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.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $1,212, price is now $1,114 per person
$1,114
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Rutland (RUT)
This smoke-free guesthouse features a full-service spa and a restaurant. A convenience store and wedding services are also provided.
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Price was $2,574, price is now $2,476 per person
$2,476
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Rutland (RUT)
This castle doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace is also provided.

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.
Hot Tub
Kitchen
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
$155 nightly
The price is $170 total per night
$170 total
May 10 - May 11
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
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
May 25 - May 26
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
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $172 total per night
$172 total
May 3 - May 4
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
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
$109 nightly
The price is $119 total per night
$119 total
May 31 - Jun 1
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.
Pet friendly
Parking included
Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
$109 nightly
The price is $120 total per night
$120 total
May 21 - May 22
Total with taxes and fees
A restaurant, free self parking, and a communal living room are among this hotel's amenities. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage and concierge services are also provided.
Breakfast included
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 $1,114. 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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