Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

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The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $725, price is now $583 per person
$583
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Save 100% on your flight
Price was $1,085, price is now $770 per person
$770
per person
May 26 - Jun 2
found 16 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $903, price is now $746 per person
$746
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $968, price is now $827 per person
$827
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Catskill Rose Lodging & Dining

Catskill Rose Lodging & Dining

3 out of 5
Price was $702, price is now $600 per person
$600
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
A seasonal outdoor pool, free self parking, and a virtual front desk are featured at this inn. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden is also provided.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $128 total per night
$128 total
Apr 5 - Apr 6
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$127 nightly
The price is $142 total per night
$142 total
Mar 31 - Apr 1
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
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $166 total per night
$166 total
Mar 8 - Mar 9
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
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $125 total per night
$125 total
Mar 8 - Mar 9
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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$132 nightly
The price is $147 total per night
$147 total
Mar 22 - Mar 23
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
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $143 total per night
$143 total
Mar 15 - Mar 16
Total with taxes and fees
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
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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.

Bousquet Ski Area
Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres

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.

Hancock Shaker Village
View of peak foliage in the Berkshires.

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.

Berkshire Museum

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 $583. 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.

Photos of local treasures

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