Pittsfield Vacations from $707

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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.
Hollywood Casino Bangor

Hollywood Casino Bangor

3 out of 5
Price was $833, price is now $707 per person
$707
per person
Jun 29 - Jul 2
found 1 day ago
Roundtrip flight included
New York (JFK) to Bangor (BGR)
8.6/10 Excellent! (1,390 reviews)
Every time I stay in Bangor, this is my first choice. Staff is amazing, hotel is clean, the restaurants are also really great.

Reviewed on Apr 11, 2026

Moseley Cottage Inn & Town Motel

Moseley Cottage Inn & Town Motel

3 out of 5
Downtown Bar Harbor
Price was $1,353, price is now $1,080 per person
$1,080
per person
Jun 20 - Jun 24
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Bangor (BGR)
9.4/10 Exceptional! (560 reviews)
Great value for location. Clean rooms, easy check in/out.

Reviewed on Oct 30, 2025

Historic 2 Cats Inn

Historic 2 Cats Inn

3 out of 5
Price was $2,026, price is now $1,619 per person
$1,619
per person
Jul 2 - Jul 6
found 20 hours ago
Roundtrip flight included
New York (NYC) to Bangor (BGR)
8.4/10 Very Good! (5 reviews)
Staff was excellent both the Inn and the Restaurant. Responsive to our messages and very helpful. Can’t wait to go back in the future.

Reviewed on Sep 30, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Price was $2,409, price is now $2,022 per person
$2,022
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Bangor (BGR)
8/10 Very Good! (4 reviews)
It was beautiful inside and out. Would recommend 10/10. Very quiet location beds slept great and close to Bar Harbor

Reviewed on Sep 30, 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, Centrally located

The Cozy Home- New, Comfortable, Centrally located

Pittsfield ME
$211 nightly
The price is $230 total per night from Apr 14 to Apr 15
$230 total
Apr 14 - Apr 15
Total with taxes and fees
10/10 Exceptional! (1 review)
Great host great stay

Reviewed on Nov 24, 2025

The Cozy Home- New, Comfortable, Centrally located
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
$96 nightly
The price is $105 total per night from Apr 26 to Apr 27
$105 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (895 reviews)
Nice

Reviewed on Apr 8, 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
$114 nightly
The price is $124 total per night from Apr 15 to Apr 16
$124 total
Apr 15 - Apr 16
Total with taxes and fees
7.6/10 Good! (1,014 reviews)
Excellent

Reviewed on Apr 11, 2026

Best Western Plus Waterville Grand Hotel
See all 251 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 $707 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.