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.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $896, price is now $769 per person
$769
per person
Nov 11 - Nov 17
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
This hotel features an indoor pool and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $1,063, price is now $833 per person
$833
per person
Nov 11 - Nov 17
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,044, price is now $825 per person
$825
per person
Nov 11 - Nov 17
found 15 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,018, price is now $874 per person
$874
per person
Nov 11 - Nov 17
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy ski-in/ski-out access and onsite ski storage. Enjoy the sauna and conveniences like express check-out and laundry facilities.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,120, price is now $973 per person
$973
per person
Nov 11 - Nov 17
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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.

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
Free Cancellation
Reserve now, pay when you stay
$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
$157 nightly
The price is $172 total per night
$172 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
$248 nightly
The price is $273 total per night
$273 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
$185 nightly
The price is $203 total per night
$203 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.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
$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.
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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 $769. 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.