Pittsfield Vacation Packages 2026 from $642

Pittsfield flight + hotel vacation packages

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

Valley Craft Ales

$642

per person

Sep 17 - Sep 24

found 17 hours ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Hotel Vervana, Trademark Collection by Wyndham

Save 100% on your flight

$767

per person

Sep 17 - Sep 24

found 17 hours ago

Roundtrip non-stop 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.

Brook Bound Inn

Save 100% on your flight

$1,119

per person

Sep 17 - Sep 24

found 17 hours ago

Roundtrip non-stop 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 White House Inn

Save 100% on your flight

$1,020

per person

Sep 17 - Sep 24

found 17 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

The Manchester View

Save 100% on your flight

$1,125

per person

Sep 17 - Sep 24

found 17 hours ago

Roundtrip non-stop flight included

Orlando (MCO) 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.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$173 total

Aug 5 - Aug 6

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 Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$185 total

Jul 12 - Jul 13

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.

Hotel On North

297 North Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$249 nightly

$278 total

Jul 7 - Jul 8

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.

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$68 total

Jul 29 - Jul 30

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.

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$152 total

Aug 2 - Aug 3

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.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$152 nightly

$170 total

Aug 3 - Aug 4

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.

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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 historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 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.

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 $642. 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.