Search Holiday Homes in Pittsfield
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Pittsfield holiday homes
1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
8.4 out of 10, Very good, (10 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
Liz V.
The price is £400
includes taxes & fees
14 Aug - 15 Aug
2. Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
Price F.
The price is £834
includes taxes & fees
9 Sept - 10 Sept
3. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
Joanna P.
The price is £175
includes taxes & fees
16 Aug - 17 Aug
4. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
Leslie H.
The price is £184
includes taxes & fees
9 Sept - 10 Sept
5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
Christine C.
The price is £384
includes taxes & fees
8 Sept - 9 Sept
6. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
Maura L.
The price is £404
includes taxes & fees
13 Aug - 14 Aug
7. stylish Berkshires Retreat
stylish Berkshires RetreatLee
8.8 out of 10, Excellent, (3 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
Donna K.
The price is £322
includes taxes & fees
24 Aug - 25 Aug
8. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.8 out of 10, Exceptional, (6 reviews)
"excellent communication with property manager."
Nancy H.
The price is £410
includes taxes & fees
16 Aug - 17 Aug
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Pittsfield Hotel Reviews
Vacation Village in the Berkshires
8/10 Good
Find out more about Pittsfield
Pittsfield Holiday Homes information
Number of reviews | 204 |
|---|---|
Accommodation | 449 Holiday Homes |
Lowest Price | £155 |
Highest Price | £834 |