Pittsfield Vacations from $201

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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
Save 100% on your flight
Price was $346, price is now $201 per person
$201
per person
Dec 2 - Dec 6
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
5.8/10 (1,006 reviews)
The are around the property had lots of shopping and restaurants which was great.the hotel itself was very dirty,when you walk in the carpets were filthy,yoy could see the grime on the banister of the mainstairway, well had chips of paint missing and there was animal hair throughout all the main walkways. When asked to get extra towels or toilet paper my spouse was treated very rudely. The bathroom had two different types of Lights and two light bulbs out so it was very difficult to do my makeup and then there was a lamp just chilling in the closet it looks like the rooms hadn't even been put back to how they were supposed to to be. We paid extra for a Jacuzzi room and the jacuzzi didn't even work properly. Some of the staff was friendly one of them was not.

Reviewed on Sep 11, 2025

Royal Park Hotel

Royal Park Hotel

4 out of 5
Save 100% on your flight
Price was $1,517, price is now $928 per person
$928
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Detroit (DTW)
9.2/10 Wonderful! (1,001 reviews)
Beautiful hotel. Spacious well appointed rooms. Only struggle was parking. It’s a busy property with a lot of weddings. We did not use valet.

Reviewed on Oct 19, 2025

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $621, price is now $389 per person
$389
per person
Nov 25 - Nov 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,002 reviews)
Nice area beautiful everything. I loved the prayer cards the most 🙏 ♥️ Staff was top notch, will be back!!!

Reviewed on Oct 20, 2025

Holiday Inn & Suites Ann Arbor Univ Michigan Area by IHG

Holiday Inn & Suites Ann Arbor Univ Michigan Area by IHG

3 out of 5
Bryant Pattengill East
Save 100% on your flight
Price was $1,017, price is now $691 per person
$691
per person
Nov 28 - Nov 30
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (970 reviews)
Great location for transportation and restaurants.

Reviewed on Oct 21, 2025

Holiday Inn Express Auburn Hills South by IHG

Holiday Inn Express Auburn Hills South by IHG

2.5 out of 5
Price was $648, price is now $472 per person
$472
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Detroit (DTW)
8.8/10 Excellent! (548 reviews)
Amazong hotel close to everything we did

Reviewed on Sep 14, 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! (1,220 reviews)
Clean room

Reviewed on Oct 16, 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
$76 nightly
The price is $84 total per night from Oct 26 to Oct 27
$84 total
Oct 26 - Oct 27
Total with taxes and fees
4.6/10 (1,018 reviews)
Ok

Reviewed on Oct 17, 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
$94 nightly
The price is $108 total per night from Nov 4 to Nov 5
$108 total
Nov 4 - Nov 5
Total with taxes and fees
6.8/10 (1,075 reviews)
Great place near hotel

Reviewed on Oct 19, 2025

Radisson Hotel Detroit Metro Airport
See all 810 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 $201 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.