Pittsfield Vacation Packages

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Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

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Pittsfield Hotel Deals

Best Western Plus Landmark Inn
Best Western Plus Landmark Inn
2.5 out of 5
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Jul 16 to Jul 17
CA $156
CA $169 total
Jul 16 - Jul 17
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Overall, we were happy with our stay. Our room and the property itself was clean. Aside from the person who checked us in every other person we interacted with for staff was great. Person who checked us in didn’t even acknowledge us with the hello or a smile, simply said license and credit card when ..."

Reviewed on Jul. 11, 2025

Best Western Plus Landmark Inn
Microtel Inn & Suites by Wyndham Dover
Microtel Inn & Suites by Wyndham Dover
2 out of 5
31 Webb Pl, Dover, NH
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Aug 4 to Aug 5
CA $163
CA $177 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (999 reviews)
"The hotel is fine except the room felt a little outdated. It was all kn good condition and clean, but it did not feel as up-to-date as some other chain hotel rooms. The bed was not overly comfortable, and all the mirrors made it a little cheesy, especially the ones around the jacuzzi. It was nice ..."

Reviewed on Jul. 6, 2025

Microtel Inn & Suites by Wyndham Dover
Tilton Lodge Inn and Suites
Tilton Lodge Inn and Suites
2.5 out of 5
650 laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 21 to Jul 22
CA $122
CA $132 total
Jul 21 - Jul 22
includes taxes & fees
5.4/10 (35 reviews)
Wouldn't stay there again
"Building as whole was extremely run down and deteriorated. Property wasn't well maintained. Hallways weren't dirty and didn't smell pleasant. Room it self was fine. Decently clean and obviously remodled compared to the rest ofnthe building/property."

Reviewed on Jul. 9, 2025

Tilton Lodge Inn and Suites
See all 1,163 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.

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Frequently asked questions

How much does a Pittsfield vacation package cost?
Offering great value package deals from CA $705 on Expedia, you'll be thrilled with how little a vacation to Pittsfield costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pittsfield?
Travel in the off-season and you're likely to get cheap Pittsfield vacation packages. Keep in mind that school vacation periods and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Pittsfield?
With a well-organized travel plan, you can easily tick off the most popular Pittsfield sights in a handful of days. But if you'd like to explore off the beaten track or go on day trips, consider booking your Pittsfield vacation for longer.
How to find the best Pittsfield package deals?
Begin your search for a Pittsfield package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Pittsfield package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pittsfield escape off to a flying start.
Is it cheaper to book a Pittsfield vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can customize your Pittsfield escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Pittsfield?
Enjoy incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pittsfield vacation.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to vacation in Pittsfield.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodations will probably be the largest expense during your trip to Pittsfield.
  3. Work out your trip length: Consider how long you'd like to spend discovering Pittsfield. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: Once you've settled on your travel dates and duration, book the right Pittsfield vacation package for you.

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