Pittsfield Vacation Packages 2025/2026 from $359

Pittsfield flight + hotel vacation packages

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

The Clocktower Hotel at Century House, an Ascend Collection Hotel

$359

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to Albany (ALB)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Vacation Village in the Berkshires

$494

per person

Feb 14 - Feb 17

found 14 hours ago

Roundtrip non-stop flight included

San Jose (SJC) to Albany (ALB)

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Hotel Brookmere & Arbor Spa

$499

per person

Feb 14 - Feb 17

found 14 hours ago

Roundtrip non-stop flight included

San Jose (SJC) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

South Shire

$566

per person

Feb 13 - Feb 16

found 22 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Albany (ALB)

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and concierge services are also on offer.

Aspen At Manchester

$761

per person

Feb 13 - Feb 16

found 22 hours ago

Roundtrip non-stop flight included

San Juan (SJU) 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.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$135 total

Dec 7 - Dec 8

Total with 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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$93 nightly

$104 total

Nov 30 - Dec 1

Total with 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

Hotel On North

297 North Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$149 total

Dec 22 - Dec 23

Total with 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

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$104 total

Nov 30 - Dec 1

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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street Pittsfield MA

Free Cancellation

$95 nightly

$106 total

Dec 7 - Dec 8

Total with taxes and fees

This hotel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, laundry facilities, and concierge services are also on offer.

Pool

Hot Tub

Hilton Garden Inn Lenox Pittsfield

1032 South Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$124 total

Dec 7 - Dec 8

Total with taxes and fees

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

Don't see what you're looking for?

See all available properties in Pittsfield

View all properties

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.

Colonial Theater

You can make plans for a show at Colonial Theater 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 $359. 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.