Pittsfield Vacations from $621
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Your Pittsfield Vacation
Our Pittsfield vacation packages give you the power to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this wonderful city. JW Parks Golf Course is among the popular attractions to add to your sightseeing agenda during a trip to Pittsfield. Stop daydreaming and start adventuring. Browse the wide range of options on Expedia today and put your Pittsfield vacation plans in motion!
The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Vacationland Inn & Suites
$983
per person
Jan 8 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Bangor (BGR)
7.6/10 Good! (1,643 reviews)
Really enjoyed staying here. There are some minor maintenance issues in the room, but overall it was a positive experience, the room was clean, decent amenities and worth the price. I will definitely be returning next year. Didn’t do the breakfast so I can’t comment on that.
Reviewed on Oct 16, 2026
Stay near popular Pittsfield attractions
JW Parks Golf Course
This scenic 9-hole course in Pittsfield offers rolling fairways and strategic hazards for all skill levels. Enjoy a post-round meal at the Broken Putter Grille Room, known for its signature sandwiches.
Pittsfield Hotel Deals
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield ME
$208 nightly
$227 total
Oct 19 - Oct 20
Total with taxes and fees
9.8/10 Exceptional! (10 reviews)
"The home appeared to have been recently remodeled. Appliances, fixtures, and furnishings all are new. The home was clean and convenient to where we want to be. Our host was quick to respond to any minor questions that I had. Overall it was a nice place to stay and I would not hesitate to rent the ..."
Reviewed on Sep 23, 2026
Angel Mist Retreat Garage Apartment
Pittsfield ME
$282 nightly
$308 total
Oct 18 - Oct 19
Total with taxes and fees
10/10 Exceptional! (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
Reviewed on Jul 17, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$111 nightly
$121 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Very professional and quiet and clean"
Reviewed on Oct 16, 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 |
Population | 3,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Eaton Mountain, Great Moose Lake and JW Parks Golf Course |
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Frequently asked questions
How much does a Pittsfield vacation package cost?
You'll find cheap prices from $621 on Expedia for your Pittsfield break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
You're likely to find reduced prices and better availability in September, November and December. Explore our cheap Pittsfield vacation packages and you could get some great off-season discounts.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to see the main sights during your Pittsfield vacation. But if you prefer to have some time to unwind or take day trips, consider extending your itinerary.
How to find the best Pittsfield package deals?
Use Expedia's filters to find some terrific Pittsfield package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Pittsfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Pittsfield vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Pittsfield vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates finalized, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Jet off on your ideal getaway to Pittsfield with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait for the next payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up travel deals before they sell out.
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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.
