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.
Killington Haus

Killington Haus

2 out of 5
Price was $544, price is now $524 per person
$524
per person
Dec 5 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a virtual front desk are also provided.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $718, price is now $613 per person
$613
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $759, price is now $677 per person
$677
per person
Dec 30 - Jan 3
found 18 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $598, price is now $549 per person
$549
per person
Dec 5 - Dec 8
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $877, price is now $832 per person
$832
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Top Pittsfield hotels deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free Cancellation
$124 nightly
The price is $136 total per night
$136 total
Nov 16 - Nov 17
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.
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
Oct 28 - Oct 29
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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$409 nightly
The price is $450 total per night
$450 total
Nov 16 - Nov 17
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.
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 10 - Nov 11
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.
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 16 - Nov 17
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.
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
Nov 22 - Nov 23
Total with taxes and fees
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A communal living room and luggage storage are also provided.
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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 $524. 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.