Pittsfield Vacation Packages 2025/2026 from $344

Pittsfield flight + hotel vacation packages

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Save 100% on your flight

$344

per person

Nov 8 - Nov 15

found 12 hours ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

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.

Gedney Farm

Save 100% on your flight

$505

per person

Nov 6 - Nov 10

found 7 hours ago

Roundtrip flight included

Pittsburgh (PIT) 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, a garden, and a communal living room are also on offer.

The White House Inn

Save 100% on your flight

$549

per person

Dec 9 - Dec 16

found 1 day ago

Roundtrip flight included

New York (JFK) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace and a garden are also provided.

The Constance by the Lenox Collection

Save 100% on your flight

$658

per person

Nov 6 - Nov 10

found 7 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Albany (ALB)

A gym, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A library, express check-out, and wedding services are also on offer.

Brook Bound Inn

Save 100% on your flight

$969

per person

Nov 9 - Nov 16

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

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

Nov 2 - Nov 3

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

$103 nightly

$115 total

Nov 2 - Nov 3

Total with taxes and fees

Pool

Pet friendly

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$114 total

Nov 2 - Nov 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.

Breakfast included

Pet friendly

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street, Pittsfield, MA

$144 nightly

$160 total

Nov 2 - Nov 3

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

Hotel On North

297 North Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$137 total

Nov 3 - Nov 4

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

Berkshire Inn

150 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$84 total

Nov 4 - Nov 5

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

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 family-friendly 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 $344. 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.