Deals on vacations and trips to Pittsfield

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Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $720, price is now $633 per person
$633
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $913, price is now $740 per person
$740
per person
Sep 12 - Sep 18
found 6 hours ago
Roundtrip flight included
Houston (IAH) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $785, price is now $647 per person
$647
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.
Four Columns Inn

Four Columns Inn

4 out of 5
Price was $1,483, price is now $1,269 per person
$1,269
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Rutland (RUT)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A garden and a picnic area are also provided.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $759, price is now $668 per person
$668
per person
Oct 17 - Oct 20
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Pittsfield hotels deals

Killington area home - 4-seasons, hot tub and A/C

Killington area home - 4-seasons, hot tub and A/C

Pittsfield VT
Get rates
A hot tub is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night
$527 total
Aug 16 - Aug 17
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.
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
$177 nightly
The price is $195 total per night
$195 total
Aug 2 - Aug 3
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.
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
$147 nightly
The price is $161 total per night
$161 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free Cancellation
$125 nightly
The price is $138 total per night
$138 total
Aug 9 - Aug 10
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
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
$137 nightly
The price is $149 total per night
$149 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.
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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.

Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

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

How much are vacation packages to Pittsfield?
Travelocity provides flight and hotel vacation packages from as low as $633. 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

Browse Pittsfield vacation photos for more inspiration

A lake surrounded by autumn-colored trees and a rocky shoreline.