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.
Harvest Barn Inn

Harvest Barn Inn

3 out of 5
Price was $856, price is now $731 per person
$731
per person
Apr 29 - May 3
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) 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
Save 100% on your flight
Price was $1,702, price is now $1,304 per person
$1,304
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,327, price is now $1,096 per person
$1,096
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $2,882, price is now $2,405 per person
$2,405
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities and barbecue grills are also provided.
Mt Green 3-f04 in Killington

Mt Green 3-f04 in Killington

2 out of 5
Price was $1,383, price is now $1,175 per person
$1,175
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
A full-service spa and a gym are featured at this apartment. Enjoy the sauna and perks like free self parking and free WiFi. Laundry facilities and barbecue grills are also provided.

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
$152 nightly
The price is $167 total per night
$167 total
Feb 9 - Feb 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.
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
$156 nightly
The price is $172 total per night
$172 total
Mar 1 - Mar 2
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.
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
$148 nightly
The price is $162 total per night
$162 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features a 24-hour gym and an outdoor tennis court. Enjoy the free ski shuttle and onsite ski storage. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night
$384 total
Feb 22 - Feb 23
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.
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
$96 nightly
The price is $105 total per night
$105 total
Mar 2 - Mar 3
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.
Summit Lodge

Summit Lodge

3 out of 5
200 Summit Road Killington VT
$193 nightly
The price is $212 total per night
$212 total
Feb 9 - Feb 10
Total with taxes and fees
This smoke-free inn features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
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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 $731. 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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