Pittsfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Lake George NY
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Albany (ALB)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Limo/town car service, a garden, and a picnic area are also on offer.
Gideon Putnam Resort And Spa
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Albany (ALB)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Holiday Inn Saratoga Springs, an IHG Hotel
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Albany (ALB)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Top Pittsfield hotels deals
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
One West Street, Pittsfield, MA
Free Cancellation
The price is $141 per night
$141
per night
Jun 19 - Jun 20
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
The price is $185 per night
$185
per night
Jun 18 - Jun 19
This lodge features an indoor pool and a gym. Enjoy the spa tub and perks like free self parking and free WiFi. A business center, a picnic area, and laundry facilities are also on offer.
Pool
Hot Tub
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
Jun 23 - Jun 24
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Pet friendly
Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $90 per night
$90
per night
Jun 24 - Jun 25
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is provided and the front desk is staffed around-the-clock.
Pool
Parking included
Hilton Garden Inn Lenox Pittsfield
1032 South Street, Pittsfield, MA
The price is $215 per night
$215
per night
Jun 23 - Jun 24
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A terrace, a snack bar/deli, and a grocery/convenience store are also on offer.
Pool
Pet friendly
Hotel Downstreet
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
Jun 18 - Jun 19
This hotel features an indoor pool and a 24-hour gym. Enjoy the spa tub and perks like free self parking and free WiFi. A 24-hour business center, express check-out, and luggage storage are also on offer.
Pool
Hot Tub
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.
Popular places to visit
Bousquet Ski Area
4/5(9 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Berkshire Museum
You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Hancock Shaker Village
4.5/5(53 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
Photos of local treasures
Browse Pittsfield vacation photos for more inspiration
Frequently asked questions
Top all inclusive vacation packages with airfare
Book a vacation to Pittsfield
Most popular
Hotels
Hotels in FalmouthHotels in New BedfordHotels in West SpringfieldHotels in RockportHotels in WorcesterHotels in WilliamstownHotels in HyannisHotels in LenoxHotels in GloucesterHotels in BrocktonHotels in HaverhillHotels in SturbridgeHotels in NorthamptonHotels in LowellHotels in NantucketHotels in MarlboroughHotels in ChicopeeHotels in FoxboroHotels in AmherstHotels in SpringfieldHotels in ProvincetownHotels in PlymouthHotels in Oak BluffsHotels in Lawrence
Cars
Activities