Pittsfield Vacation Packages

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Top Pittsfield hotel deals

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
The price is $97 per night
$97
per night
May 30 - May 31
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.
Pet friendly
Breakfast available
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
The price is $165 per night
$165
per night
May 28 - May 29
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.
Hot Tub
Pool
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $112 per night
$112
per night
May 28 - May 29
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.
Pet friendly
Breakfast included
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $168 per night
$168
per night
May 30 - May 31
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.
Pet friendly
Breakfast available
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $81 per night
$81
per night
May 28 - May 29
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
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
May 28 - May 29
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.
Pet friendly
Breakfast available
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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 in Pittsfield

Image for Bousquet Ski Area

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.

Bousquet Ski Area
Image for Berkshire Museum

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.

Berkshire Museum
Image for Hancock Shaker Village

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.

Hancock Shaker Village

Frequently asked questions

How much are vacation packages to Pittsfield?
Treat yourself to a memorable experience in Pittsfield with a vacation package starting at just . Booking hotels, flights and tours with Travelocity is a piece of cake. And even better, our deals will leave you with more savings for fun activities.
How long should my Pittsfield vacation be?
The majority of travelers reserve a hotel for 2 nights in Pittsfield. But that doesn’t necessarily mean you have to do the same. How long you spend here depends on what you want to do on your vacation. If you hope to familiarize yourself with every part of this wonderful place, stay another night or two (or even longer!).
Where can I get the best vacation package deals for Pittsfield?
Travelocity is where to go to score a sensational Pittsfield package deal. Select from 400 partner airlines and 1,000,000 properties across the globe and create a vacation package that fits your style. With so many options at hand, it’s easy to plan your next exciting getaway.
Why should I book my Pittsfield vacation package with Travelocity?
Whether you’re planning an epic vacation or a last-minute trip, we have many attractive destinations to choose from at a great price. In addition, we provide support 24/7, high-quality service and a Price Match Guarantee. Save yourself money and time and secure your dream vacation today.
Will I save money on my Pittsfield car rental if I combine it with my hotel or flight?
Combining your car, hotel and flight into a Pittsfield vacation package is a great way to score the best deal. Plus, having your own set of wheels gives you total freedom to make your way to all the landmarks you’re hoping to explore. Sitting 120 mi away from Pittsfield, Times Square is one attraction that should be on your agenda. Turn up the tunes and make a day trip of it.
What is the best time of year to go to Pittsfield?
That all comes down to whether you’d like to save cash or visit Pittsfield at its most exciting. The quietest time to see this part of the world is October, November and December. If you’d like to experience this destination at its peak, consider January, February and July. More interested in saving your hard-earned cash? The cheapest month is . typically has the highest prices.
Which airport is best for Pittsfield?
Bradley Intl. Airport (BDL) (45 mi away from downtown), Albany Intl. Airport (ALB) (35 mi away from central Pittsfield) and Hartford, CT (HFD-Hartford - Brainard) (60 mi away from central Pittsfield) are all top options for Pittsfield.
What is there to do in Pittsfield?
While venturing off the beaten track can be rewarding, you shouldn’t miss the big-name sights that make a destination famous. Bousquet Ski Area and Hancock Shaker Village are a couple of them in Pittsfield.
Where should I stay when visiting Pittsfield?
If you’re looking for someplace comfortable to lay your head, have a look at the Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. It’s the top pick for many visitors.