Pittsfield Vacations from $273

Book a Hotel + Flight or Car together to unlock savings

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.
Howard Johnson by Wyndham Bangor

Howard Johnson by Wyndham Bangor

2 out of 5
Price was $366, price is now $273 per person
$273
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
14.8/10 Exceptional! (1,000 reviews)
Our stay at Howard Johnsons was great. They don't have a restaurant,so we had breakfast at Dennys. That was soso. The motel was clean and the service was good.

Reviewed on Nov 15, 2025

Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was $458, price is now $331 per person
$331
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
18.8/10 Exceptional! (2,448 reviews)
Front desk staff were very courteous and the room was perfect … keep up the great service

Reviewed on Nov 26, 2025

Black Bear Inn, an Ascend Collection Hotel

Black Bear Inn, an Ascend Collection Hotel

3 out of 5
Price was $383, price is now $288 per person
$288
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
18/10 Exceptional! (1,001 reviews)
Parking was fine. Breakfast left something to be desired.

Reviewed on Nov 23, 2025

The Lucerne Inn

The Lucerne Inn

3.5 out of 5
Lucerne-in-Maine
Price was $535, price is now $405 per person
$405
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
17.6/10 Exceptional! (1,001 reviews)
Everyone was very kind and welcoming!

Reviewed on Nov 18, 2025

Quality Inn at Bangor Mall

Quality Inn at Bangor Mall

2.5 out of 5
Price was $387, price is now $307 per person
$307
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Bangor (BGR)
16.4/10 Exceptional! (1,003 reviews)
As always, clean and welcoming!!

Reviewed on Nov 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pittsfield
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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

2 out of 5
Pittsfield Maine
$292 nightly
The price is $295 total per night from Nov 29 to Nov 30
$295 total
Nov 29 - Nov 30
Total with taxes and fees
Pine Tree Trail Lodge
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield ME
$283 nightly
The price is $309 total per night from Nov 30 to Dec 1
$309 total
Nov 30 - Dec 1
Total with taxes and 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

Angel Mist Retreat Garage Apartment
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $111 total per night from Dec 25 to Dec 26
$111 total
Dec 25 - Dec 26
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Room was clean and big. A little dated and the bathroom is small but that's ok. Staff was very nice and it was great having a full scale restaurant on site. Also, Walmart and a grocery store about a 3 minute walk away. Very convenient location right beside I-95.

Reviewed on Nov 20, 2025

Fireside Inn & Suites Waterville
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $273 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

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