Photo by Caitlin Reese

The Berkshires holiday rentals

We found 1,351 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024

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    Enjoy full kitchens, laundry, pools, gardens and more
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Why people love visiting captivating The Berkshires

Take a holiday to The Berkshires and enjoy the area's entertainment, museums and opera. Well known for its baseball games, hiking and skiing, this scenic city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around The Berkshires

Are you hoping to find attractions to visit during your stay? You'll be sure to enjoy The Berkshires for its hiking and skiing. Venture out of your cosy holiday rental and experience everything that makes The Berkshires a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (8.8 mi / 14.2 km)
  • Wyndhurst Golf & Club (13.6 mi / 21.9 km)
  • Catamount Ski Area (16.8 mi / 27.1 km)
  • Bousquet Ski Area (18.4 mi / 29.6 km)
  • Harney and Sons Tea Tasting Room (19.1 mi / 30.8 km)
  • Ski Sundown (22.3 mi / 35.9 km)

Exploring the natural features in The Berkshires

Whether you're an active traveller or just want to spend some time taking in the scenery, The Berkshires is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Otis Reservoir (5.7 mi / 9.1 km)
  • Lake Buel (6.5 mi / 10.4 km)
  • Goose Pond Reservation (8.2 mi / 13.3 km)
  • Housatonic River (11 mi / 17.7 km)
  • Housatonic River Walk (11 mi / 17.7 km)
  • October Mountain State Forest (12 mi / 19.2 km)

Transport options to and around The Berkshires

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 19.3 mi (31 km) from the city centre.

If you're travelling by train, make your way to Pittsfield Station or Pittsfield Intermodal Transportation Center and explore the city from there.

Frequently asked questions

What is the best area to stay in The Berkshires when booking a holiday home?

One of the most popular areas to find a The Berkshires holiday home is Hancock. When you lock in your Vrbo holiday property, you'll enjoy having the whole place to yourself. So you don't have to share it with anyone apart from your group.

What is the most popular type of holiday home accommodation in The Berkshires?

The most sought-after types of holiday homes in The Berkshires are houses. After something a little different? Vrbo has a variety of options to match our guests' needs, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get yours today.

How much does it cost to rent a holiday home in The Berkshires?

A number of things can affect what you'll pay for your holiday home in The Berkshires, such as the length of stay, type of property and season. Still, all of our holiday homes have one thing in common — incredible value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in The Berkshires?

The average price for a holiday home close to the beach in The Berkshires depends on when you're visiting the area and the size and style of property you want. Find prices easily on Vrbo by entering your preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.

What are popular home amenities in The Berkshires?

When it comes to home amenities that guests search for in The Berkshires, a microwave oven, a stovetop and a fridge are the most popular. With Vrbo holiday homes, you'll find options to fit your style and taste, whether you're travelling with family members, friends or even pets.

Are there large group holiday homes in The Berkshires?

With 94 properties that can sleep 10 guests or more in The Berkshires, there's no need to leave anyone off your guest list. From fun family get-togethers to events like birthday parties and weddings, Vrbo will help you find a large group home that fits the occasion.

What are the top attractions for families in The Berkshires?

There are lots of fun things to do and see with the family in The Berkshires, such as:

  • Bousquet Ski Area
  • Ski Butternut
  • Jiminy Peak Mountain Resort

Can I find two-bedroom holiday homes in The Berkshires?

Take your pick of 144 two-bedroom homes in The Berkshires. Give the kids the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to come along for the ride.

Are there holiday homes with WiFi in The Berkshires?

Whether you'd like to keep up with the headlines, reply to emails or post a pic to social media, there are 205 holiday homes with WiFi in The Berkshires. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How old do you have to be to rent a holiday home in The Berkshires?

You'll need to check with the Berkshires holiday home you'd like on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in The Berkshires for?

The length of time you can book a holiday home in The Berkshires depends on the property. Just enter your desired dates to display a list of options offering extended stays. With plenty of features such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in The Berkshires.