Pittsfield Vacation Packages 2025/2026 from $427

Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Vervana, Trademark Collection by Wyndham

per person

Sep 6 - Sep 10

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

The Equinox Golf Resort & Spa

Save 100% on your flight

per person

Sep 6 - Sep 10

found 2 hours ago

Roundtrip flight included

Chicago (ORD) 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.

The Manchester View

per person

Sep 6 - Sep 10

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Brook Bound Inn

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Valley Craft Ales

per person

Sep 6 - Sep 10

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also provided.

Top Pittsfield hotels deals

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Free Cancellation

$123 nightly

$137 total

Aug 4 - Aug 5

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

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$141 total

Jul 30 - Jul 31

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

$70 nightly

$79 total

Aug 25 - Aug 26

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

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$116 total

Aug 17 - Aug 18

Total includes taxes and fees

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

Hotel On North

297 North Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$211 total

Aug 3 - Aug 4

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

$86 nightly

$97 total

Jul 27 - Jul 28

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

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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

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

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

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.

Frequently asked questions

How much are vacation packages to Pittsfield?

With a Travelocity vacation package, you can live it up in Pittsfield for as low as $427. Flights, hotels and experiences — we've got you. You can save some cash just for combining your bookings. With all of that taken care of before you even set off, you won't have to worry about a thing.

How long should my Pittsfield vacation be?

Your Pittsfield break can be as short or as long as you'd like it to be, but the majority of travelers stay roughly 2 nights. Hoping to veer off the beaten path and discover some hidden gems? Book a couple more nights and see another side of this place.

Where can I get the best vacation package deals for Pittsfield?

It's hard to beat Travelocity when it comes to putting together your Pittsfield package deal. There are at least 400 airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to tick another exciting place off your to-do list.

Why should I book my Pittsfield vacation bundle with Travelocity?

From our 24/7 support to our range of exhilarating destinations, we are dedicated to fulfilling your vacation dreams. All you'll have to do is click and book — our Price Match Guarantee will ensure you get the best deal.

Can I save money on my Pittsfield car rental if I combine it with hotels and flights?

With a Pittsfield vacation package, you can bundle your hotel, car and flight bookings and save a ton. If you want to uncover the best of this fantastic area, why not start with Times Square? This renowned sight is 120 mi from Pittsfield. With your own rental car, you'll be there in no time.

Which airport is best for Pittsfield?

Bradley Intl. Airport (BDL) is 45 mi from the city center and is the starting point for many exciting adventures. Alternatively, Albany Intl. Airport (ALB) is 35 mi away from central Pittsfield and Hartford, CT (HFD-Hartford - Brainard) is 60 mi away from central Pittsfield.

What is there to do in Pittsfield?

Pittsfield has plenty of places to explore, such as Bousquet Ski Area and Barrington Stage Company. These two impressive attractions top most travelers' itineraries.

Where should I stay when visiting Pittsfield?

Many travelers opt to spend their nights at the Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. It's the perfect base for your Pittsfield vacation.