
Deals on vacations and trips to Pittsfield
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Pittsfield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Brook Bound Inn
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

The Equinox Golf Resort & Spa
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

Kingston Carriage House
Roundout
Save 100% on your flight
per person
Aug 21 - Aug 25
found 11 hours ago
Roundtrip flight included
Charleston (CHS) to Albany (ALB)
This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.

DoubleTree by Hilton Schenectady Downtown
Seward Place
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
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 24-hour business center, a terrace, and a garden are also on offer.

Gedney Farm
per person
Aug 11 - Aug 14
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Top Pittsfield hotels deals

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $141 total per night
$141 total
Jul 22 - Jul 23
Total includes taxes and fees
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

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $78 total per night
$78 total
Jul 24 - Jul 25
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
$115 nightly
The price is $128 total per night
$128 total
Jul 30 - Jul 31
Total includes taxes and fees
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
Reserve now, pay when you stay
$121 nightly
The price is $135 total per night
$135 total
Jul 13 - Jul 14
Total includes taxes and fees
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 hot tub and perks like free self parking.
Pool
Hot Tub

Hotel On North
297 North Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $211 total per night
$211 total
Jul 21 - Jul 22
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pet friendly
Parking included

Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
Jul 20 - Jul 21
Total includes taxes and fees
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.
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.
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