Pittsfield Vacations from $178

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The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $298, price is now $178 per person
$178
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,173 reviews)
The room was really awesome! Perfect for my one night stay! I absolutely loved the windows in the room out looking the streets

Reviewed on Nov 6, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
Price was $714, price is now $401 per person
$401
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (2,117 reviews)
Clean room, friendly staff, full breakfast.

Reviewed on Nov 6, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,451, price is now $836 per person
$836
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
So what a hotel. A small issue was handled with disproportionate kindness! The ambiance is lively, the space is luxe, the team from bellhop to GM were all exceptional. Thank you all for my short stop with you

Reviewed on Nov 5, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,830 reviews)
Staff was very friendly and accommodating ,the rooms were very clean

Reviewed on Nov 6, 2025

The Bostonian Boston

The Bostonian Boston

4 out of 5
Government Center
Save 100% on your flight
Price was $653, price is now $406 per person
$406
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,952 reviews)
Staff is great. Room good size. Balcony has nice views

Reviewed on Nov 3, 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
$146 nightly
The price is $158 total per night from Nov 18 to Nov 19
$158 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Historic building very cool, beautiful rooms they’re all little different. I was in the turret room very reasonably priced.

Reviewed on Nov 2, 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
$85 nightly
The price is $92 total per night from Nov 9 to Nov 10
$92 total
Nov 9 - Nov 10
Total with taxes and fees
6.6/10 (797 reviews)
Everything is ok

Reviewed on Oct 27, 2025

Winnisquam Lake Inn
Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
515 South St, Bow, NH
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $95 total per night from Dec 7 to Dec 8
$95 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
amazing

Reviewed on Nov 3, 2025

Hampton Inn by Hilton Concord/Bow
See all 1,149 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.

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 $178 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.