Vacation Homes in Pittsfield, MA

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Top Vacation Homes in Pittsfield

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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.

Top hotels in Pittsfield

Pittsfield Vacation Home Rentals

What kind of vacation do you want in Pittsfield? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation home is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Pittsfield that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Pittsfield, including luxury vacation home rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rental houses close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation homes a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.

Pittsfield Vacation Homes essential information

Accommodation
337 Vacation Homes
Lowest Price
$87
Highest Price
$223
Popular accommodation
Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Beautiful Berkshire Farm House on 160+ Acres, Peace and quiet on the lake, Private Estate, Heated YEARROUND Outdoor Pool, Quintessential 6-BR Berkshires Lodge, 3 Bedroom Lakefront Home with Hot Tub & Fireplace, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, A Grand property in Historic Stockbridge, Charlemont Retreat on Chickley River w/ EV Charger