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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
8.6 out of 10, Excellent, (11 reviews)
The price is AED 988
AED 1,736 total
includes taxes & fees
15 Nov - 16 Nov

2. Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (22 reviews)
The price is AED 2,310
AED 4,007 total
includes taxes & fees
17 Nov - 18 Nov

3. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
The price is AED 312
AED 766 total
includes taxes & fees
15 Nov - 16 Nov

4. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
The price is AED 257
AED 711 total
includes taxes & fees
16 Nov - 17 Nov

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (6 reviews)
The price is AED 599
AED 1,498 total
includes taxes & fees
16 Nov - 17 Nov

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
The price is AED 746
AED 2,104 total
includes taxes & fees
15 Nov - 16 Nov

7. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
The price is AED 1,167
AED 2,218 total
includes taxes & fees
15 Nov - 16 Nov

8. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is AED 224
AED 1,042 total
includes taxes & fees
26 Nov - 27 Nov

9. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
The price is AED 1,183
AED 2,428 total
includes taxes & fees
15 Nov - 16 Nov

11. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is AED 1,253
AED 2,187 total
includes taxes & fees
16 Nov - 17 Nov

12. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
The price is AED 536
AED 1,320 total
includes taxes & fees
16 Nov - 17 Nov

13. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is AED 588
AED 1,326 total
includes taxes & fees
16 Nov - 17 Nov

14. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
The price is AED 646
AED 1,120 total
includes taxes & fees
15 Nov - 16 Nov

15. NEW RENO Historic Creamery in Berkshires w/hot tub
NEW RENO Historic Creamery in Berkshires w/hot tubNew Lebanon
10.0 out of 10, Exceptional, (8 reviews)
The price is AED 1,054
AED 2,043 total
includes taxes & fees
9 Dec - 10 Dec

16. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is AED 744
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov

17. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)

18. Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Walk to Williams * Steam Sauna * Ritz-Carlton BedWilliamstown
10.0 out of 10, Exceptional, (2 reviews)

19. Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Walk into town, soak up sun on enclosed porch & steps away from nature trails!Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
The price is AED 1,690
AED 3,028 total
includes taxes & fees
7 Dec - 8 Dec

20. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is AED 735
AED 1,112 total
includes taxes & fees
13 Dec - 14 Dec
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.
Learn more about Pittsfield
Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.







































































































































