Pittsfield Vacation Packages
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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!
Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Country Inn at The Mall
Price was CA $1,391, price is now CA $1,263 per person
CA $1,263
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.4/10 Exceptional! (2,440 reviews)
Just had hip replacement surgery in Portland & this facility was an absolute Blessing for me to break up my 6 hr commute back home. Fully handicapped room was perfect & staff was friendly and helpful.
Reviewed on Jun 24, 2026
Eden Village Motel & Cottages
Price was CA $4,455, price is now CA $3,891 per person
CA $3,891
per person
Jul 25 - Aug 1
found 11 hours ago
Roundtrip flight included
Montreal (YMQ) to Bangor (BGR)
8.8/10 Excellent! (264 reviews)
Very clean and nice! Will be booking again if so come back up to Maine.
Reviewed on Jun 24, 2026
Hotel Ursa
Price was CA $1,396, price is now CA $1,266 per person
CA $1,266
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.6/10 Exceptional! (713 reviews)
Spotless clean and comfortable hotel right on the beautiful UMaine campus. Polite and helpful staff, Good cafe in the main hotel building, and it's an easy walk or drive into downtown Orono for some good restaurants.
Reviewed on Jun 22, 2026
Moseley Cottage Inn & Town Motel
Downtown Bar Harbor
Price was CA $1,990, price is now CA $1,829 per person
CA $1,829
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Bangor (BGR)
9.4/10 Exceptional! (578 reviews)
Breakfast was amazing. Staff very friendly. Great location to downtown Bar harbor. Easily walkable to all shops and restaurants. Good parking.
Reviewed on Jun 23, 2026
Pittsfield Hotel Deals
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome
Pittsfield ME
The price is CA $169 per night from Jun 28 to Jun 29
CA $169
CA $323 total
Jun 28 - Jun 29
includes taxes & fees
Angel Mist Retreat Garage Apartment
Pittsfield ME
The price is CA $200 per night from Jun 26 to Jun 27
CA $200
CA $442 total
Jun 26 - Jun 27
includes taxes & 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
The price is CA $155 per night from Jun 28 to Jun 29
CA $155
CA $169 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"a delay checking in. first room sink would not drain. second room load noises upstairs and dog barking down the hallway. they do not guarantee noise free rooms, no kidding. better rooms in this city. the attached food place is great."
Reviewed on Jun 24, 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.
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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.
