Pittsfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.510.287 ₫ per night from 9 Aug to 10 Aug
3.510.287 ₫
4.507.840 ₫ total
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (1,029 reviews)
"Very spacious. Kitchen is a plus"

Reviewed on 11 Jul 2026

Berkshire Mountain Lodge
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
Fully refundable
The price is 4.137.367 ₫ per night from 16 Jul to 17 Jul
4.137.367 ₫
4.621.439 ₫ total
16 Jul - 17 Jul
includes taxes & fees
9.4/10 Exceptional! (127 reviews)
"This place is great. My favorite. Hot Tub is HOT!"

Reviewed on 7 Jul 2026

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 6.540.981 ₫ per night from 14 Jul to 15 Jul
6.540.981 ₫
7.306.275 ₫ total
14 Jul - 15 Jul
includes taxes & fees
9.6/10 Exceptional! (873 reviews)
"The stay was wonderful! Great staff! We were heading to Tanglewood and they provided directions that were excellent. The room was beautiful, clean, and quiet."

Reviewed on 5 Jul 2026

Hotel On North
See all 1,340 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.

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)
Step back in time at this living history museum showcasing Shaker life and craftsmanship. Marvel at the iconic Round Stone Barn and explore 20 historic buildings filled with over 22,000 authentic artefacts.
See properties

Frequently asked questions

How much does a Pittsfield holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Pittsfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
January, March and April are the best times to search for cheap Pittsfield holiday packages. Travelling in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to check out the major sights during your Pittsfield holiday. But if you prefer to have more time to kick back or take day trips, think about extending your itinerary.
Is it worth booking a holiday package to Pittsfield?
Pittsfield is a good holiday destination with attractions like Bousquet Ski Area among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Pittsfield holiday promises fun for everyone.
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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield holiday as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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.
How to plan a trip to Pittsfield?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Pittsfield.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Pittsfield.
  3. Decide how long to go for: Now that you know more about Pittsfield, you can work out the ideal length of your holiday. Create a draft plan and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Pittsfield holiday package that brings all your bookings together.

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