Pittsfield Vacations from $527
Book a Hotel + Flight or Car together to unlock savings
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.
Glen Mary Apartments
$1,122
per person
Oct 25 - Oct 29
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Bangor (BGR)
9/10 Wonderful! (2 reviews)
First floor of property was under construction and looked a bit shabby. Overall unit was good although electronics took some getting used to.
Reviewed on Aug 5, 2025
Sand Bar Cottage Inn
$860
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.8/10 Exceptional! (424 reviews)
We loved our stay. The location was perfect - easy walking distance to downtown and just a short walk from the Bar Harbor trail sandbar that is only passable at low tide. The staff were great and the savory and sweet breakfast options were delicious! Plus the water pressure in the shower was fantastic! Would definitely stay again.
Reviewed on Aug 25, 2026
Mount Battie Inn
$1,082
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.8/10 Excellent! (335 reviews)
The staff were very kind and available. The landscaping and common spaces were immaculate. The room was quite comfortable, although the bed was not.
Reviewed on Aug 24, 2026
Heathwood Inn
$766
per person
Oct 25 - Oct 29
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Bangor (BGR)
8.2/10 Very Good! (204 reviews)
This was a great place to stay. Was very comfortable and the inn was a beautiful place. I was surprised, I thought that breakfast was on site. Breakfast is offsite and I never wound up eating it so that is something to remember if you’re expecting to be able to walk downstairs to eat breakfast. But overall very comfortable and a great place to stay. It was extremely relaxing to be there and quiet.
Reviewed on Aug 27, 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
$211 nightly
$230 total
Sep 7 - Sep 8
Total with taxes and fees
9.8/10 Exceptional! (8 reviews)
"I recommend this property to anyone staying in the Pittsfield area. I’ve already suggested it to our friends who live there as great option for guests. Very clean and comfortable and a good value."
Reviewed on Jul 28, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$130 nightly
$142 total
Sep 13 - Sep 14
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
"Rooms were very clean. Staff was very helpful."
Reviewed on Aug 31, 2026
The Elmwood
455 Kennedy Memorial Dr Waterville ME
Fully refundableReserve now, pay when you stay
$127 nightly
$138 total
Sep 23 - Sep 24
Total with taxes and fees
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 $527 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.