Pittsfield Vacation Packages 2025/2026 from $321

Pittsfield flight + hotel vacation packages

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

The Wiltwyck

$321

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Kingston Carriage House

Roundout

Save 100% on your flight

$481

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.

Hasbrouck House

Save 100% on your flight

$679

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free valet parking. Enjoy the sauna and perks like free self parking.

Hotel Kinsley

Kingston Stockade District

Save 100% on your flight

$505

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Save 100% on your flight

$673

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Sep 14 - Sep 15

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

FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$88 total

Sep 14 - Sep 15

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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Free Cancellation

$99 nightly

$111 total

Oct 5 - Oct 6

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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

1055 South Street, Pittsfield, MA

$142 nightly

$158 total

Sep 14 - Sep 15

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

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$119 total

Sep 14 - Sep 15

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

Hotel On North

297 North Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$178 total

Sep 28 - Sep 29

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

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

4/5(9 reviews)

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

4.5/5(53 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.

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 $321. 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.