Pittsfield Vacations from $705

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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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
8.6/10 Excellent! (1,001 reviews)
Good value hotel in an excellent location.

Reviewed on Jun 29, 2025

Super 8 by Wyndham Ticonderoga

Super 8 by Wyndham Ticonderoga

2.5 out of 5
per person
Aug 2 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
8/10 Very Good! (1,005 reviews)
Friendly helpful staff, clean, and great for the price. Next door to McDonald's amd Walmart, short walk to good convenience store. Us Adirondack taxi! $5 to downtown $15 to train station from hotel

Reviewed on Jun 30, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
7.2/10 Good! (1,003 reviews)
Located not very far from the main road, very peaceful. So grateful that they are a pet friendly resort.

Reviewed on Jul 1, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
9.2/10 Wonderful! (402 reviews)
Excellent. Jeanine was so kind and helpful. Really cute sitting room. Sauna was awesome. Quiet and clean!

Reviewed on May 25, 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
9.4/10 Exceptional! (31 reviews)
We stayed here for the weekend for a wedding and it was so comfortable, clean, and quiet since you get your own cabin. We loved it and would definitely come back! The property was also really accommodating to requests and needs in a timely manner

Reviewed on May 16, 2025

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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
$131 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total includes taxes and fees
8/10 Very Good! (1,001 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."

Reviewed on Jun 26, 2025

Comfort Inn Rutland - Killington
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
$469 nightly
The price is $516 total per night from Jul 6 to Jul 7
$516 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (521 reviews)
"Relaxing"

Reviewed on Jun 25, 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
$139 nightly
The price is $152 total per night from Jul 13 to Jul 14
$152 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,000 reviews)
"Pleasant stay"

Reviewed on Jun 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,748 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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
540
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Center

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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 $705 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.