Pittsfield Vacations

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    Find the right fit

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Find the Best Pittsfield Vacation Packages

Pittsfield Hotel Deals

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 ₩122,379 per night from Jul 13 to Jul 14
₩122,379
₩135,840 total
Jul 13 - Jul 14
includes taxes & fees
4.4/10 (1,005 reviews)
"Every time I travel for business to the Ann Arbor days inn. The service is great! The rooms are always clean, and it very quiet. If you need anything to make your stay more comfortable, ask Isaac and the front desk. He is always friendly and makes sure guests are well taken care of.kalways"

Reviewed on Jul 9, 2025

Days Inn by Wyndham Ann Arbor
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 ₩178,048 per night from Jul 22 to Jul 23
₩178,048
₩197,634 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,133 reviews)
"What a lovely hotel inside and out!! The furnishings, decor and set up were all beautiful. The gardens and amenities were so pretty and spacious. The included breakfast was a step above. The staff was efficient and pleasant. The one thing I wish was a bit better was the mattress, but, overall we ..."

Reviewed on Jul 7, 2025

Ann Arbor Regent Hotel & Suites
Wyndham Garden Ann Arbor
Wyndham Garden Ann Arbor
3 out of 5
2900 Jackson Ave, Ann Arbor, MI
Fully refundableReserve now, pay when you stay
The price is ₩123,740 per night from Aug 6 to Aug 7
₩123,740
₩137,351 total
Aug 6 - Aug 7
includes taxes & fees
7.2/10 Good! (1,190 reviews)
"Nice"

Reviewed on Jul 8, 2025

Wyndham Garden Ann Arbor
See all 779 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.

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.