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.
Acadia Pines Motel

Acadia Pines Motel

2.5 out of 5
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Bangor (BGR)
7.2/10 Good! (258 reviews)
Was located perfectly for our plans!

Reviewed on Jul. 28, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Calgary (YYC) 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

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Bangor (BGR)
8.6/10 Excellent! (209 reviews)
Clean, so adorable inside. The property is excellent.

Reviewed on Aug. 2, 2025

Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Bangor (BGR)
7.2/10 Good! (61 reviews)
The cabins certainly need updating, however it was clean. The bed was comfortable and the sheets were nice.

Reviewed on Jul. 7, 2025

Cozy 2 BR by River- Crooked Steeple Hall

Cozy 2 BR by River- Crooked Steeple Hall

4 out of 5
per person
Oct 3 - Oct 6
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Bangor (BGR)
No reviews

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 $189 per night from Aug 5 to Aug 6
CA $189
CA $536 total
Aug 5 - Aug 6
includes taxes & fees
Family, Friends and Fun for all
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
The price is CA $194 per night from Aug 6 to Aug 7
CA $194
CA $427 total
Aug 6 - Aug 7
includes taxes & 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
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
The price is CA $186 per night from Aug 10 to Aug 11
CA $186
CA $203 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (774 reviews)
"Staff was very friendly. The room was very spacious and very clean."

Reviewed on Aug. 1, 2025

Holiday Inn Express & Suites Waterville - North by IHG
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
Offering excellent value package deals from CA $1,570 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.