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.
Four Columns Inn

Four Columns Inn

3 out of 5
Price was $728, price is now $622 per person
$622
per person
Jan 9 - Jan 12
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 coffee shop, a garden, and a picnic area are also on offer.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,564, price is now $1,220 per person
$1,220
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $3,058, price is now $2,496 per person
$2,496
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,270, price is now $1,087 per person
$1,087
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
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.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,177, price is now $1,033 per person
$1,033
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the sauna and free perks like continental breakfast and free self parking.

Top Pittsfield hotels deals

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
$146 nightly
The price is $161 total per night
$161 total
Nov 16 - Nov 17
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
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
$116 nightly
The price is $128 total per night
$128 total
Dec 10 - Dec 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
$369 nightly
The price is $406 total per night
$406 total
Nov 30 - Dec 1
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
$175 nightly
The price is $192 total per night
$192 total
Nov 24 - Nov 25
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
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
$156 nightly
The price is $172 total per night
$172 total
Nov 16 - Nov 17
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
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $121 total per night
$121 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features an indoor pool and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast 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 $622. 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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