Pittsfield Vacations from $643

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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.
Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
Price was $814, price is now $643 per person
$643
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Bangor (BGR)
7.8/10 Good! (1,001 reviews)
Overall stay was good

Reviewed on Aug 12, 2025

Historic 2 Cats Inn

Historic 2 Cats Inn

3 out of 5
Price was $1,734, price is now $1,386 per person
$1,386
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Bangor (BGR)
7.4/10 Good! (3 reviews)
The included breakfast was so good and highly recommended. There was an electrical outlet in the bathroom that didn’t work. Also, not sure if it was us, but we couldn’t get the door to lock. However, for the location, cleanliness. We would stay here again. I might recommend a bigger refrigerator since we did have leftovers and they didn’t always fit in the fridge.

Reviewed on Oct 14, 2024

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $854, price is now $689 per person
$689
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.8/10 Exceptional! (221 reviews)
Beautiful property close to everything. We hope to return another time!

Reviewed on Aug 25, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Price was $1,987, price is now $1,633 per person
$1,633
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
Price was $1,207, price is now $995 per person
$995
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
7.2/10 Good! (65 reviews)
Driveway is bumpy but the cabin was nice

Reviewed on Aug 24, 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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $147 total per night from Sep 1 to Sep 2
$147 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"It was a good place to stay before the long drive home."

Reviewed on Aug 24, 2025

Fireside Inn & Suites Waterville
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Aug 27 to Aug 28
$162 total
Aug 27 - Aug 28
Total with taxes and fees
8.4/10 Very Good! (461 reviews)
"Check in was super quick, room was clean, everything worked, and the bed was comfy. Didn't experience any issues, and it was very quiet outside. Staff was friendly during check in and check out."

Reviewed on Aug 23, 2025

The Elmwood
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
$135 nightly
The price is $147 total per night from Sep 4 to Sep 5
$147 total
Sep 4 - Sep 5
Total with taxes and fees
8.6/10 Excellent! (789 reviews)
"Muy a gusto en esta propiedad y muy buen desayuno volvería a quedarme ahí"

Reviewed on Aug 24, 2025

Holiday Inn Express & Suites Waterville - North by IHG
See all 240 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.

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $643 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.