Pittsfield Vacations from $869

Book a Hotel + Flight or Car together to unlock savings

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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,001, price is now $869 per person
$869
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.4/10 Exceptional! (819 reviews)
Beautiful property right on the lake. We took advantage of the complimentary kayaks which was lovely. The restaurant has beautiful outdoor seating and food and service were excellent. The only negative is that we couldn’t take advantage of the fire pit or lakefront Adirondack chairs because a wedding was taking place.

Reviewed on Sep 10, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,067, price is now $922 per person
$922
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Sheets were stained staff was slow and food took way to long. 45 minutes for a grilled cheeze

Reviewed on Sep 14, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,229, price is now $1,072 per person
$1,072
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
It was really quiet. We liked our room. We stayed here for the Spartan Races weekend and they even put up some posters and chatted about the event with us. I love when local business gets implicated.

Reviewed on Sep 13, 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
Price was $1,694, price is now $1,490 per person
$1,490
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9/10 Wonderful! (47 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

The Waffelhaus In Killington 4 Bedroom Home

The Waffelhaus In Killington 4 Bedroom Home

2 out of 5
Save 100% on your flight
Price was $6,078, price is now $5,381 per person
$5,381
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
No reviews
Don't see what you're looking for?
See all available trips from Singapore to Pittsfield
View all trips

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
$134 nightly
The price is $148 total per night from Sep 18 to Sep 19
$148 total
Sep 18 - Sep 19
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"All good"

Reviewed on Sep 10, 2025

Comfort Inn Rutland - Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
$295 nightly
The price is $343 total per night from Sep 18 to Sep 19
$343 total
Sep 18 - Sep 19
Total with taxes and fees
8.6/10 Excellent! (821 reviews)
Wonderful place to stay
"We love Woodstock and this was out first time staying here at The Shire. The staff was very friendly, and the room was fun and clean, and oh what a view!"

Reviewed on Sep 14, 2025

The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$599 nightly
The price is $703 total per night from Sep 21 to Sep 22
$703 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (533 reviews)
Old world charm
"What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm."

Reviewed on Sep 12, 2025

Woodstock Inn & Resort
See all 1,735 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
You can snap up a vacation package to this destination from $869 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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