Pittsfield Vacations from $464

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Your Pittsfield Vacation

When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.

The Latest Pittsfield vacation packages

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

South Shire

4 out of 5
Price was $576, price is now $464 per person
$464
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (116 reviews)
Very cool rooms. Al different and many with fireplaces. Friendly staff

Reviewed on Oct 31, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $826, price is now $549 per person
$549
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.

Reviewed on Nov 21, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $881, price is now $589 per person
$589
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
Everything was great

Reviewed on Nov 24, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $896, price is now $668 per person
$668
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (531 reviews)
Staff were awesome . The owners are the greatest people . Their son went above and beyond for us. Our view and room was unbelievable. The boathouse is so inviting, great opportunity to meet people, and food outstanding. John the bartender is the best!!! Highly recommend this place !!!

Reviewed on Nov 23, 2025

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $949, price is now $797 per person
$797
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Great location Everything updated Pleasant greeting in lobby

Reviewed on Nov 25, 2025

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Discover the most popular places to visit in Pittsfield

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.

Bousquet Ski Area
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

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.

Colonial Theater

Pittsfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Dec 7 to Dec 8
$135 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (768 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.

Reviewed on Nov 26, 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$99 nightly
The price is $111 total per night from Dec 26 to Dec 27
$111 total
Dec 26 - Dec 27
Total with taxes and fees
8/10 Very Good! (973 reviews)
The room was clean, and staff who checked us in was both courteous and informative.

Reviewed on Nov 28, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Dec 4 to Dec 5
$104 total
Dec 4 - Dec 5
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
We stay here every Thanksgiving week and it is always a pleasure with the friendly staff, nice clean and orderly room and great breakfast. It is top rate.

Reviewed on Nov 27, 2025

Best Western Plus Berkshire Hills Inn & Suites
See all 1,337 properties in Pittsfield
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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Population
43,300
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Bousquet Ski Area, Colonial Theater and Barrington Stage Company

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You can grab a vacation package to this popular destination from $464 on Expedia. But how much your vacation to Pittsfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
October, November and December are great times to look for cheap Pittsfield vacation packages. Opting to travel in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Pittsfield?
The ideal duration of your Pittsfield vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Pittsfield?
Pittsfield offers everything you need for an unforgettable getaway. Begin your Pittsfield vacation on a high note by checking out major attractions like Bousquet Ski Area.
How to find the best Pittsfield package deals?
Landing a cheap Pittsfield package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Pittsfield package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield trip should be a relaxing escape from your daily routine, not a source of money worries. So to give you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.