Search Pittsfield Cottages
Most properties are fully refundable. Because flexibility matters.
Save 10% or more on over 100,000 hotels worldwide as a One Key member.
Search over 2.9 million properties and 550 airlines worldwide.
Check availability on Cottages in Pittsfield
Compare 79 Cottages in Pittsfield with updated reviews, rates, and availability.
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (32)
Save an average of 15% on thousands of hotels when you're signed in
Cottage in the Berkshires 10 min. to Great Barrington
Cottage in the Berkshires 10 min. to Great Barrington
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
Cozy Cottage in the Woods
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
Spacious Cottage Retreat on Beautiful 2-Acres
Spacious Cottage Retreat on Beautiful 2-Acres
Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
Morgan House on Crooked Lake
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
Caretaker's Cottage: 20 minutes to Tanglewood
Caretaker's Cottage: 20 minutes to Tanglewood
10.0 out of 10, Exceptional, (3)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
Beautiful Berkshires Cottage on Lake Buel
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
Waterfalls and Trails at 'the Mills At Green Hole'
Waterfalls and Trails at 'the Mills At Green Hole'
Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
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 $149
$163 total
includes taxes & fees
May 17 - May 18
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (183)
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 Cottages information
Number of reviews | 262 |
---|---|
Accommodation | 79 Cottages |
Lowest Price | |
Highest Price |
Frequently asked questions
Recent reviews of Pittsfield hotelsExpedia verified reviews
5/5 Excellent
"Lovely room and bar"
A verified traveler stayed at Life House Berkshires
Posted 23 hours ago
Top Cottages in Other Destinations
All Accommodation Types
Be inspired: Top Cottages destinations in 2024
- Sanibel Cottages
- Cottages in Michigan
- Cottage Grove Cottages
- Key West Cottages
- Cottages in Florida
- Destin Cottages
- Cottages in Maine
- Tybee Island Cottages
- Myrtle Beach Cottages
- Cottages in Ontario
- Cottages in France
- Lake George Cottages
- Asheville Cottages
- Bar Harbor Cottages
- Geneva-on-the-Lake Cottages
- Siesta Key Cottages
- Prince Edward Island Cottages
- Fredericksburg Cottages
- Cottages in United Kingdom
- Eureka Springs Cottages
Most searched themes and destinations in 2024
- Beach Hotels in Oceanside
- Beach Hotels in Ocean City
- Beach Hotels in Myrtle Beach
- Beach Hotels in Ocean Shores
- Beach Hotels in Ocean Isle Beach
- Beach Hotels in Miami
- Beach Hotels in Virginia Beach
- Beach Hotels in San Diego
- Beach Hotels in Ocean Springs
- Beach Hotels in Key West
- Beach Hotels in Orlando
- Beach Hotels in Destin
- Beach Hotels in Los Angeles
- Beach Hotels in Charleston
- Beach Hotels in Daytona Beach
- Beach Hotels in Panama City Beach
- Beach Hotels in North Myrtle Beach
- Beach Hotels in Tampa
- Beach Hotels in Fort Lauderdale
- Beach Hotels in St Augustine
Expedia's Latest Trends
Hotels
Hotels in SturbridgeHotels in AmherstHotels in SpringfieldHotels in ChathamHotels in Fall RiverHotels in HyannisHotels in ProvincetownHotels in PlymouthHotels in NewburyportHotels in FoxboroHotels in LowellHotels in NantucketHotels in RockportHotels in NorthamptonHotels in FalmouthCheap Hotels in BrocktonHotels in MansfieldCheap Hotels in SpringfieldHotels in WorcesterHotels in MarlboroughHotels in GloucesterHotels in New BedfordCheap Hotels in Worcester
Flights
Cars
Activities