Pittsfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.
Saint John's Resort

Saint John's Resort

4 out of 5
Price was CA $1,433, price is now CA $965 per person
CA $965
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Detroit (DTW)
9.6/10 Exceptional! (1,007 reviews)

The Townsend Hotel

The Townsend Hotel

4 out of 5
Price was CA $2,075, price is now CA $1,439 per person
CA $1,439
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Detroit (DTW)
9.2/10 Wonderful! (786 reviews)

Stadium Suites

Stadium Suites

3 out of 5
Save 100% on your flight
Price was CA $1,911, price is now CA $1,328 per person
CA $1,328
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Detroit (DTW)
8.6/10 Excellent! (30 reviews)

Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Price was CA $1,400, price is now CA $1,023 per person
CA $1,023
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Detroit (DTW)
8.4/10 Very good! (1,326 reviews)
Easy. CHeck in and out. Hotel and room clean location convenient for where we were going. Wish complementary coffee was provided. Room didn’t have face towels. Pretty sure would have been easy to get but I brought my own for my one night stay.

Reviewed on Sep 22, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Price was CA $1,611, price is now CA $1,254 per person
CA $1,254
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Detroit (DTW)
9.4/10 Exceptional! (1,578 reviews)
The front desk staff who checked us in were lovely and made our stay great from the start by accommodating an early check-in. I really enjoyed the restaurant's rich history, excellent food, and attentive service, and the bar was cozy and inviting. The aromatherapy in the hallways was a fantastic touch as well. The room exceeded expectations—the bathroom's Bluetooth mirror made listening to music in the rain shower so much fun, and the heated seat bidet was a wonderful luxury. Also, taking the $3.00 round-trip shuttle bus to the University of Michigan game was incredibly convenient. We will definitely be staying here again! Best, Shawn Dee Hartless

Reviewed on Sep 21, 2026

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 $173 per night from Oct 18 to Oct 19
CA $173
CA $192 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (1,630 reviews)
"Room was clean and beds were comfortable. Pillows were better than most other places I’ve been. Didn’t try the breakfast but did have coffee. The hotel over all was quiet and a good location."

Reviewed on Sep 22, 2026

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

Days Inn by Wyndham Ann Arbor

2 out of 5
2380 Carpenter Road Ann Arbor MI
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Sep 23 to Sep 24
CA $105
CA $117 total
Sep 23 - Sep 24
includes taxes & fees
5/10 (1,045 reviews)
"This was a last minute booking and I regret my stay here. The room was very dirty, unkept, missing items and damaged. The door did not have a functioning chain lock, the remote was missing and the shower handle fell off as some as I touched it. The jetted tub had dead bugs and hair in it making it ..."

Reviewed on Sep 21, 2026

Days Inn by Wyndham Ann Arbor
Quality Inn & Suites Ann Arbor Hwy 23

Quality Inn & Suites Ann Arbor Hwy 23

2.5 out of 5
2376 Carpenter Rd. Ann Arbor MI
Fully refundable
The price is CA $112 per night from Sep 29 to Sep 30
CA $112
CA $124 total
Sep 29 - Sep 30
includes taxes & fees
4.8/10 (1,001 reviews)
"2nd class dump!"

Reviewed on Sep 22, 2026

Quality Inn & Suites Ann Arbor Hwy 23
See all 831 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

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.
See properties

What to do in Pittsfield

Shaanxi Archaeological Museum English-speaking Guide Service

Shaanxi Archaeological Museum English-speaking Guide Service

CA $69
per adult
100% of travellers recommend
Shaanxi Archaeological Museum English-speaking Guide Service
Italian Pasta Cooking Class in Detroit

Italian Pasta Cooking Class in Detroit (Includes 3-Course Meal)

CA $179
per adult
Italian Pasta Cooking Class in Detroit (Includes 3-Course Meal)
See all activities in Pittsfield

Frequently asked questions

How much does a Pittsfield vacation package cost?
You can pick up a vacation package to this top destination from CA $965 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.