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.
Summit Lodge

Summit Lodge

3 out of 5
Price was $935, price is now $807 per person
$807
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
This smoke-free inn features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,452, price is now $1,075 per person
$1,075
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,187, price is now $941 per person
$941
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
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.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,416, price is now $1,135 per person
$1,135
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 and a virtual front desk are also provided.
Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,530, price is now $1,312 per person
$1,312
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
A full-service spa and a gym are featured at this apartment. Free self parking and laundry facilities are also offered on site.

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
$144 nightly
The price is $158 total per night
$158 total
Jan 4 - Jan 5, 2026
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
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
$204 nightly
The price is $225 total per night
$225 total
Jan 21 - Jan 22, 2026
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
$272 nightly
The price is $299 total per night
$299 total
Dec 23 - Dec 24
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night
$395 total
Jan 19 - Jan 20, 2026
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
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
$160 nightly
The price is $176 total per night
$176 total
Jan 4 - Jan 5, 2026
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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $179 total per night
$179 total
Jan 11 - Jan 12, 2026
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
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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 $807. 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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