Pittsfield Vacation Packages 2025 from $437

Pittsfield flight + hotel vacation packages

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

Wilder House Berkshires

Save 100% on your flight

per person

Mar 14 - Mar 18

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.

The Equinox Golf Resort & Spa

Save 100% on your flight

per person

Jan 23 - Jan 26

found 3 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Howard Hotel

Save 100% on your flight

per person

Feb 13 - Feb 17

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

Free WiFi in public areas, a hair salon, and luggage storage are available at this hotel. A virtual front desk are provided for your convenience.

Gedney Farm

Save 100% on your flight

per person

Mar 14 - Mar 18

found 4 hours ago

Roundtrip 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, a garden, and a communal living room are also on offer.

Little Cat Lodge

Save 100% on your flight

per person

Mar 14 - Mar 18

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and free self parking. Free WiFi in public areas, a garden, and a picnic area are also on offer.

Top Pittsfield hotels deals

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

One West Street, Pittsfield, MA

Free Cancellation

$111

includes taxes & fees

$99 per night

Jan 5 - Jan 6, 2025

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.

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$105

includes taxes & fees

$94 per night

Jan 2 - Jan 3, 2025

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

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

$204

includes taxes & fees

$185 per night

Jan 1 - Jan 2, 2025

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 spa tub and perks like free self parking.

Pool

Hot Tub

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$163

includes taxes & fees

$146 per night

Dec 31 - Jan 1, 2025

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

Berkshire Inn

150 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$87

includes taxes & fees

$77 per night

Dec 24 - Dec 25

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

Chic Pittsfield Home With A View!

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This vacation home includes a garden and barbecue grills.

Kitchen

Washer

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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 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.

Colonial Theater

3.5/5(3 reviews)

You can make plans for a show at Colonial Theater 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 $437. 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.