Deals on vacations and trips to Pittsfield

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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
$119 nightly
The price is $131 total per night
$131 total
Sep 10 - Sep 11
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$639 nightly
The price is $703 total per night
$703 total
Sep 14 - Sep 15
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
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
$245 nightly
The price is $270 total per night
$270 total
Sep 10 - Sep 11
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
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
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $158 total per night
$158 total
Sep 15 - Sep 16
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Hot Tub
Pet friendly
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
$148 nightly
The price is $162 total per night
$162 total
Sep 18 - Sep 19
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.
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
$117 nightly
The price is $129 total per night
$129 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
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

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 90 mi 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 50 mi from the city center and is the beginning point for many memorable experiences. Alternatively, Lebanon Municipal Airport (LEB) is 25 mi away from central Pittsfield and Rutland Southern Vermont Regional Airport (RUT) is 18 mi 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

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