Pittsfield Trips (flight + hotel)

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Top hotels in Pittsfield

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 P7,176 per night from Aug 24 to Aug 25
P7,176
P7,966 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,151 reviews)
"It was fine"

Reviewed on Aug 4, 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
The price is P5,363 per night from Sep 1 to Sep 2
P5,363
P5,953 total
Sep 1 - Sep 2
includes taxes & fees
4.4/10 (1,007 reviews)
"This hotel is going a remodel and they are working really hard on getting everything fixed. The beds are comfortable and easy to fall asleep in"

Reviewed on Jul 29, 2025

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 P5,691 per night from Aug 17 to Aug 18
P5,691
P6,345 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (2,187 reviews)
"The staff were friendly, attentive and helpful to their guests. I will revisit this place"

Reviewed on Aug 4, 2025

La Quinta Inn & Suites by Wyndham Detroit Metro Airport
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.

What to do in Pittsfield

Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices 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?
If you're hoping to score a cheap Pittsfield vacation package, consider traveling in December, January and February. You'll usually find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Pittsfield?
With a well-planned schedule, you can easily visit the most popular Pittsfield sights in a few days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Pittsfield vacation for longer.
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.
How to plan a trip to Pittsfield?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Pittsfield.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to save for your trip to Pittsfield. Then, pick a hotel that matches your budget, whether that's a low-cost stay or a swankier getaway.
  3. Decide how long to go away for: Now that you're more familiar with Pittsfield, you can work out the right length of your vacation. Create a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Pittsfield vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.