Vacation Homes in Pittsfield

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Featured 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.

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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
436 Vacation Homes
Lowest Price
$101
Highest Price
$278
Popular accommodation
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub., ☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, Spacious 3-story home near ski area with private hot tub, Ping-Pong, Cozy private country setting - 15 miles from Woodstock, Upscale VT Getaway by Slopes, Lakes & Trails!, Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10304, 4 Season Secluded Lakefront Home near Ski Mountains , Post & Beam Home Ideal for families or Groups, Bright, Family-Friendly Lake View House Close to Okemo, Killington, Pico, Lakes