Pittsfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Wilder House Berkshires
Save 100% on your flight
per person
Mar 14 - Mar 18
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.
The Equinox Golf Resort & Spa
Save 100% on your flight
per person
Jan 23 - Jan 26
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Gedney Farm
Save 100% on your flight
per person
Mar 14 - Mar 18
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.
Little Cat Lodge
Save 100% on your flight
per person
Mar 14 - Mar 18
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and free self parking. Free WiFi in public areas, a garden, and a picnic area are also on offer.
Top Pittsfield hotels deals
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
One West Street, Pittsfield, MA
Free Cancellation
The price is $111 per night
$111
includes taxes & fees
$99 per night
Jan 5 - Jan 6, 2025
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.
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $105 per night
$105
includes taxes & fees
$94 per night
Jan 2 - Jan 3, 2025
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 a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
The price is $204 per night
$204
includes taxes & fees
$185 per night
Jan 1 - Jan 2, 2025
This lodge features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
Pool
Hot Tub
Hilton Garden Inn Lenox Pittsfield
1032 South Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $163 per night
$163
includes taxes & fees
$146 per night
Dec 31 - Jan 1, 2025
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
Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $87 per night
$87
includes taxes & fees
$77 per night
Dec 24 - Dec 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
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 quaint 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.
Colonial Theater
3.5/5(3 reviews)
You can make plans for a show at Colonial Theater during your trip to Pittsfield. Wander the lakeside in this quaint area.
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