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Top Pittsfield hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $541 per night
CA $541
CA $657 total
Jan 20 - Jan 21
includes taxes & fees
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 Middle Covered Bridge and Woodstock Town Hall Theatre 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 $238 per night
CA $238
CA $262 total
Jan 28 - Jan 29
includes taxes & fees
Book a stay at this 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
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 $195 per night
CA $195
CA $215 total
Feb 1 - Feb 2
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
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
Free cancellation
Reserve now, pay when you stay
The price is CA $249 per night
CA $249
CA $274 total
Jan 25 - Jan 26
includes taxes & fees
Book a stay at this ski hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pico Mountain at Killington Ski Resort and Green Mountain Rock Climbing Center are located nearby.
Pool
Breakfast included
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
CA $149 total
Feb 8 - Feb 9
includes taxes & fees
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Pet-friendly
Parking 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
The price is CA $223 per night
CA $223
CA $245 total
Jan 21 - Jan 22
includes taxes & fees
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.

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 . 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