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.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $891, price is now $796 per person
$796
per person
Nov 24 - Nov 28
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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 $931, price is now $859 per person
$859
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $955, price is now $904 per person
$904
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
This hotel features free WiFi in public areas, concierge services, and free self parking. Free continental breakfast is served. A garden, a lobby fireplace, and a library are also on offer.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $985, price is now $947 per person
$947
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $1,071, price is now $1,035 per person
$1,035
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.

Top Pittsfield hotels deals

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$156 nightly
The price is $172 total per night
$172 total
Oct 19 - Oct 20
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
$709 nightly
The price is $780 total per night
$780 total
Oct 27 - Oct 28
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
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
$154 nightly
The price is $170 total per night
$170 total
Oct 29 - Oct 30
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
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$249 nightly
The price is $274 total per night
$274 total
Oct 26 - Oct 27
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
1246 Franklin Street Brandon VT
$174 nightly
The price is $191 total per night
$191 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel's 8 hot tubs and 24-hour gym are among the featured amenities. Families will appreciate the arcade/game room and picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Pool
Hot Tub
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
$129 nightly
The price is $141 total per night
$141 total
Oct 27 - Oct 28
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
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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 $796. 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.