Pittsfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

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.
American Inn and Suites Dundee

American Inn and Suites Dundee

2 out of 5
Price was CA $650, price is now CA $474 per person
CA $474
per person
Oct 15 - Oct 19
found 9 hours ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
7/10 Good! (938 reviews)
Everyone was super friendly and made our stay so much fun!

Reviewed on Sep 3, 2025

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Price was CA $4,339, price is now CA $2,398 per person
CA $2,398
per person
Oct 15 - Oct 19
found 9 hours ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
9/10 Wonderful! (1,009 reviews)
We loved our stay! It was a perfect location as we were visiting our son who goes to college there. The apartment was clean and had everything we needed. The yummy blank slate creamery ice cream shop was right across the street which was a bonus! We will definitely be staying again the next time we visit Ann Arbor.

Reviewed on Aug 25, 2025

Holiday Inn Express & Suites Ann Arbor West by IHG

Holiday Inn Express & Suites Ann Arbor West by IHG

2.5 out of 5
Price was CA $1,250, price is now CA $871 per person
CA $871
per person
Oct 15 - Oct 19
found 9 hours ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
9/10 Wonderful! (815 reviews)
The breakfast was very plain and only mashed eggs, thin pancakes when working and sausages that seemed a bit undercooked. The staff however were very pleasant and helpful.

Reviewed on Sep 9, 2025

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Price was CA $1,638, price is now CA $1,146 per person
CA $1,146
per person
Oct 15 - Oct 19
found 9 hours ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
9.4/10 Exceptional! (1,339 reviews)
Everything was perfect but food: absolutely unreal

Reviewed on Sep 8, 2025

The Kensington Hotel

The Kensington Hotel

3.5 out of 5
Bryant Pattengill West
Price was CA $1,821, price is now CA $1,336 per person
CA $1,336
per person
Oct 15 - Oct 19
found 9 hours ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
8.6/10 Excellent! (1,025 reviews)
Love the lit courtyard

Reviewed on Sep 2, 2025

Ready to book your vacation to Pittsfield?

 

Choose your dates

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 10 to Sep 11
CA $160
CA $178 total
Sep 10 - Sep 11
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 10 to Sep 11
CA $123
CA $137 total
Sep 10 - Sep 11
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 $136 per night from Sep 21 to Sep 22
CA $136
CA $151 total
Sep 21 - Sep 22
includes taxes & fees
La Quinta Inn & Suites by Wyndham Detroit Metro Airport
See all 776 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.