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Pittsfield flight + hotel packages

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Brandon Inn

Brandon Inn

3 out of 5
per person
Feb. 17 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3-star hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stephen A Douglas Birthplace and Judith Reilly Gallery are located nearby.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
per person
Feb. 17 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3-star golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Wilderness Trails and Vermont Institiute of Natural Science are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
per person
Feb. 17 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3.5-star beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
Jan. 20 - Jan. 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
per person
Feb. 17 - Feb. 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.

Top Pittsfield hotels deals

Killington area home - 4-seasons & hot tub. Sleeps 12+

Killington area home - 4-seasons & hot tub. Sleeps 12+

Get rates
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and tennis courts. Popular attractions White River Golf Club and Appalachian Trail Adventures are located nearby.
Hot tub
Kitchen
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 $156 per night
CA $156
CA $171 total
includes taxes & fees
15 Dec - 16 Dec
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 Paramount Theater are located nearby.
Pool
Hot tub
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $243 per night
CA $243
CA $268 total
includes taxes & fees
18 Dec - 19 Dec
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 Pico Mountain at Killington Ski Resort are located nearby.
Hot tub
Pet-friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $433 per night
CA $433
CA $538 total
includes taxes & fees
16 Dec - 17 Dec
Book a stay at this 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 Woodstock Town Hall Theatre and Red Wagon Toy Company are located nearby.
Pool
Hot tub
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
Free cancellation
Reserve now, pay when you stay
The price is CA $135 per night
CA $135
CA $148 total
includes taxes & fees
3 Dec - 4 Dec
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Diamond Run Mall and Vermont State Fairgrounds are located nearby.
Breakfast included
Pet-friendly
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
The price is CA $149 per night
CA $149
CA $164 total
includes taxes & fees
3 Dec - 4 Dec
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 Pico Mountain at Killington Ski Resort are located nearby.
Pool
Parking included
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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.

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 $822. 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