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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $535, price is now $434 per person
$434
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $638, price is now $502 per person
$502
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $794, price is now $659 per person
$659
per person
Oct 19 - Oct 23
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $537, price is now $459 per person
$459
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $557, price is now $488 per person
$488
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.

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
$116 nightly
The price is $128 total per night
$128 total
Sep 9 - Sep 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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$589 nightly
The price is $648 total per night
$648 total
Sep 7 - Sep 8
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
$224 nightly
The price is $246 total per night
$246 total
Sep 7 - Sep 8
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
$157 nightly
The price is $173 total per night
$173 total
Sep 14 - Sep 15
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
Sep 9 - Sep 10
Total with taxes and fees
A restaurant and an indoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free perks like on-the-go breakfast and free self parking.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $129 total per night
$129 total
Sep 7 - Sep 8
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
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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 $434. 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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