Pittsfield Vacation Rentals
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Our top choices for Pittsfield vacation 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)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
The price is CA $418
CA $749 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $865
CA $1,589 total
includes taxes & fees
Sep 21 - Sep 22
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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
Varun M.
The price is CA $98
CA $283 total
includes taxes & fees
Sep 20 - Sep 21
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 CA $147
CA $341 total
includes taxes & fees
Sep 20 - Sep 21
5. 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, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
Diego G.
The price is CA $246
CA $745 total
includes taxes & fees
Sep 24 - Sep 25
6. 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 CA $316
CA $707 total
includes taxes & fees
Sep 23 - Sep 24
7. 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 CA $225
CA $760 total
includes taxes & fees
Sep 21 - Sep 22
8. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is CA $81
CA $413 total
includes taxes & fees
Sep 27 - Sep 28
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.
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Top Pittsfield Hotel Reviews
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
10/10 Excellent
Find out more about Pittsfield
Pittsfield Vacation Homes information
Number of reviews | 281 |
|---|---|
Accommodation | 420 Vacation Homes |
Lowest Price | CA $256 |
Highest Price | CA $1,589 |
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