Pittsfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Saint John's Resort
CA $1,422
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Detroit (DTW)
9.6/10 Exceptional! (1,010 reviews)
This place has a great atmosphere for relax. Elegant, cleand and quiet. Thre restaurants to chose good food. Higlhly recomended for a geat away weekend. We used it because we had an event near by. So it was only one night. Next time we stay longer for sure.
Reviewed on Aug 26, 2026
The Siren Hotel, an Ash Hotel
Downtown Detroit
CA $1,632
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Detroit (DTW)
9/10 Wonderful! (2,149 reviews)
Super friendly staff in all departments. Beautifully decorated historic hotel. Very central to everything.
The staff clearly communicated the hotels free drink policy. However, it is strange to provide one free drink in a room with two guests.
Reviewed on Aug 26, 2026
MotorCity Casino Hotel
North Corktown
CA $1,591
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Detroit (DTW)
8.8/10 Excellent! (4,757 reviews)
Absolutely loved my stay. The revamped rooms are great and staff very helpful. Casino is bright and clean. I only wish the spa was open when I visited. Oh and the bathtub rocks!
Reviewed on Aug 26, 2026
Ann Arbor Marriott Ypsilanti at Eagle Crest
CA $1,356
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Detroit (DTW)
8.6/10 Excellent! (673 reviews)
They charged $30 for parking. When I was last there, parking was free. I don’t know how they justify a $30 charge on a rural property. Ypsilanti is not downtown Detroit. I will never stay there again.
Reviewed on Aug 26, 2026
Ready to book your vacation to Pittsfield?
Pittsfield Hotel Deals
Ann Arbor Regent Hotel & Suites
2455 Carpenter Road Ann Arbor MI
Fully refundableReserve now, pay when you stay
CA $153
CA $170 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,585 reviews)
"The room was really nice and clean. It definitely exceeded our expectations."
Reviewed on Aug 27, 2026
Days Inn by Wyndham Ann Arbor
2380 Carpenter Road Ann Arbor MI
Fully refundableReserve now, pay when you stay
CA $108
CA $120 total
Aug 30 - Aug 31
includes taxes & fees
5/10 (1,003 reviews)
"We left. The room reeked of cigarette smoke. Pool was not on the property. We couldn’t get out fast enough!"
Reviewed on Aug 26, 2026
Wyndham Garden Ann Arbor
2900 Jackson Ave Ann Arbor MI
Fully refundableReserve now, pay when you stay
CA $97
CA $108 total
Sep 16 - Sep 17
includes taxes & fees
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.
Stay near popular Pittsfield attractions
Briarwood Mall
8.4/10 (1,001 reviews)
You can enjoy retail therapy at Briarwood Mall during your trip to Ann Arbor. You can attend a sporting event while in the area.
Stonebridge Golf Club
7.4/10 (17 reviews)
Enjoy a round of golf in Pittsfield at Stonebridge Golf Club. You can attend a sporting event while in the area.
University of Michigan Golf Course
Enjoy a round of golf in Ann Arbor at University of Michigan Golf Course.
Lake Forest Golf Club
Enjoy a round of golf in Ann Arbor at Lake Forest Golf Club. You can attend a sporting event while in the area.
Cinemark Ann Arbor 20 and IMAX
You can take time to visit Cinemark Ann Arbor 20 and IMAX during your travels to Pittsfield.
Varsity Tennis Center
Catch an event at Varsity Tennis Center during your trip to Ann Arbor.
Miles of Golf
You can take time to visit Miles of Golf during your travels to Pittsfield.
Ann Arbor Golf & Outing Club
Enjoy a round of golf in Ann Arbor at Ann Arbor Golf & Outing Club.
What to do in Pittsfield
Italian Pasta Cooking Class in Detroit (Includes 3-Course Meal)
CA $181
per adult
Frequently asked questions
How much does a Pittsfield vacation package cost?
You can pick up a vacation package to this top destination from CA $1,238 on Expedia. But how much your vacation to Pittsfield costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Pittsfield?
You can generally find lower rates and better availability in December, January and February. Take a look at our cheap Pittsfield vacation packages and you could score some great off-season deals.
How many days is enough for Pittsfield?
With a well-planned itinerary, you can easily hit the top Pittsfield attractions in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Pittsfield vacation for longer.
How to find the best Pittsfield package deals?
Use Expedia's handy filters to find some tempting Pittsfield package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Pittsfield package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pittsfield?
Enjoy incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Pittsfield getaway.
How to plan a trip to Pittsfield?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Pittsfield.
- Set your budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Pittsfield. Then, choose a hotel that works with your budget, whether that's a wallet-friendly option or a more luxurious getaway.
- Determine how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Pittsfield. Then, estimate how long you'll need for each, along with any travel time.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Pittsfield vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
