Search Vacation Homes in Pittsfield
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Vacation Homes in Pittsfield
Compare 343 Vacation Homes in Pittsfield with updated reviews, rates, and availability.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Pittsfield
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1713)
The price is SAR 633
SAR 732 total
includes taxes & fees
23 Sep - 24 Sep
The price is SAR 559
SAR 613 total
includes taxes & fees
14 Oct - 15 Oct
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels
5/5 Excellent
"The breakfast is mediocre-- coffee cold my first day (OK the second). No cereal except granola. Congested area."
A verified traveler stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Pittsfield
- Apartments in Pittsfield (93)
- Cottages in Pittsfield (80)
- Cabin Rentals in Pittsfield (41)
- Condo Rentals in Pittsfield (39)
- B&B in Pittsfield (30)
- Motels in Pittsfield (30)
- Resorts in Pittsfield (26)
- Farmstay in Pittsfield (20)
- Aparthotels in Pittsfield (8)
- Guest Houses in Pittsfield (6)
- Chalets in Pittsfield (5)
- Inns in Pittsfield (5)
- Villas in Pittsfield (3)
- Condo Resorts in Pittsfield (2)
- Lodges in Pittsfield (2)
- Hotels (1,256)