Pittsfield Vacation Packages

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Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,231, price is now CA $760 per person
CA $760
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $3,072, price is now CA $1,733 per person
CA $1,733
per person
Oct 10 - Oct 17
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
8.6/10 Excellent! (1,070 reviews)
The staff was friendly. Room was clean and met our needs. Expedia VIP allowed the resort fee to be waived which was wonderful.

Reviewed on Aug. 18, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,853, price is now CA $2,300 per person
CA $2,300
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,391, price is now CA $2,742 per person
CA $2,742
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
One of the nicest overall properties in the country

Reviewed on Aug. 20, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was CA $2,322, price is now CA $1,535 per person
CA $1,535
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul. 17, 2025

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Pittsfield Hotel Deals

The Centennial

The Centennial

4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Sep 1 to Sep 2
CA $152
CA $188 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (989 reviews)
"Great old exterior with modern interior"

Reviewed on Aug. 15, 2025

The Centennial
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Sep 7 to Sep 8
CA $111
CA $121 total
Sep 7 - Sep 8
includes taxes & fees
6.6/10 (694 reviews)
Winnisquam Inn
"The property is dated but clean. Staff was very friendly and helpful."

Reviewed on Aug. 12, 2025

Winnisquam Lake Inn
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 $158 per night from Sep 7 to Sep 8
CA $158
CA $171 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Great"

Reviewed on Aug. 21, 2025

Best Western Plus Landmark Inn
See all 1,147 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 $760 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.