Pittsfield Vacations from $257

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Your Pittsfield Vacation

Say bye-bye to planning hassles and hello to a Pittsfield vacation package. With your travel details organized before you take off, you can focus on discovering this city, starting with Main Street, which is great for bars and pubs, culture and dining. You'll want to do some exploring during your trip to Pittsfield. Don't miss major attractions such as University of Michigan, Michigan Stadium and University of Michigan Museum of Art. Browse Expedia's wide range of travel options and start organizing your dream vacation to Pittsfield today.

The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
American Inn & Suites Waterford

American Inn & Suites Waterford

3 out of 5
Price was $414, price is now $257 per person
$257
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
5.6/10 (1,001 reviews)
Amanda at the desk was amazing. So friendly and helpful. Thank you Amanda!!

Reviewed on Dec 7, 2025

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $770, price is now $443 per person
$443
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,004 reviews)
I had an amazing stay here! I didn’t have much time to fully explore but everyone was super nice and food was great! Loved the style and aesthetic and the rooms were comfortable. My only complaint is my room could have been cleaner there was a stain in my bedding and things missing like coffee and smaller stuff. I’d definitely come back in the summer!

Reviewed on Jan 14, 2026

Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Price was $829, price is now $542 per person
$542
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (1,002 reviews)
This place is underrated. We’ve stayed here probably a dozen times and never had an issue. The location is great and parking is easy and cheap.

Reviewed on Jan 16, 2026

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Discover the most popular places to visit in Pittsfield

University of Michigan as well as a couple

University of Michigan

4.5/5(1,101 reviews)

Come to see the ivied halls, grassy quads, cultural performances and athletic events at this renowned university, one of the world’s most prestigious.

University of Michigan
Michigan Football.

Michigan Stadium

4.5/5(445 reviews)

Catch an event at Michigan Stadium during your trip to Ann Arbor. Experience the area's lively festivals or attend a sporting event.

Michigan Stadium
Hill Auditorium showing heritage elements

Hill Auditorium

4.5/5(54 reviews)

Enjoy classical music, a rock concert or performing arts event in this impressive century-old venue on the University of Michigan campus.

Hill Auditorium

Pittsfield Hotel Deals

Ann Arbor Regent Hotel & Suites

Ann Arbor Regent Hotel & Suites

3 out of 5
2455 Carpenter Road Ann Arbor MI
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $127 total per night from Jan 19 to Jan 20
$127 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (1,316 reviews)
Room was very clean, i left the room clean, stripped the sheets and put wet towels in the tub

Reviewed on Jan 11, 2026

Ann Arbor Regent Hotel & Suites
Days Inn by Wyndham Ann Arbor

Days Inn by Wyndham Ann Arbor

2 out of 5
2380 Carpenter Road Ann Arbor MI
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $68 total per night from Jan 28 to Jan 29
$68 total
Jan 28 - Jan 29
Total with taxes and fees
4.6/10 (1,000 reviews)
Room was all good!

Reviewed on Jan 6, 2026

Days Inn by Wyndham Ann Arbor
La Quinta Inn & Suites by Wyndham Detroit Metro Airport

La Quinta Inn & Suites by Wyndham Detroit Metro Airport

3 out of 5
30847 Flynn Drive Romulus MI
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from Feb 1 to Feb 2
$96 total
Feb 1 - Feb 2
Total with taxes and fees
8.2/10 Very Good! (2,254 reviews)
We stayed here because of its proximity to DTW. The room was clean and fresh. Lots of pillows on the bed. Bathroom was in excellent shape. If you're looking for a clean, quiet room at a reasonable price, this is a good choice.

Reviewed on Jan 15, 2026

La Quinta Inn & Suites by Wyndham Detroit Metro Airport
See all 830 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
Detroit Metropolitan Wayne County Airport (DTW)
Top Sights
University of Michigan Museum of Art, Ann Arbor Hands On Museum and Exhibit Museum of Natural History at the University Of Michigan

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $257 on Expedia for your Pittsfield getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
October, November and December are the best times to search for cheap Pittsfield vacation packages. Choosing to travel in less busy periods means you can usually find better prices on hotels and flights.
How many days is enough for Pittsfield?
You can visit all the major sights in Pittsfield within a few days, including the must-see Briarwood Mall. If you're after a longer Pittsfield vacation, check out which kind of day trips and activities are available in the area.
How to find the best Pittsfield package deals?
Begin your search for a Pittsfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Pittsfield package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pittsfield escape underway.
Is it cheaper to book a Pittsfield vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Pittsfield vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pittsfield?
If you're considering an impromptu Pittsfield adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Set off on your dream getaway to Pittsfield with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel 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.