Pittsfield Vacations from $1,172

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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
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.8/10 Exceptional! (206 reviews)
The woman that checked us in was so sweet (give her a raise) and the rooms are lovely

Reviewed on Aug 16, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
7.4/10 Good! (3 reviews)
Loved the charm, cleanliness, decor and location. However, internet was so bad we couldn’t watch more than a few seconds of YouTube at a time. Upstairs shower had the lowest flow we’ve ever seen, even with volume turned up to maximum. Dishwasher was commercial and required many manual steps lifting basket, etc and special soap that we never found. Easier to hand wash. No laundry and outdoor light didn’t work at night so we stepped in dog pooh getting out of the car when we arrived. Beautiful little place that needs some attention.

Reviewed on Oct 11, 2023

Bar Harbor Main Street Apartments

Bar Harbor Main Street Apartments

3.5 out of 5
Downtown Bar Harbor
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.2/10 Wonderful! (5 reviews)
Very clean, modern space. Property owner was very informative and gave perfect instructions for check in/out. Apt was in great location, at end of village, in quiet area of town, but within walking distance to everything, no need to drive for Village activities. Included all necessities. Only upgrade I would suggest would be to add a full length mirror in the bedrooms or somewhere in apt. Otherwise, no complaints! Would definitely recommend and stay again!!

Reviewed on Jul 29, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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

Downtown Apartments in Bar Harbor

Downtown Apartments in Bar Harbor

3 out of 5
Downtown Bar Harbor
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bangor (BGR)
9.2/10 Wonderful! (9 reviews)
Super convenient to the main street of shopping. Nice apartment.

Reviewed on Jul 17, 2024

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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

Family, Friends and Fun for all

Family, Friends and Fun for all

2 out of 5
Pittsfield
$357 nightly
The price is $389 total per night from Aug 24 to Aug 25
$389 total
Aug 24 - Aug 25
Total includes taxes and fees
Great stay, would stay again
"The house was as described, plenty of space for the whole family, we had a stay of 9 with no issues. Property owner was onsite and awaiting our arrival, l can't say that's a normal thing, but was very helpful in learning our way around the property. The location was great for us, the drive to the ..."

Reviewed on Jul 30, 2025

Family, Friends and Fun for all
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
$284 nightly
The price is $310 total per night from Aug 25 to Aug 26
$310 total
Aug 25 - Aug 26
Total includes taxes and fees
10/10 Exceptional! (10 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."

Reviewed on Jul 23, 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
$149 nightly
The price is $162 total per night from Aug 31 to Sep 1
$162 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Attached to the hotel is the Governor's restaurant (the pictures that show bakery items under glass). Pool and hot tub are well maintained, I see maintenance and staff all around the property from early hours until late. Grab and Go breakfast choices on par with many breakfast options from most hotel ..."

Reviewed on Aug 13, 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.

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $1,172 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.