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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $671, price is now $522 per person
$522
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $1,418, price is now $1,184 per person
$1,184
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rutland (RUT)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
The Landgrove

The Landgrove

3.5 out of 5
Price was $1,240, price is now $1,080 per person
$1,080
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
This inn features a restaurant, a seasonal outdoor pool, and a bar/lounge. Families will appreciate the playground and onsite laundry facilities. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $985, price is now $928 per person
$928
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A lobby fireplace, a communal living room, and luggage storage are also on offer.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $928, price is now $882 per person
$882
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
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.

Top Pittsfield hotels deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free Cancellation
$125 nightly
The price is $138 total per night
$138 total
Nov 15 - Nov 16
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
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
Dec 8 - Dec 9
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
$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
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
$165 nightly
The price is $181 total per night
$181 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a hot tub and a sauna. Families will appreciate the arcade/game room and picnic area. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.
Hot Tub
Breakfast included
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$181 nightly
The price is $200 total per night
$200 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
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
$150 nightly
The price is $165 total per night
$165 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features a 24-hour gym, a hot tub, and a restaurant. 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
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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.

Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Frequently asked questions

How much are vacation packages to Pittsfield?
Travelocity provides flight and hotel vacation packages from as low as $522. 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

Browse Pittsfield vacation photos for more inspiration

A lake surrounded by autumn-colored trees and a rocky shoreline.