Pittsfield Vacations from $779

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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.
Hotel Ursa

Hotel Ursa

4 out of 5
Price was $1,073, price is now $779 per person
$779
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.6/10 Exceptional! (676 reviews)
Great color scheme and comfortable beds.

Reviewed on May 4, 2026

Acadia Pines Motel

Acadia Pines Motel

2.5 out of 5
Save 100% on your flight
Price was $1,407, price is now $944 per person
$944
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
7.4/10 Good! (286 reviews)
Good value. Refrigerator and Microwave in room. Comfortable outdoor seating.

Reviewed on Oct 5, 2025

Mount Battie Inn

Mount Battie Inn

2.5 out of 5
Price was $1,330, price is now $1,022 per person
$1,022
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.8/10 Excellent! (323 reviews)
The room was very nice and comfortable and was a real convenient location for us. The area is gorgeous and owners were absolutely wonderful and kind.

Reviewed on Oct 19, 2025

Anchorage Motel

Anchorage Motel

2.5 out of 5
Price was $1,511, price is now $1,173 per person
$1,173
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9/10 Wonderful! (1,002 reviews)
The building was definitely older but the bed was very comfy and the

Reviewed on May 1, 2026

High Tide Inn

High Tide Inn

2 out of 5
Price was $1,259, price is now $981 per person
$981
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9/10 Wonderful! (317 reviews)
Super friendly staff.

Reviewed on Oct 26, 2025

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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.

JW Parks Golf Course

Pittsfield Hotel Deals

The Cozy Home- New, Comfortable, Book Swap

The Cozy Home- New, Comfortable, Book Swap

Pittsfield ME
$216 nightly
The price is $235 total per night from May 16 to May 17
$235 total
May 16 - May 17
Total with taxes and fees
10/10 Exceptional! (1 review)
Great host great stay

Reviewed on Nov 24, 2025

The Cozy Home- New, Comfortable, Book Swap
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St Waterville ME
Fully refundable
$100 nightly
The price is $109 total per night from May 10 to May 11
$109 total
May 10 - May 11
Total with taxes and fees
8.6/10 Excellent! (912 reviews)
Stayed over for work. Did not use amenities or have breakfast. A couple of the other guys did said it was good.

Reviewed on May 5, 2026

Holiday Inn Express & Suites Waterville - North by IHG
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $118 total per night from May 10 to May 11
$118 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Very nice property to stay. Close to hospital and amenities.

Reviewed on Apr 25, 2026

Fireside Inn & Suites Waterville
See all 259 properties in Pittsfield
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 $779 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.