Pittsfield Vacations from $876
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The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Boston
Bay Village
$2,036
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Lexington Green Historic District
$1,099
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Boston (BOS)
9.6/10 Exceptional! (266 reviews)
I had a King room with a fireplace, it was a nice size room and very clean. The bathroom was nice and they had a robe hanging for me. Little touches like personalized notes and soft drinks in the refrigerator and snacks to pick up for the room. The staff was very friendly. I'm not a breakfast eater so can't really comment on that although there was a nice continental spread and you could order off the menu. I will say that I was a bit disappointed in the restaurant. Had dinner there the night before and for the price, I felt the food was a little lackluster. The bartender was very nice and he was my server as well. All in all I really enjoyed my stay and if I go back to Lexington I would stay there again.
Reviewed on Sep 4, 2026
Stay near popular Pittsfield attractions
Harold Conrad Square
This quaint community park in Pittsfield offers a peaceful retreat for quiet reflection and leisurely walks. Bring a picnic lunch and explore the historic churches nearby for a charming small-town experience.
Scenic Theatre
The Scenic Theatre showcases local talent through vibrant community productions in historic Pittsfield. Catch an intimate evening performance of classic plays or contemporary musicals in this charming cultural hub.
Drake Field
Drake Field hosts the colorful annual Rotary Balloon Festival, a highlight of Pittsfield's summer. Stroll the riverside trail or relax in the gazebo while watching hot air balloons fill the August sky.
Josiah Carpenter Library
This 1901 neoclassical library designed by Butterfield serves as Pittsfield's community learning hub. Browse the collection while admiring the historical architecture that creates a charming, quiet atmosphere.
Pittsfield Hotel Deals
The Centennial
96 Pleasant St Concord NH
Fully refundableReserve now, pay when you stay
$136 nightly
$147 total
Nov 4 - Nov 5
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"This was a very nice hotel. The only complaint would be the elevator was not working. Location was excellent, close to restaurants in walking distance."
Reviewed on Oct 8, 2026
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
$175 nightly
$190 total
Nov 9 - Nov 10
Total with taxes and fees
9.6/10 Exceptional! (225 reviews)
"Oh my gosh I can’t say enough positive things about this place (staff mostly) My fiancé and I stayed here a few weeks ago and I booked it for his birthday. I was messaging the staff ahead of time and they actually asked what his name was so they could write a card. When we walked in there was a hand ..."
Reviewed on Oct 8, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$101 nightly
$110 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Pittsfield Vacation Packages
Pittsfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Population | 1,600 |
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Frequently asked questions
How much does a Pittsfield vacation package cost?
You'll find cheap prices from $876 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?
You can generally find lower rates and better availability in November, December and January. Explore our cheap Pittsfield vacation packages and you could land some great off-season deals.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to tick off the main sights during your Pittsfield vacation. However, if you'd like to have more time to relax or go on day tours, think about extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Set off on your perfect trip to Pittsfield with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.