Pittsfield Vacation Packages

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Your Pittsfield Vacation

Get ready to experience Pittsfield in your own style with a custom Pittsfield vacation package! Uncovering the charms of this captivating city is made easier with a base in a neighborhood such as West Bridgewater, which is good for skiing, among many other things. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just some of the many sights you'll want to see during your trip to Pittsfield. A couple of quick clicks is all it takes to put together your perfect Pittsfield vacation on Expedia.

Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Putney Inn

The Putney Inn

2.5 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rutland (RUT)
8.4/10 Very Good! (1,000 reviews)
Nice, quiet spot for a night heading up to camp. Older building but kept clean and comfortable.

Reviewed on Jul. 21, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rutland (RUT)
9.2/10 Wonderful! (403 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul. 23, 2025

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rutland (RUT)
8.4/10 Very Good! (647 reviews)
Very friendly staff. Enjoyed my stay.

Reviewed on Jun. 25, 2025

Harvest Barn Inn

Harvest Barn Inn

3 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rutland (RUT)
9.8/10 Exceptional! (219 reviews)
This was our second stay! Perfect. Breakfast was super delicious and beautifully presented by Kaelan. We were greeted upon arrival and had an excellent stay. Kaelan and Blessing are fantastic hosts. Thank you!! We will be back again soon.

Reviewed on Jul. 7, 2025

Greenbrier Inn

Greenbrier Inn

2 out of 5
per person
Oct 1 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Rutland (RUT)
9.6/10 Exceptional! (606 reviews)
A cozy, nicely decorated, and unique accomodation that was adjacent to both Killington and Pico ski resorts. The rooms and amenities were slightly outdated but they were clean and functional. The staff was very friendly and helpful. The large gift shop had a tasteful selection of items.

Reviewed on Jul. 21, 2025

Ready to book your vacation to Pittsfield?

 

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Pittsfield Hotel Deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Aug 18 to Aug 19
CA $171
CA $188 total
Aug 18 - Aug 19
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"Hotel was good. Was a great steakhouse next door. Hotel breakfast what you would expect. No problems"

Reviewed on Jul. 21, 2025

Comfort Inn Rutland - Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $613 per night from Aug 17 to Aug 18
CA $613
CA $734 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (528 reviews)
"Really enjoyed our stay."

Reviewed on Jul. 18, 2025

Woodstock Inn & Resort
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Aug 3 to Aug 4
CA $208
CA $229 total
Aug 3 - Aug 4
includes taxes & fees
7.2/10 Good! (1,005 reviews)
Family reunion.
"Our room was not ready when we arrived at 4:20. The person checking us in was very apologetic and offered us a glass of wine, and breakfast. We really appreciated that!"

Reviewed on Jul. 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,739 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.
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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from CA $1,357 on Expedia for your Pittsfield getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
To score cheap Pittsfield vacation packages, organize your trip outside of peak periods like public holidays and major events. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Pittsfield?
With a well-planned schedule, you can easily tick off the main Pittsfield sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Pittsfield vacation for longer.
How to find the best Pittsfield package deals?
Start your search for a Pittsfield package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Pittsfield package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pittsfield adventure underway.
Is it cheaper to book a Pittsfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Pittsfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates confirmed, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Pittsfield?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite season and the type of activities on offer will also help you decide when to visit Pittsfield.
  2. Plan your budget wisely: Besides the cost of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could arise during your trip to Pittsfield.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Pittsfield. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've settled on your dates and duration, book the perfect Pittsfield vacation package for you.

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