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6 Travelers rated Pittsfield highly for Bars and Dining

Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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Top Rated Hotels for your Pittsfield Vacation

Clear River Inn
Clear River Inn
3.0 out of 5.0 2640 Route 100, Pittsfield, VT
Free Cancellation
4.0/5 (1 reviews)

Stayed here on our was to Stowe for October fest. Staff was very friendly. The tavern was great good food nice bar. This would also be great for relaxing after a day on the slopes.

Reviewed on Oct 5, 2017
Situated in Pittsfield, this inn is within 9 mi (15 km) of Green Mountain National Golf Course, Pico Mountain at Killington Ski Resort, and Gifford Woods State ...

Tips for planning your Pittsfield vacation

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Pittsfield Vacation Package Deals

Get the ball rolling on your perfect Pittsfield adventure! Let the team here at Orbitz create irrestistible flight and hotel deals.

You have the opportunity to save up to $857* when you combine your bookings. All you need to do is pick your desired hotels, airfares, rental cars and experiences.

With 500 partner airlines and more than 500,000 hotels globally, you've got the freedom to decide who you'll fly with and where you'll stay!

We know you'll find something to suit your style. Our packages offer infinite options to customize your trip along with an experience you'll always remember.

Join Orbitz Rewards

Life's a bit ordinary without those little perks and extra savings. You'll collect instant Orbucks when you keep on booking with us. This easy system rewards you lightning fast!

Interested in special perks, like complimentary breakfast and Wi-Fi, at all Orbitz Rewards VIP Hotels? Just book four nights for gold status and 12 nights for platinum in a year. And how do you redeem your Orbucks? It's a breeze! You can use your Orbitz Rewards points on your next booking.

Pittsfield Travel Guide

Where is Pittsfield?

Tickets? Check. Bags packed? Yep. Wait... where exactly are we going again? Before you jump in the airport cab, it's good to know where Pittsfield is.

It sits 12 miles to the north of Rutland, and 400 miles northeast of Washington, the nation's capital.

Places to Visit in Pittsfield

Lefferts Pond is an excellent place to enjoy some time out from the bustle of everyday life. Cast aside your shoes, feel the grass under your feet and savor the outdoors at this renowned relaxation spot. Need more options? Jump in the water and try some new skills out at Vermont River Tubing.

Car Rentals in Pittsfield

Adventure is calling, and there’s no better way to find it than with the freedom of your own ride. See and experience more by checking out car rentals in Pittsfield via Orbitz.

If you're touching down at Rutland Southern Vermont Regional Airport and would love to get your hands on a car as quickly as possible, head to Enterprise. It's at 131 S Main Street, 17 miles from the terminal.

Where to stay in Pittsfield – Hotel Accommodation

At present, Orbitz only lists 2 hotels in Pittsfield. If you're eager to stay the night, reserve your room soon.

Not sure which place to stay in? We'll simplify things! Our favorites are The Trailside Inn and The Mountain Top Inn & Resort.

Nearest Airports to Pittsfield

If you're planning on flying in to Pittsfield, you'll likely be arriving at Rutland Southern Vermont Regional Airport (RUT). Grab a coffee and get your bearings after climbing out of the plane. This is the nearest airport, sitting 17 miles away from the center of town.

Popular Places to Visit Near Pittsfield

While you're in Pittsfield, why don't you stop by some nearby localities? North Woodstock, just 60 miles away, allows easy access to Franconia Notch State Park, a well-liked attraction. Want more convincing? Loon Mountain Ski Resort is also close at hand.

No Cancellation Fees

Even the best-laid plans can change at a moment's notice, which is why we won't request a fee if you need to alter or cancel your booking.^ However, it might be a good idea to see if your selected airline and hotel have the same policy.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.