Pittsfield Vacations from $862
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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.
Whitehall
Price was $1,250, price is now $1,052 per person
$1,052
per person
Oct 1 - Oct 5
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.2/10 Wonderful! (636 reviews)
Great place to stay. They really make you feel at home. My room needed a minor fix and they took care of it right away. My wife needed a soda and they found her one immediately. The inn is close to town and easy to get to. Wish our stay had been longer and will absolutely return if given the chance.
Reviewed on Jul 16, 2026
Moseley Cottage Inn & Town Motel
Downtown Bar Harbor
Price was $1,241, price is now $1,044 per person
$1,044
per person
Aug 28 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.4/10 Exceptional! (589 reviews)
It's an older building, but well maintained... the only (minor) issue we had in our room was one blind got stuck closed.
The staff was super accommodating for a late arrival... when we phoned they gave clear instructions on how to access our room, and even managed to provide us breakfast the next morning despite our arrival time being well after the cut-off to submit a breakfast order for the next day.
Breakfast was impressively good, with a nice array of choices and great quality delivered promptly to your room at (or even slightly before) the requested time.
Reviewed on Jul 17, 2026
Stay near popular Pittsfield attractions
Pittsfield Hotel Deals
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome
Pittsfield ME
$208 nightly
The price is $227 total per night from Jul 23 to Jul 24
$227 total
Jul 23 - Jul 24
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Pittsfield ME
$282 nightly
The price is $308 total per night from Jul 26 to Jul 27
$308 total
Jul 26 - Jul 27
Total with taxes and fees
10/10 Exceptional! (14 reviews)
"We were there for the Common Ground Fair in Unity. We spent very little time in the facility, 2 short evenings only, but we loved the peace and quiet of the countryside"
Reviewed on Sep 26, 2025
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from Aug 16 to Aug 17
$141 total
Aug 16 - Aug 17
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"The only complaint I have is that we didn't get our whoopy pies we were there for 5 days and they didn't come in :( but everything else was great"
Reviewed on Jul 17, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
