Pittsfield Vacation Packages 2026 from $639

Pittsfield flight + hotel vacation packages

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

Hotel Vervana, Trademark Collection by Wyndham

$639

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 free perks like continental breakfast and free self parking.

South Shire

$764

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

Aspen At Manchester

$678

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

Brook Bound Inn

$881

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 And Spa

Manchester Village Historic District

$954

per person

Dec 30 - Jan 2

found 1 day 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.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$128 total

Nov 19 - Nov 20

Total with taxes and fees

This aparthotel 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

$142 nightly

$158 total

Nov 1 - Nov 2

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and luggage storage are also offered on site.

Pet friendly

Parking included

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

Free Cancellation

$95 nightly

$106 total

Nov 19 - Nov 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

$65 nightly

$72 total

Nov 5 - Nov 6

Total with 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

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Nov 15 - Nov 16

Total with 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

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$99 nightly

$111 total

Oct 22 - Oct 23

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.

Pet friendly

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.

Stay near popular Pittsfield attractions

A snow-covered town with buildings, a ski lift, and a mountain in the background.

Bousquet Ski Area

8.2/10 (48 reviews)

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

See properties

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 $639. 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.