
Pittsfield Vacations from $1,172
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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.


3Bedroom2Bath CarriageHouse Pet Friendly
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
7.4/10 Good! (3 reviews)
Loved the charm, cleanliness, decor and location. However, internet was so bad we couldn’t watch more than a few seconds of YouTube at a time. Upstairs shower had the lowest flow we’ve ever seen, even with volume turned up to maximum. Dishwasher was commercial and required many manual steps lifting basket, etc and special soap that we never found. Easier to hand wash. No laundry and outdoor light didn’t work at night so we stepped in dog pooh getting out of the car when we arrived. Beautiful little place that needs some attention.
Reviewed on Oct 11, 2023

Bar Harbor Main Street Apartments
Downtown Bar Harbor
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.2/10 Wonderful! (5 reviews)
Very clean, modern space. Property owner was very informative and gave perfect instructions for check in/out.
Apt was in great location, at end of village, in quiet area of town, but within walking distance to everything, no need to drive for Village activities. Included all necessities. Only upgrade I would suggest would be to add a full length mirror in the bedrooms or somewhere in apt. Otherwise, no complaints! Would definitely recommend and stay again!!
Reviewed on Jul 29, 2025

3BedroomApt Pool CampFire PlayArea
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
8/10 Very Good! (3 reviews)
Nice spot that is very close to bar harbor. Very clean and great for a large amount of people.
Reviewed on Jun 30, 2025

Discover the most popular places to visit in Pittsfield
JW Parks Golf Course
Enjoy a round of golf in Pittsfield at JW Parks Golf Course. Make some time to visit the shops while you're in the area.
Pittsfield Hotel Deals

Family, Friends and Fun for all
Pittsfield
$357 nightly
The price is $389 total per night from Aug 24 to Aug 25
$389 total
Aug 24 - Aug 25
Total includes taxes and fees
Great stay, would stay again
"The house was as described, plenty of space for the whole family, we had a stay of 9 with no issues. Property owner was onsite and awaiting our arrival, l can't say that's a normal thing, but was very helpful in learning our way around the property. The location was great for us, the drive to the ..."
Reviewed on Jul 30, 2025

Angel Mist Retreat Garage Apartment
Pittsfield
$284 nightly
The price is $310 total per night from Aug 25 to Aug 26
$310 total
Aug 25 - Aug 26
Total includes taxes and fees
10/10 Exceptional! (10 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
Reviewed on Jul 23, 2025

Fireside Inn & Suites Waterville
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Aug 31 to Sep 1
$162 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Attached to the hotel is the Governor's restaurant (the pictures that show bakery items under glass). Pool and hot tub are well maintained, I see maintenance and staff all around the property from early hours until late. Grab and Go breakfast choices on par with many breakfast options from most hotel ..."
Reviewed on Aug 13, 2025
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.
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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.