Search Vacation Homes in Pittsfield
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Pittsfield vacation homes
Vacation Home in Pittsfield
3-bedroom house in beautiful Berkshires, close to amenities!$285 nightly
The price is $318
Jan 13 - Jan 14, 2026
Total with taxes and fees
Vacation Home in Pittsfield
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
$442 nightly
The price is $494
Jan 3 - Jan 4, 2026
Total with taxes and fees
Vacation Home in Hancock
Hancock Village Inn Near Jiminy Peak10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
Price F.
$971 nightly
The price is $1,050
Jan 6 - Jan 7, 2026
Total with taxes and fees
Vacation Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
$351 nightly
The price is $392
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Florida
Florida Mountain Log Cabin10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
$340 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Lebanon Springs
Historic Berkshires Home Near Tanglewood, Trails & Wineries8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
Kaye S.
$332 nightly
The price is $372
Jan 8 - Jan 9, 2026
Total with taxes and fees
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.
Top Pittsfield Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about Pittsfield
Pittsfield Vacation Homes information
Number of reviews | 146 |
|---|---|
Accommodation | 417 Vacation Homes |
Lowest Price | $257 |
Highest Price | $1,050 |
Explore a world of travel with Expedia
- Cabin Rentals in Berkshire County
- Hotels near Berkshire Museum
- Hotels near Berkshire Athenaeum
- Hotels near Colonial Theater
- Hotels near Barrington Stage Company
- Hotels near Crane Museum of Papermaking
- Hotels near Pittsfield Station
- Hotels near Canoe Meadows Wildlife Sanctuary
- Hotels near Herman Melville's Arrowhead
- Hotels near Pittsfield Municipal
- Flights to Berkshire County
- Flights from Pittsfield Municipal
- Flights from Albany (ALB) to Pittsfield (PSF)
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights from New York (NYC) to Pittsfield (PSF)
- Flights from Worcester (ORH) to Pittsfield (PSF)
- Flights from Pittsburgh (PIT) to Pittsfield (PSF)
- Flights from Philadelphia (PHL) to Pittsfield (PSF)
- Flights from Charlotte (CLT) to Pittsfield (PSF)
- Flights from Orlando (MCO) to Pittsfield (PSF)
- Flights from Dallas (DFW) to Pittsfield (PSF)
- Flights from Fort Lauderdale (FLL) to Pittsfield (PSF)
- Flights from New York (JFK) to Pittsfield (PSF)
- Flights from Washington (DCA) to Pittsfield (PSF)
- Flights from Tampa (TPA) to Pittsfield (PSF)
- Flights from Los Angeles (LAX) to Pittsfield (PSF)
- Flights from New York (LGA) to Pittsfield (PSF)
- Flights from Atlanta (ATL) to Pittsfield (PSF)
- Flights from Islip (ISP) to Pittsfield (PSF)
- Flights from Chicago (ORD) to Pittsfield (PSF)
- Flights from Denver (DEN) to Pittsfield (PSF)
- Flights from San Francisco (SFO) to Pittsfield (PSF)
- Flights from Hartford (BDL) to Pittsfield (PSF)
- Flights from Baltimore (BWI) to Pittsfield (PSF)
- Flights from Detroit (DTW) to Pittsfield (PSF)
- Flights from Raleigh (RDU) to Pittsfield (PSF)
- Flights from Houston (IAH) to Pittsfield (PSF)
- Flights from Rochester (ROC) to Pittsfield (PSF)
- Flights from Kansas City (MCI) to Pittsfield (PSF)
- Flights from Miami (MIA) to Pittsfield (PSF)
- Flights from Sarasota (SRQ) to Pittsfield (PSF)
- Flights from Providence (PVD) to Pittsfield (PSF)
- Flights from Buffalo (BUF) to Pittsfield (PSF)
- Flights from St. Louis (STL) to Pittsfield (PSF)
- Flights from Minneapolis (MSP) to Pittsfield (PSF)
- Flights to Pittsfield Municipal
- Flights from Columbus (CMH) to Pittsfield (PSF)
- Flights from West Palm Beach (PBI) to Pittsfield (PSF)
- Flights from Indianapolis (IND) to Pittsfield (PSF)
- Flights from Phoenix (PHX) to Pittsfield (PSF)
- Flights from Allentown (ABE) to Pittsfield (PSF)
- Flights from Seattle (SEA) to Pittsfield (PSF)
- Flights from Wilmington (ILM) to Pittsfield (PSF)
- Flights from Greenville (GSP) to Pittsfield (PSF)
- Flights from White Plains (HPN) to Pittsfield (PSF)
- Flights from Milwaukee (MKE) to Pittsfield (PSF)
- Flights from Portland (PDX) to Pittsfield (PSF)
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights from Montreal (YUL) to Pittsfield (PSF)
- Flights from Memphis (MEM) to Pittsfield (PSF)
- Flights from Las Vegas (LAS) to Pittsfield (PSF)
- Flights from Charleston (CHS) to Pittsfield (PSF)
- Flights from Richmond (RIC) to Pittsfield (PSF)
- Flights from Pensacola (PNS) to Pittsfield (PSF)
- Flights from Fargo (FAR) to Pittsfield (PSF)
- Flights from Ontario (ONT) to Pittsfield (PSF)
- Flights from Madison (MSN) to Pittsfield (PSF)
- Flights from Norfolk (ORF) to Pittsfield (PSF)
- Flights from Cincinnati (CVG) to Pittsfield (PSF)
- Flights from Burlington (BTV) to Pittsfield (PSF)
- Flights from New Haven (HVN) to Pittsfield (PSF)
- Hopscotch Air Nantucket (ACK) to Pittsfield (PSF) flights
- Flights from Newburgh (SWF) to Pittsfield (PSF)
- Flights from Louisville (SDF) to Pittsfield (PSF)
- Flights from Tucson (TUS) to Pittsfield (PSF)
- Hopscotch Air Burbank (BUR) to Pittsfield (PSF) flights
- Flights from Reno (RNO) to Pittsfield (PSF)
- Flights from Barcelona (BCN) to Pittsfield (PSF)
- Flights from Des Moines (DSM) to Pittsfield (PSF)
- Flights from Akron (CAK) to Pittsfield (PSF)
- Flights from State College (SCE) to Pittsfield (PSF)
- Flights from Fort Myers (RSW) to Pittsfield (PSF)
- Flights from St. Petersburg (PIE) to Pittsfield (PSF)
- Hopscotch Air Williamsport (IPT) to Pittsfield (PSF) flights
- Flights from London (LHR) to Pittsfield (PSF)
- Flights from Rochester (RST) to Pittsfield (PSF)
- Flights from Cleveland (CLE) to Pittsfield (PSF)
- Flights from El Paso (ELP) to Pittsfield (PSF)
- Flights from Charlottesville (CHO) to Pittsfield (PSF)
- Flights from Xi'an (XIY) to Pittsfield (PSF)
- Flights from Jacksonville (CRG) to Pittsfield (PSF)
- Flights from Dayton (DAY) to Pittsfield (PSF)
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Atlanta (PDK) to Pittsfield (PSF)
- Flights from Kuwait City (KWI) to Pittsfield (PSF)