Pittsfield Vacation Packages

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Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Mar. 9 - Mar. 12
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
8.6/10 Excellent! (1,002 reviews)
The Copley is old school Boston. The hotel has lots of character and is located in one of the nicest parts of the city Back Bay.

Reviewed on Dec. 22, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Feb. 16 - Feb. 21
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Terrific staff! Concierge, door men, wait staff, room cleanliness, just excellent. Really can’t wait to come back. RA McCall

Reviewed on Dec. 19, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 16 - Feb. 21
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (83 reviews)
V nice room deco and designs. Attentive staff who are in close touch via text. Great experience all around.

Reviewed on Nov. 29, 2024

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Mar. 9 - Mar. 12
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
Beautiful hotel with amazing staff! My family had a wonderful time!

Reviewed on Dec. 16, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Feb. 9 - Feb. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (313 reviews)
It’s definitely a cut above standard hotels.

Reviewed on Dec. 15, 2024

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Pittsfield Hotel Deals

Comfort Inn Concord
Comfort Inn Concord
2.5 out of 5
71 Hall St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Jan. 19 to Jan. 20
CA $142
CA $154 total
includes taxes & fees
Jan 19 - Jan 20, 2025
8.2/10 Very Good! (1,006 reviews)
"We liked the nice environment and well mantein hotel . We comeback every year. We are family. The breakfast is nice. The staff super kind. We have positive experience."

Reviewed on Dec. 23, 2024

Comfort Inn Concord
The Centennial
The Centennial
4 out of 5
96 Pleasant St, Concord, NH
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Dec. 29 to Dec. 30
CA $167
CA $205 total
includes taxes & fees
Dec 29 - Dec 30
8.8/10 Excellent! (869 reviews)
"Good stay. Nice room in quiet corner."

Reviewed on Dec. 23, 2024

The Centennial
Steele Hill Resorts
Steele Hill Resorts
3 out of 5
516 Steele Hill Road, Sanbornton, NH
The price is CA $266 per night from Jan. 2 to Jan. 3
CA $266
CA $288 total
includes taxes & fees
Jan 2 - Jan 3, 2025
8.2/10 Very Good! (580 reviews)
"Great"

Reviewed on Dec. 3, 2024

Steele Hill Resorts
See all 1,052 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?
You’ll find cheap prices from CA $733 on Expedia for your Pittsfield escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
The off-season is the best time to travel to Pittsfield if you’re trying to save. Another tip for scoring cheap Pittsfield vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Pittsfield?
The ideal length of your Pittsfield vacation depends on what you’d like to do. Typically, a handful of days to a week will give you enough time to check out all the major attractions and discover some hidden spots along the way.
How to find the best Pittsfield package deals?
Use Expedia’s filters to find some tempting Pittsfield package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even better 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 save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can customize your Pittsfield escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pittsfield?
Land amazing discounts by reserving 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 adventure.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your diary and pack your bags. Your favorite season and the type of activities available will also help you decide when to visit Pittsfield.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Pittsfield.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you’d like to get to in Pittsfield. Then, estimate how long you’ll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, 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.