Search Resorts in Pittsfield
Most properties are fully refundable. Because flexibility matters.
Save an average of 15% on thousands of hotels with Expedia Rewards
Search over 2.9 million properties and 550 airlines worldwide
Check availability on Resorts in Pittsfield
Browse Select Pittsfield Resorts
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
10.0 out of 10, Exceptional, (2)
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Save an average of 15% on thousands of hotels when you're signed in
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!
9.8 out of 10, Exceptional, (13)
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
10.0 out of 10, Exceptional, (1)
Vacation Village In The Berkshires 5 Star Resort - Suite B
Vacation Village In The Berkshires 5 Star Resort - Suite B
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
10.0 out of 10, Exceptional, (2)
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
10.0 out of 10, Exceptional, (1)
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Mountain Lodge Apt!
Mountain Lodge Apt!
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort
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 property types in Pittsfield
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very good, (857)
The price is £130
per night
13 May - 14 May
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (182)
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.
Pittsfield Resorts information
Number of reviews | 19 |
---|---|
Accommodation | 12 Resorts |
Lowest Price | |
Highest Price |
Frequently asked questions
Pittsfield Hotel ReviewsExpedia verified reviews
5/5 Excellent
Great place, wonderful location, gracious hosts
"safe, clean, perfect location. Communicative hosts who ensured that someone would be on location when I arrived late. Continental breakfast was extensive and healthy. Will definitely be visiting again. "
A verified traveller stayed at The Lenox Collection
Posted 3 days ago
Top Resorts destinations
More accommodation types in Pittsfield
All Accommodation Types
Be inspired: Top Resorts destinations in 2024
- Orlando Hotel Resorts
- Hotel Resorts in Mexico
- Maldives Hotel Resorts
- Hotel Resorts in Spain
- Hotel Resorts in Turkey
- Hotel Resorts in United Kingdom
- Bali Hotel Resorts
- Cancun Hotel Resorts
- Majorca Island Hotel Resorts
- Hotel Resorts in Canary Islands
- Hotel Resorts in Caribbean
- Hotel Resorts in France
- Hotel Resorts in Italy
- Hotel Resorts in Greece
- Hotel Resorts in Portugal
- Hotel Resorts in Thailand
- Walt Disney World® Resort Hotel Resorts
- Hotel Resorts in Jamaica
- Hotel Resorts in Crete
- Hotel Resorts in Florida