Pittsfield Vacation Rentals
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Vacation Rentals in Pittsfield
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (858)
The price is ¥24,501
¥26,878 total
includes taxes & fees
Jun 3 - Jun 4
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Save an average of 15% on thousands of hotels when you're signed in
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (117)
Serene Acreage - Pond - Hiking Trails Nearby
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
Bear Creek Cabin
Bear Creek Cabin
10.0 out of 10, Exceptional, (14)
The price is ¥62,768
¥94,653 total
includes taxes & fees
Jun 3 - Jun 4
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
3 Bedroom Lakefront Home with Hot Tub & Fireplace
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (97)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (205)
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
Quintessential 6-BR Berkshires Lodge
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, (79)
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.
Other types of properties in Pittsfield you may be interested in
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
7.8 out of 10, Good, (581)
The price is ¥20,597
¥23,006 total
includes taxes & fees
Jun 10 - Jun 11
Berkshire Mountain Lodge
Berkshire Mountain Lodge
8.8 out of 10, Excellent, (312)
The price is ¥25,892
¥32,060 total
includes taxes & fees
Jun 3 - Jun 4
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
8.4 out of 10, Very Good, (948)
The price is ¥19,497
¥21,778 total
includes taxes & fees
May 30 - May 31
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.
Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:
- View our selection of featured holiday rentals in Pittsfield
- Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last
Look no further and take a look at our great range of rental properties in Pittsfield!
Frequently asked questions
Recent reviews of Pittsfield propertiesExpedia verified reviews
5/5 Excellent
"We had a warm welcome when we got to the hotel. Any questions we had, they had the right information. Everything thing was clean and up to date. I love the fact that though out the lobby and the rooms they had local artists and students artwork. "
A verified traveler stayed at Hotel Downstreet
Posted 1 day ago