Pittsfield Vacation Packages

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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!

Top Pittsfield Vacation Deals

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 CA $1,253, price is now CA $1,119 per person
CA $1,119
per person
Oct 5 - Oct 10
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
7.4/10 Good! (1,004 reviews)
Was quiet for the area it is in. Clean rooms. Safe area.

Reviewed on Aug. 17, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Price was CA $2,603, price is now CA $2,222 per person
CA $2,222
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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

Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
Price was CA $1,451, price is now CA $1,244 per person
CA $1,244
per person
Oct 5 - Oct 10
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
7.8/10 Good! (1,001 reviews)
Overall stay was good

Reviewed on Aug. 12, 2025

Acadia Pines Motel

Acadia Pines Motel

2.5 out of 5
Price was CA $1,715, price is now CA $1,509 per person
CA $1,509
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Bangor (BGR)
7.2/10 Good! (270 reviews)
This motel is conveniently located near restaurants, mini golf, ocean access. It is clean and the staff is pleasant. It is very close to road on route 3, the main thorough fare between MDI, Bar Harbor, and the mainland. Unfortunately, it is getting shabby and rundown.

Reviewed on Aug. 12, 2025

Hampton Inn Bangor

Hampton Inn Bangor

2.5 out of 5
Price was CA $1,507, price is now CA $1,367 per person
CA $1,367
per person
Oct 5 - Oct 10
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bangor (BGR)
9.2/10 Wonderful! (1,012 reviews)
Pretty basic, but nice stay.

Reviewed on Aug. 22, 2025

Ready to book your vacation to Pittsfield?

 

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Pittsfield Hotel Deals

Family, Friends and Fun for all

Family, Friends and Fun for all

2 out of 5
Pittsfield
The price is CA $191 per night from Aug 24 to Aug 25
CA $191
CA $541 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (2 reviews)
"The property was very nice. Lots of rooms, fun environment, prompt communication. Worked great for our group."

Reviewed on Aug. 17, 2025

Family, Friends and Fun for all
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 24 to Aug 25
CA $202
CA $220 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"We enjoyed our stay & we will be back"

Reviewed on Aug. 22, 2025

Fireside Inn & Suites Waterville
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Aug 24 to Aug 25
CA $206
CA $225 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (457 reviews)
"Amanda at check in was fantastic! Room recently refurbished, clean, and comfortable."

Reviewed on Aug. 16, 2025

The Elmwood
See all 240 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Pittsfield vacation package cost?
Offering excellent value package deals from CA $1,119 on Expedia, you'll be thrilled with how little a vacation to Pittsfield costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pittsfield?
To pick up cheap Pittsfield vacation packages, organize your trip outside of busy periods such as public holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to see the major sights during your Pittsfield vacation. But if you'd like to have some time to relax or take day tours, consider extending your trip.
How to find the best Pittsfield package deals?
Use Expedia's filter tool to help you find some fabulous Pittsfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights separately. Better still, you can personalize your Pittsfield trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pittsfield?
Secure incredible bargains by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Pittsfield trip.
How to plan a trip to Pittsfield?

  1. Choose when to travel: Check your calendar and get packing. Your favourite season and the activities on offer will also help you decide when to vacation in Pittsfield.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to put aside for your trip to Pittsfield. Then, select a property that matches your budget, whether that's an affordable option or a deluxe getaway.
  3. Work out your trip length: Think about how long you'd like to spend discovering Pittsfield. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Pittsfield vacation package.

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