Pittsfield Vacation Packages 2025 from $503

Pittsfield flight + hotel vacation packages

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

Hampton Inn Schenectady Downtown

Seward Place

Save 100% on your flight

per person

Jul 4 - Jul 9

found 19 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Albany (ALB)

This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a grocery/convenience store, and a lobby fireplace are also on offer.

DoubleTree by Hilton Schenectady Downtown

Seward Place

per person

Aug 28 - Sep 1

found 1 day ago

Roundtrip flight included

Washington (IAD) to Albany (ALB)

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 24-hour business center, a terrace, and a garden are also on offer.

Hilton Garden Inn Albany Airport

per person

Jul 4 - Jul 9

found 20 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Albany (ALB)

This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

The Equinox Golf Resort & Spa

per person

Jul 25 - Jul 27

found 19 hours ago

Roundtrip flight included

Detroit (DTW) 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.

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

per person

Aug 3 - Aug 8

found 19 hours ago

Roundtrip flight included

Washington (IAD) to Albany (ALB)

This hotel 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 free perks like buffet breakfast and free self parking.

Top Pittsfield hotels deals

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Jun 15 - Jun 16

Total includes 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 & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

Free Cancellation

$109 nightly

$122 total

Jun 8 - Jun 9

Total includes 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

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$155 total

Jun 4 - Jun 5

Total includes taxes and fees

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

$109 nightly

$122 total

Jun 4 - Jun 5

Total includes taxes and fees

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

Berkshire Inn

150 W Housatonic St, Pittsfield, MA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$104 total

Jun 10 - Jun 11

Total includes 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

The Central Downtown Inn & Suites

20 W Housatonic St., Pittsfield, MA

$119 nightly

$133 total

Jun 5 - Jun 6

Total includes taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.

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 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.

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 $503. 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.