Pittsfield Vacations from $498

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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.
The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $589, price is now $498 per person
$498
per person
Apr 29 - May 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Bangor (BGR)
9.8/10 Exceptional! (332 reviews)
Staff was super nice and helpful. Cookies were delicious! The room was very clean and the bed was super comfortable. Breakfast is in the attached restaurant, not buffet style. Would absolutely stay here again!

Reviewed on Mar 1, 2026

Hollywood Casino Bangor

Hollywood Casino Bangor

3 out of 5
Price was $765, price is now $651 per person
$651
per person
May 7 - May 10
found 12 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Bangor (BGR)
8.6/10 Excellent! (1,375 reviews)
The rooms were very clean and the staff were great!

Reviewed on Feb 23, 2026

Hotel Ursa

Hotel Ursa

4 out of 5
Price was $814, price is now $698 per person
$698
per person
May 28 - Jun 1
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.6/10 Exceptional! (626 reviews)
Great place to stay on campus

Reviewed on Mar 3, 2026

The Lucerne Inn

The Lucerne Inn

3.5 out of 5
Lucerne-in-Maine
Price was $800, price is now $717 per person
$717
per person
May 28 - Jun 1
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.8/10 Excellent! (1,001 reviews)
The staff was great and friendly and helpful. Our room was upgraded and when we were in dining room for dinner it was a bit chilly sitting next to the windows and manager brought over a heater and put beside me. The meal was excellent.

Reviewed on Dec 28, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was $747, price is now $672 per person
$672
per person
May 28 - Jun 1
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.4/10 Exceptional! (2,408 reviews)
I should have made a reservation through the Hotel itself it would have been cheaper.

Reviewed on Mar 2, 2026

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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

Pine Tree Trail Lodge

Pine Tree Trail Lodge

3 out of 5
129 Morrill St Pittsfield ME
Get rates
Pine Tree Trail Lodge
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
$94 nightly
The price is $102 total per night from Mar 8 to Mar 9
$102 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (881 reviews)
Clean room in very good condition, friendly staff, great breakfast. Hallways and stairwells need a refresher. Parking is okay.

Reviewed on Mar 1, 2026

Holiday Inn Express & Suites Waterville - North by IHG
Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

3 out of 5
375 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $104 total per night from Mar 5 to Mar 6
$104 total
Mar 5 - Mar 6
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
Bathtub was not clean - Bed seemed to be old and very uncomfortable with dips in it. The woman doing check in was not a very pleasant person didn't even make eye contact or ask about stay. I am happy we only were staying 1 night.

Reviewed on Mar 1, 2026

Best Western Plus Waterville Grand Hotel
See all 239 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 $498 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.