Pittsfield Vacations from $281

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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 Inn on Mount Desert

The Inn on Mount Desert

3 out of 5
Price was $350, price is now $281 per person
$281
per person
Dec 12 - Dec 14
found 23 hours ago
Roundtrip flight included
New York (NYC) to Bangor (BGR)
9.6/10 Exceptional! (1,005 reviews)
Excellent inn with many rooms but didn’t feel crowded even at breakfast in the indoor/outdoor spaces. Free private parking and walkable in town. Cute garden and gas fire pit outside also with outdoor rocking chairs on the front porch, and a side area for eating or resting outside. Breakfast was good and included a savory or a sweet option and fresh fruit. Pastries, bread, cereal, and other accoutrements were available for supplement. Rooms were very nice with good beds and bedding and had a microwave and mini fringe and small counter area.

Reviewed on Oct 9, 2025

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $404, price is now $288 per person
$288
per person
Dec 12 - Dec 14
found 23 hours ago
Roundtrip flight included
New York (NYC) to Bangor (BGR)
9.8/10 Exceptional! (248 reviews)
The property was convenient to shopping and dining. The breakfast was wonderful and included in the cost which was an added bonus. The room was clean and comfortable.

Reviewed on Oct 7, 2025

Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
Price was $445, price is now $355 per person
$355
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Bangor (BGR)
7.8/10 Good! (1,007 reviews)
Comfortable bed, soft bedding

Reviewed on Oct 10, 2025

The Primrose

The Primrose

3 out of 5
Price was $406, price is now $326 per person
$326
per person
Dec 12 - Dec 14
found 23 hours ago
Roundtrip flight included
New York (NYC) to Bangor (BGR)
9.6/10 Exceptional! (937 reviews)
Breakfast was fantastic

Reviewed on Sep 27, 2025

Hearthside Inn

Hearthside Inn

2.5 out of 5
Price was $511, price is now $412 per person
$412
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Bangor (BGR)
9.8/10 Exceptional! (190 reviews)
Really delightful! Staff was so friendly, rooms were very cozy. I loved breakfast and afternoon tea, there was always a snack to be found.

Reviewed on Sep 27, 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

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
$270 nightly
The price is $295 total per night from Oct 12 to Oct 13
$295 total
Oct 12 - Oct 13
Total with taxes and fees
10/10 Exceptional! (13 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
$112 nightly
The price is $122 total per night from Oct 31 to Nov 1
$122 total
Oct 31 - Nov 1
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Very clean."

Reviewed on Oct 6, 2025

Fireside Inn & Suites Waterville
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
$111 nightly
The price is $121 total per night from Nov 9 to Nov 10
$121 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (825 reviews)
"Friendly and courteous staff. Very helpful with dining locations. Would recommend a lounge/pub setting to enjoy a drink after a long traveling day. Excellent hotel!!!"

Reviewed on Oct 6, 2025

Holiday Inn Express & Suites Waterville - North by IHG
See all 233 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.

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 $281 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.