Pittsfield Vacation Packages

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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.

Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fort Pontchartrain Detroit, a Wyndham Hotel

Fort Pontchartrain Detroit, a Wyndham Hotel

3.5 out of 5
Downtown Detroit
Price was CA $1,288, price is now CA $1,020 per person
CA $1,020
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Detroit (DTW)
8.4/10 Very Good! (2,183 reviews)
Excellent for tge Jazz everything walkable

Reviewed on Aug. 31, 2025

Royal Park Hotel

Royal Park Hotel

4 out of 5
Price was CA $1,647, price is now CA $1,189 per person
CA $1,189
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Detroit (DTW)
9.2/10 Wonderful! (1,005 reviews)
Our credit card was charged a $15 fee after check in. When questioned they said it was for the “free drink” tickets they gave us. That really put a bad taste in my mouth - not cool Royal Park! They also charged a $20 parking fee which at least they were up front about- but we parked our own car and it wasn’t even under a garage.

Reviewed on Aug. 31, 2025

Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Price was CA $1,284, price is now CA $1,030 per person
CA $1,030
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Detroit (DTW)
7.8/10 Good! (1,009 reviews)
Great courtyard! Very artsy! Friendly staff!

Reviewed on Aug. 28, 2025

Saint John's Resort

Saint John's Resort

4 out of 5
Price was CA $1,461, price is now CA $1,173 per person
CA $1,173
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Detroit (DTW)
9.6/10 Exceptional! (1,002 reviews)
Overall good experience

Reviewed on Aug. 20, 2025

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Price was CA $1,291, price is now CA $1,056 per person
CA $1,056
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Detroit (DTW)
8.6/10 Excellent! (4,007 reviews)
Rooms are very spacious loved I had a work area .

Reviewed on Sep. 1, 2025

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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
The price is CA $160 per night from Sep 2 to Sep 3
CA $160
CA $177 total
Sep 2 - Sep 3
includes taxes & fees
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
The price is CA $123 per night from Sep 28 to Sep 29
CA $123
CA $136 total
Sep 28 - Sep 29
includes taxes & fees
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
The price is CA $135 per night from Sep 7 to Sep 8
CA $135
CA $151 total
Sep 7 - Sep 8
includes taxes & fees
La Quinta Inn & Suites by Wyndham Detroit Metro Airport
See all 775 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Pittsfield

University of Michigan as well as a couple

University of Michigan

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
Exhibit Museum of Natural History at the University Of Michigan featuring interior views

Exhibit Museum of Natural History at the University Of Michigan

Science and history are fun to explore at this family-friendly museum. Exhibits are geared to appeal to students, community members and visitors.

Exhibit Museum of Natural History at the University Of Michigan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.