Pittsfield Vacations from $777

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Country Inn at The Mall

Country Inn at The Mall

2 out of 5
Price was $906, price is now $777 per person
$777
per person
Jul 3 - Jul 7
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.4/10 Exceptional! (2,389 reviews)
Good breakfast. Pleasant experience

Reviewed on Apr 28, 2026

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Price was $1,614, price is now $1,260 per person
$1,260
per person
Jul 10 - Jul 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Bangor (BGR)
8.6/10 Excellent! (246 reviews)
The staff is wonderful, it’s convenient to bar harbor but away from the crowds, rooms are charming and very maine.! We will absolutely stay here sharing, wonderful, priced right and charming!

Reviewed on Oct 26, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
Price was $3,116, price is now $2,575 per person
$2,575
per person
Jul 3 - Jul 7
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $1,824, price is now $1,555 per person
$1,555
per person
Jul 10 - Jul 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Bangor (BGR)
9.8/10 Exceptional! (424 reviews)
We really enjoyed staying at the pathmaker, the staff were really friendly and kind. Will definitely be staying here if we return to bar harbor

Reviewed on Apr 28, 2026

Moseley Cottage Inn & Town Motel

Moseley Cottage Inn & Town Motel

3 out of 5
Downtown Bar Harbor
Price was $1,664, price is now $1,425 per person
$1,425
per person
Jul 10 - Jul 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Bangor (BGR)
9.4/10 Exceptional! (560 reviews)
Great value for location. Clean rooms, easy check in/out.

Reviewed on Oct 30, 2025

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

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, Book Swap

The Cozy Home- New, Comfortable, Book Swap

Pittsfield ME
$209 nightly
The price is $228 total per night from Apr 30 to May 1
$228 total
Apr 30 - May 1
Total with taxes and fees
10/10 Exceptional! (1 review)
Great host great stay

Reviewed on Nov 24, 2025

The Cozy Home- New, Comfortable, Book Swap
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 May 3 to May 4
$105 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (905 reviews)
Very clean, well kept and stylish facility. Room was spacious and well thought through in design. Very comfortable. Staff was also excellent. Welcoming and accommodating. Also has an exercise room and indoor pool for customers.

Reviewed on Apr 22, 2026

Holiday Inn Express & Suites Waterville - North by IHG
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $117 total per night from May 3 to May 4
$117 total
May 3 - May 4
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Very nice property to stay. Close to hospital and amenities.

Reviewed on Apr 25, 2026

Fireside Inn & Suites Waterville
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

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 $777 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.