Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

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

The Vermont Inn

3 out of 5
Price was CA $1,457, price is now CA $1,268 per person
CA $1,268
per person
Oct 15 - Oct 19
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3-star family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Killington Resort and Golden Express Quad are located nearby.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,963, price is now CA $1,465 per person
CA $1,465
per person
Oct 15 - Oct 22
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and 8 hot tubs. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,649, price is now CA $1,384 per person
CA $1,384
per person
Oct 15 - Oct 19
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $2,026, price is now CA $1,734 per person
CA $1,734
per person
Oct 15 - Oct 22
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Four Columns Inn

Four Columns Inn

3 out of 5
Price was CA $2,272, price is now CA $2,075 per person
CA $2,075
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Yellowknife (YZF) to Rutland (RUT)
Stay at this 3-star B&B in Newfane. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Moore Free Library and Rock River Preserve are located nearby.

Top Pittsfield hotels deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $161 per night
CA $161
CA $177 total
Sep 14 - Sep 15
includes taxes & fees
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Pool
Hot tub
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $829 per night
CA $829
CA $973 total
Sep 14 - Sep 15
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
The price is CA $192 per night
CA $192
CA $211 total
Sep 17 - Sep 18
includes taxes & fees
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Pool
Breakfast included
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.
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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.

Popular places to visit

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.

Roger Clark Memorial Central Library

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.

Pittsfield Town Hall

Pittsfield Vacations

All set for your next great adventure? Ensure you don't miss out on any action in Pittsfield by learning some details about it before you hurry off.

This town lies 400 miles (644 kilometers) to the northeast of Washington, the national capital. Rutland is a nearby notable area that's just 12 miles (19 kilometers) to the south.

Places to visit in Pittsfield

Whether they're fringed by jagged mountains or a much-needed oasis in a dry and hot landscape, there's something special about lakes. Go out and see how the view looks at Lefferts Pond. Still need some more ideas? How about a bit of fun on the water? Then slap on the suntan lotion and throw yourself into some adrenaline-pumping water sports at Vermont River Tubing.

Where do you fly into for Pittsfield?

Put your seat in the upright position, stow your tray table and prepare to experience Pittsfield! Once the wheels hit the runway at Rutland Southern Vermont Regional Airport (RUT), the main streets will be only 17 miles (27 kilometers) north from here.

Frequently asked questions

How much are vacation packages to Pittsfield?
Travelocity provides flight and hotel vacation packages from as low as CA $1,268. With these kinds of deals, you'll be exploring all of Pittsfield before you know it.
How long should my Pittsfield vacation be?
Typically, 2 nights is how long the majority of people spend discovering the delights of Pittsfield. Worried you won't have sufficient time to get to everything on your must-see list? Stay a few extra nights so you don't miss a thing.
Where can I get the best vacation package deals for Pittsfield?
Travelocity is here to help you snag an awesome Pittsfield package deal. With no less than 400 air carriers and 1,000,000 properties around the world, you're sure to find the perfect combination.
Why should I book my Pittsfield vacation package with Travelocity?
Incredible savings, countless inspiring destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always get the best possible deal with Travelocity.
Will I save money on my Pittsfield car rental if I book it with hotels and flights?
With a Pittsfield vacation package, you can bundle your flight, hotel and car bookings and save a ton. If you can't wait to explore the best of this fantastic city, why not make a beeline for The Egg? This popular sight is 145 kilometers from Pittsfield. With your own set of wheels, you'll be there in no time.
Which airport is best for Pittsfield?
Burlington Intl. Airport (BTV) is 80 kilometers from the city center and is the beginning point for many memorable experiences. Alternatively, Lebanon Municipal Airport (LEB) is 40 kilometers away from central Pittsfield and Rutland Southern Vermont Regional Airport (RUT) is 29 kilometers away from central Pittsfield.
Where should I stay when visiting Pittsfield?
Many travelers opt to spend their nights at the Clear River Inn. It's sure to be a good base for your Pittsfield vacation.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration