Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $585, price is now $511 per person
$511
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Albany (ALB)
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $969, price is now $836 per person
$836
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Albany (ALB)
This hotel features 2 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the free buffet breakfast each morning.
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
Price was $775, price is now $668 per person
$668
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Albany (ALB)
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 24-hour gym and perks like free self parking.
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Downtown Albany
Price was $813, price is now $714 per person
$714
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Albany Airport Inn

Albany Airport Inn

2.5 out of 5
Price was $628, price is now $556 per person
$556
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Albany (ALB)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free perks include buffet breakfast, free self parking, and an area shuttle.

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
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
Total with taxes and fees
This aparthotel 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.
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night
$68 total
Aug 27 - Aug 28
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.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$131 nightly
The price is $146 total per night
$146 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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
$119 nightly
The price is $133 total per night
$133 total
Sep 13 - Sep 14
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, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking.
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
$114 nightly
The price is $127 total per night
$127 total
Aug 30 - Aug 31
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.
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $200 total per night
$200 total
Sep 7 - Sep 8
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.
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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.

Stay near popular Pittsfield attractions

A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 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.
See properties

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 $511. 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

Browse Pittsfield vacation photos for more inspiration

A historic building with classical architecture, a traffic light, and a yellow taxi.
A stone building with a red door and a tree with pink flowers in front.
A brick building with a clock and an American flag.
A stone church with arched windows and a central tower, surrounded by trees.
A street lined with autumn trees, a street lamp, and parked cars.

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