Pittsfield Vacations from $404

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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 Putney Inn

The Putney Inn

2.5 out of 5
Price was $508, price is now $404 per person
$404
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
8.4/10 Very Good! (1,005 reviews)
My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term accommodation.

Reviewed on Aug 22, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,622, price is now $1,274 per person
$1,274
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug 22, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $555, price is now $444 per person
$444
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
6.4/10 (1,005 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug 18, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,124, price is now $939 per person
$939
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $639, price is now $537 per person
$537
per person
Sep 29 - Oct 3
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.4/10 Exceptional! (814 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug 12, 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 with taxes and fees
9.2/10 Wonderful! (532 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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $144 total per night from Aug 27 to Aug 28
$144 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug 23, 2025

The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $233 total per night from Aug 26 to Aug 27
$233 total
Aug 26 - Aug 27
Total with taxes and fees
8.6/10 Excellent! (807 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on Aug 21, 2025

The Shire Woodstock
See all 1,734 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 $404 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.