment in Pittsfield
Newly Renovated, and Spacious great for family
20 min drive
Sep 7 – 12
R7,752 ZAR for 5 nights
4.82 out of 5 average rating, 50 reviews
Top guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
10 min drive
Jul 27 – Aug 1
R20,819 ZAR for 5 nights
4.96 out of 5 average rating, 82 reviews
Guest favorite
Room in Pittsfield
Modern, Spacious Master Bedroom and Bathroom
10 min drive
Jul 21 – 26
R16,532 ZAR for 5 nights
4.92 out of 5 average rating, 86 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
20 min drive
Jul 28 – Aug 2
R12,052 ZAR for 5 nights
4.89 out of 5 average rating, 76 reviews
Home in Pittsfield
Beautiful & Serene Getaway
10 min drive
Aug 3 – 8
R25,394 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Pittsfield
Spacious 2 bedroom downtown
10 min drive
Aug 3 – 8
R14,612 ZAR for 5 nights
4.86 out of 5 average rating, 14 reviews