Pittsfield Vacations from $543
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
$543
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
Stay near popular Pittsfield attractions
Harold Conrad Square
This quaint community park in Pittsfield offers a peaceful retreat for quiet reflection and leisurely walks. Bring a picnic lunch and explore the historic churches nearby for a charming small-town experience.
Drake Field
Drake Field hosts the colorful annual Rotary Balloon Festival, a highlight of Pittsfield's summer. Stroll the riverside trail or relax in the gazebo while watching hot air balloons fill the August sky.
Josiah Carpenter Library
This 1901 neoclassical library designed by Butterfield serves as Pittsfield's community learning hub. Browse the collection while admiring the historical architecture that creates a charming, quiet atmosphere.
Scenic Theatre
The Scenic Theatre showcases local talent through vibrant community productions in historic Pittsfield. Catch an intimate evening performance of classic plays or contemporary musicals in this charming cultural hub.
Pittsfield Hotel Deals
The Centennial
96 Pleasant St Concord NH
Fully refundableReserve now, pay when you stay
$151 nightly
$164 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"I was excited to stay here and the staff is exceptionally. My bathroom was dirty. The shower had mold all over it. The sink was not cleaned at all! The shower glass door had soap scum all over it. I tried to clean it with soap and water and it came clean. The complimentary breakfast consisted with ..."
Reviewed on Oct 26, 2026
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
$167 nightly
$181 total
Nov 3 - Nov 4
Total with taxes and fees
9.6/10 Exceptional! (237 reviews)
"Property was beautiful. Check your smore pack right at check in. It’s an extra cost otherwise known as an amenity fee. Ours was not accurate. I didn’t notice till late and notified the next day so they can work on the process for other guests. I’m sure they would have fixed it that day had I noticed ..."
Reviewed on Oct 25, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$101 nightly
$110 total
Nov 1 - Nov 2
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"Great location nice people very helpful room was beautiful theonly thong the TV was not coming in to good we called about it it was do to the cable company .very bad connection all and all great place"
Reviewed on Oct 25, 2026
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 |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Population | 1,600 |
More vacations you might like
Frequently asked questions
How much does a Pittsfield vacation package cost?
You'll find cheap prices from $543 on Expedia for your Pittsfield escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
You can generally find lower rates and better availability in November, December and January. Explore our cheap Pittsfield vacation packages and you could land some great off-season deals.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to tick off the main sights during your Pittsfield vacation. However, if you'd like to have more time to relax or go on day tours, think about extending your itinerary.
How to find the best Pittsfield package deals?
Use Expedia's filters to find some tempting Pittsfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize your Pittsfield escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pittsfield?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pittsfield adventure.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Set off on your perfect trip to Pittsfield with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
