Pittsfield Vacations from ￥83,170

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Pittsfield Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.6/10 Exceptional! (2,990 reviews)
Be mindful of what time you are checking in, it can get busy. Other than that it’s EXCELLENT!

Reviewed on Jun 19, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Location for first time Boston visitors was really good as a lot area to explore by foot then you could Uber the rest. The staff and in-room dining was outstanding

Reviewed on Jun 16, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Had dinner at the restaurant unfortunately it was the greatest food. The salmon was grilled and was dry and over cooked. I also had fries that were over cooked. Not what I’d expect for a hotel and restaurant of this standard.

Reviewed on Jun 16, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
9.4/10 Exceptional! (347 reviews)
The staff were very helpful. The hotel is exceptionally clean and well appointed.

Reviewed on Jun 6, 2025

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
per person
Jul 21 - Jul 24
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
8.6/10 Excellent! (1,588 reviews)
Beautiful view. Good location

Reviewed on Jun 16, 2025

Find the Best Pittsfield Vacation Packages

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 ￥15,899 per night from Jun 29 to Jun 30
￥15,899
￥17,250 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Ok hotel but does need some upgrades. They were redoing the pool area."

Reviewed on Jun 13, 2025

Comfort Inn Concord
TownePlace Suites by Marriott Gilford
TownePlace Suites by Marriott Gilford
3 out of 5
14 Sawmill Road, Gilford, NH
The price is ￥22,114 per night from Jun 22 to Jun 23
￥22,114
￥23,994 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (528 reviews)
"Great place to stay!"

Reviewed on Jun 12, 2025

TownePlace Suites by Marriott Gilford
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 ￥16,517 per night from Jun 22 to Jun 23
￥16,517
￥17,921 total
Jun 22 - Jun 23
includes taxes & fees
7.6/10 Good! (1,009 reviews)
"Was conveniently located to the Bank of New Hampshire Pavillion. Nice place stay after the convert. Comfy beds."

Reviewed on Jun 16, 2025

Best Western Plus Landmark Inn
See all 1,136 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.

Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from ￥83,170 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.