Pittsfield Vacation Packages 2025 from $394

Pittsfield flight + hotel vacation packages

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

Lodges At Cresthaven

per person

Apr 18 - Apr 20

just found

Roundtrip flight included

Indianapolis (IND) to Albany (ALB)

A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and barbecue grills are also provided.

Hilton Garden Inn Saratoga Springs

per person

Apr 18 - Apr 20

just found

Roundtrip flight included

Indianapolis (IND) to Albany (ALB)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Free self parking, a garden, and a lobby fireplace are also offered.

The Springwater B&B

per person

Apr 18 - Apr 20

just found

Roundtrip flight included

Indianapolis (IND) to Albany (ALB)

This bed & breakfast features a restaurant, a 24-hour gym, and a bar/lounge. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden, a lobby fireplace, and luggage storage are also on offer.

The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

per person

Apr 18 - Apr 20

found 1 hour ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

This smoke-free hotel features a casino and 5 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Saratoga Casino Hotel

per person

Apr 18 - Apr 20

found 1 hour ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.

Top Pittsfield hotels deals

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

One West Street, Pittsfield, MA

Free Cancellation

$116

includes taxes & fees

$104 per night

Feb 28 - Mar 1

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

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

$131

includes taxes & fees

$119 per night

Mar 23 - Mar 24

This lodge features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Hotel On North

297 North Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$122

includes taxes & fees

$109 per night

Mar 2 - Mar 3

This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, dry cleaning, and luggage storage are also offered.

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

$112

includes taxes & fees

$100 per night

Feb 24 - Feb 25

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

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$146

includes taxes & fees

$131 per night

Feb 25 - Feb 26

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

FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$77

includes taxes & fees

$69 per night

Feb 24 - Feb 25

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

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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

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 $394. 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.