Pittsfield Vacation Packages 2026 from $1,050

Pittsfield flight + hotel vacation packages

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

Tru By Hilton Albany Airport, NY

$1,050

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Hyatt Place Albany/Downtown

Downtown Albany

$1,063

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Hampton Inn Albany-Wolf Road (Airport)

$1,051

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.

Park Manor Hotel

$1,122

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.

Best Western Plus Franklin Square Inn Troy/Albany

$1,086

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. A business center, a terrace, and a garden 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

$113 nightly

$126 total

May 25 - May 26

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

Hotel On North

297 North Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$144 total

May 24 - May 25

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$122 nightly

$136 total

May 27 - May 28

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, free WiFi in public areas, and free valet parking. 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

$110 nightly

$123 total

May 25 - May 26

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

$127 nightly

$142 total

May 28 - May 29

Total with taxes and fees

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

Pool

Hot Tub

Berkshire Inn

150 W Housatonic St Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$83 total

May 26 - May 27

Total with 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

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.

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.

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 $1,050. 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.