Pittsfield Vacations from $386

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was $590, price is now $386 per person
$386
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Great room, wonderful friendly customer service

Reviewed on Feb 8, 2026

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $729, price is now $453 per person
$453
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Quiet, clean and comfortable. Extremely responsive staff with caring, kind, respectful interactions and communication. Would definitely stay again.

Reviewed on Feb 9, 2026

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $805, price is now $514 per person
$514
per person
Mar 23 - Mar 29
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Great clean room that was nice and warm on the cold day. Loved the fireplace in the living area and the bed was very comfortable and cozy. Great value for the space we got!

Reviewed on Feb 8, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,045, price is now $695 per person
$695
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (4,672 reviews)
Everything: location, staff, room, (history too), just in general an unforgettable experience. THANK YOU. P.S. The only little "problem" is nuisance noise coming from the subway station just beneath the hotel. But we were laughing listening to metro trains departing as if they were airplanes taking off from Logan.

Reviewed on Feb 10, 2026

Found Hotel Boston Common

Found Hotel Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $665, price is now $447 per person
$447
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.2/10 Very Good! (1,253 reviews)
Heat didn't work and

Reviewed on Feb 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Pittsfield
View all trips

Pittsfield Hotel Deals

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2 out of 5
76 Mountain Rd Epsom NH
$159 nightly
The price is $173 total per night from Feb 11 to Feb 12
$173 total
Feb 11 - Feb 12
Total with taxes and fees
9.6/10 Exceptional! (116 reviews)
Good

Reviewed on Feb 7, 2026

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
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
$106 nightly
The price is $115 total per night from Feb 22 to Feb 23
$115 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
The room was ver y nice, clean and comfortable. Check in staff were friendly and helpful.

Reviewed on Feb 5, 2026

Hampton Inn by Hilton Concord/Bow
Comfort Inn Concord South End

Comfort Inn Concord South End

2.5 out of 5
71 Hall St Concord NH
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $125 total per night from Mar 11 to Mar 12
$125 total
Mar 11 - Mar 12
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
things were just as they should be

Reviewed on Jan 25, 2026

Comfort Inn Concord South End
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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $386 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.