Find Winery Hotels in Pittsfield, MA
Check availability on Pittsfield Winery Hotels
Top Pittsfield Winery Hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
9.0 out of 10, Wonderful, (1001)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
Elisabeth
$101 nightly
The price is $113
Dec 14 - Dec 15
Total with taxes and fees
East Rock Inn
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
Laura
$131 nightly
The price is $147
Dec 18 - Dec 19
Total with taxes and fees
Berkshire Valley Inn
Williamstown
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
Scott
$134 nightly
The price is $150
Dec 7 - Dec 8
Total with taxes and fees
Gateways Inn & Restaurant
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
Josephine
$169 nightly
The price is $187
Jan 2 - Jan 3, 2026
Total with taxes and fees
Brook Farm Inn
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
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
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Explore a world of travel with Expedia
- Hotels near Berkshire Museum
- Hotels near Berkshire Athenaeum
- Hotels near Colonial Theater
- Hotels near Barrington Stage Company
- Cabin Rentals in Berkshire County
- 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 Ontario (ONT) to Pittsfield (PSF)
- Flights from Madison (MSN) to Pittsfield (PSF)
- Flights from Norfolk (ORF) to Pittsfield (PSF)
- Flights from Pensacola (PNS) to Pittsfield (PSF)
- Flights from Fargo (FAR) 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 Louisville (SDF) to Pittsfield (PSF)
- Flights from Reno (RNO) to Pittsfield (PSF)
- Flights from Tucson (TUS) to Pittsfield (PSF)
- Hopscotch Air Burbank (BUR) to Pittsfield (PSF) flights
- Flights from Newburgh (SWF) to Pittsfield (PSF)
- Flights from Barcelona (BCN) to Pittsfield (PSF)
- Flights from Des Moines (DSM) to Pittsfield (PSF)
- Flights from London (LHR) to Pittsfield (PSF)
- Flights from Panama City (ECP) to Pittsfield (PSF)
- Flights from Fort Myers (RSW) to Pittsfield (PSF)
- Flights from San Jose (SJC) to Pittsfield (PSF)
- Flights from El Paso (ELP) to Pittsfield (PSF)
- Flights from Dayton (DAY) to Pittsfield (PSF)
- Flights from Xi'an (XIY) to Pittsfield (PSF)
- Flights from Leesburg (LEE) to Pittsfield (PSF)
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Kuwait City (KWI) to Pittsfield (PSF)
- Flights from Binghamton (BGM) to Pittsfield (PSF)
- Flights from Jacksonville (CRG) to Pittsfield (PSF)
- Hopscotch Air Williamsport (IPT) to Pittsfield (PSF) flights
- Flights from Washington (IAD) to Pittsfield (PSF)
- Flights from St. Petersburg (PIE) to Pittsfield (PSF)
- Flights from San Diego (MYF) to Pittsfield (PSF)