Vacation Homes in The Berkshires

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Featured Vacation Homes in The Berkshires

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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 trending hotels in The Berkshires

Vacation Rentals in The Berkshires

What kind of vacation do you want in The Berkshires? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental 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 The Berkshires 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 The Berkshires, including luxury vacation 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 rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals 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.

The Berkshires Vacation Homes essential information

Accommodation
254 Vacation Homes
Lowest Price
CA $131
Highest Price
CA $366
Popular accommodation
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Amore Estate - beautiful room with many places to explore and relax in., Secluded Family Home in Serene Stockbridge Woods, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Tranquil 3-BR Waterfront Retreat, Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow, NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE