Deals on vacations and trips to Pittsfield

Save when you book Pittsfield package deals

Choose two or more items and save on your trip:

Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Harvest Barn Inn

Harvest Barn Inn

3 out of 5
Price was $658, price is now $580 per person
$580
per person
Sep 5 - Sep 7
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace is also provided.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,856, price is now $1,633 per person
$1,633
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,316, price is now $1,189 per person
$1,189
per person
Oct 1 - Oct 4
found 1 day 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.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,158, price is now $1,047 per person
$1,047
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
This hotel features free WiFi in public areas, concierge services, and free self parking. Free continental breakfast is served. A garden, a lobby fireplace, and a library are also on offer.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,401, price is now $1,270 per person
$1,270
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services, barbecue grills, and a virtual front desk are also on offer.

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.
Pool
Hot Tub
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$156 nightly
The price is $172 total per night
$172 total
Jul 30 - Jul 31
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.
Hot Tub
Pet friendly
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$240 nightly
The price is $264 total per night
$264 total
Aug 18 - Aug 19
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
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.
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.
See properties

Frequently asked questions

How much are vacation packages to Pittsfield?
Travelocity provides flight and hotel vacation packages from as low as $580. 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.