Pittsfield Vacations from $338

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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.
Saint John's Resort

Saint John's Resort

4 out of 5
Price was $460, price is now $338 per person
$338
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,001 reviews)
The staff was very grumpy

Reviewed on Sep 29, 2025

Exhibit A2

Exhibit A2

4 out of 5
Downtown
Save 100% on your flight
Price was $2,585, price is now $1,516 per person
$1,516
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
8.6/10 Excellent! (353 reviews)
Such a gem in the city. This is not a typical hotel which is great. It’s a quiet apartment building that is professionally maintained. The room is super clean and just full of character. Cannot be happier with this unique accommodation. Staff really responsive to questions. There could technically be better sound insulation especially in the bathroom area but totally not an issue. Love love it.

Reviewed on Oct 8, 2025

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Price was $528, price is now $388 per person
$388
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Detroit (DTW)
9.4/10 Exceptional! (1,348 reviews)
Everything was great. The room, the venue, and the staff made for a fantastic stay.

Reviewed on Oct 12, 2025

Fort Pontchartrain Detroit, a Wyndham Hotel

Fort Pontchartrain Detroit, a Wyndham Hotel

3.5 out of 5
Downtown Detroit
Price was $1,053, price is now $800 per person
$800
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Detroit (DTW)
8.4/10 Very Good! (2,216 reviews)
Rooms was beautiful relaxing and quiet,staff was amazing, restaurants walking distance, we had all you can eat breakfast and the food was delicious, only thing is I will take public transportation the next time because they charged 45 bucks a night for parking. So when I let people know when they go use public transportation other than that I give it a 10 +

Reviewed on Oct 12, 2025

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Price was $1,154, price is now $891 per person
$891
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Detroit (DTW)
9/10 Wonderful! (1,002 reviews)
Great hotel right in the middle of Ann Arbor.

Reviewed on Oct 9, 2025

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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
University of Michigan Museum of Art showing modern architecture as well as a couple

University of Michigan Museum of Art

4.5/5(130 reviews)

Browse one of the nation’s greatest and oldest university art collections at this museum on the prestigious University of Michigan campus.

University of Michigan Museum of Art

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
$129 nightly
The price is $143 total per night from Nov 2 to Nov 3
$143 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,204 reviews)
"Excellent staff"

Reviewed on Oct 5, 2025

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

Days Inn by Wyndham Ann Arbor

2 out of 5
2380 Carpenter Road, US 23 & Washtenaw Ave, Ann Arbor, MI
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Nov 8 to Nov 9
$83 total
Nov 8 - Nov 9
Total with taxes and fees
4.6/10 (1,011 reviews)
"Met my expectations based on reviews. Great service. Easy parking. I'd stay here again."

Reviewed on Oct 6, 2025

Days Inn by Wyndham Ann Arbor
Radisson Hotel Detroit Metro Airport

Radisson Hotel Detroit Metro Airport

3 out of 5
8800 Wickham Rd, Romulus, MI
Fully refundable
$85 nightly
The price is $97 total per night from Oct 21 to Oct 22
$97 total
Oct 21 - Oct 22
Total with taxes and fees
6.8/10 (1,042 reviews)
"Property was in decent condition. Was extremely convenient location and shuttle was quick to pick up from airport. TV didn’t work but otherwise room was in decent condition and fairly clean"

Reviewed on Oct 8, 2025

Radisson Hotel Detroit Metro Airport
See all 808 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.

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 $338 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.