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Apartments
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
8.6 out of 10, Excellent, (11 reviews)
The price is £352
includes taxes & fees
12 Nov - 13 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 £777
includes taxes & fees
1 Dec - 2 Dec

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 £162
includes taxes & fees
12 Nov - 13 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 £151
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, (5 reviews)
The price is £307
includes taxes & fees
18 Nov - 19 Nov

6. 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 £382
includes taxes & fees
12 Nov - 13 Nov

7. 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 £420
includes taxes & fees
12 Nov - 13 Nov

8. 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 £431
includes taxes & fees
13 Nov - 14 Nov

9. 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 £217
includes taxes & fees
16 Nov - 17 Nov

10. 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 £462
includes taxes & fees
16 Nov - 17 Nov

11. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (15 reviews)
The price is £148
includes taxes & fees
23 Nov - 24 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 £268
includes taxes & fees
15 Nov - 16 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 £272
includes taxes & fees
12 Nov - 13 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 £222
includes taxes & fees
12 Nov - 13 Nov

15. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is £215
includes taxes & fees
13 Nov - 14 Nov

16. 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 £409
includes taxes & fees
9 Dec - 10 Dec

17. Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Walk to Williams * Steam Sauna * Ritz-Carlton BedWilliamstown
10.0 out of 10, Exceptional, (2 reviews)
The price is £405
includes taxes & fees
29 Nov - 30 Nov

18. 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 £613
includes taxes & fees
1 Dec - 2 Dec

19. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is £962
includes taxes & fees
17 Nov - 18 Nov

20. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
The price is £428
includes taxes & fees
16 Nov - 17 Nov
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.

Top reviews in Pittsfield

Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
















































































































