Pittsfield Vacations from $345

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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.

The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
per person
Oct 17 - Oct 20
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
8.4/10 Very Good! (655 reviews)
Very friendly staff. Enjoyed my stay.

Reviewed on Jun 25, 2025

The Putney Inn

The Putney Inn

2.5 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Rutland (RUT)
8.4/10 Very Good! (1,000 reviews)
The property was clean and comfortable.

Reviewed on Aug 15, 2025

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Rutland (RUT)
8.8/10 Excellent! (858 reviews)
Love this place and we will be back again, the bed is awesome and I like all the pillows and the comfort as u feel when u walk in

Reviewed on Aug 15, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 17 - Oct 20
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Views were spectacular

Reviewed on Jul 16, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
per person
Oct 17 - Oct 20
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
9/10 Wonderful! (46 reviews)
We booked a non-smoking room. Showed up and the place ABSOLUTELY reaked of smoke. The smell was caked into everything including bedding. It was like they were smoking 10 packs plus a day and didn’t leave. Lamps and cabinets were broken as well. Cleaners also showed up at 6am blasting music, which was well before the 11am check out of the property. owners of the property did communicate well and that was much appreciated. However after this stay we are still feeling sub par out this place.

Reviewed on Aug 4, 2025

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Pittsfield Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $219 total per night from Aug 31 to Sep 1
$219 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (801 reviews)
Get away to Vermont
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."

Reviewed on Aug 14, 2025

The Shire Woodstock
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $111 total per night from Aug 19 to Aug 20
$111 total
Aug 19 - Aug 20
Total includes taxes and fees
6.2/10 (1,002 reviews)
"Staff was friendly and helpful. Nice breakfast. Comfortable bed. The bathroom needed some maintenance such as new calking around the tub. A little mildew. Ok for one night."

Reviewed on Aug 10, 2025

Days Inn by Wyndham Rutland/Killington Area
See all 1,741 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 can snap up a vacation package to this destination from $345 on Expedia. But how much your vacation to Pittsfield costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Pittsfield?
April, May and June are the best times to look for cheap Pittsfield vacation packages. Traveling in quieter periods means you can usually find better prices on accommodations and flights.
How many days is enough for Pittsfield?
The ideal length for your Pittsfield vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to visit all the leading sights and discover some hidden spots along the way.
How to find the best Pittsfield package deals?
Use Expedia's handy filters to find some great Pittsfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Pittsfield package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
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 flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom 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 have your Pittsfield travel dates finalized, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Pittsfield vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.