Discover a selection of 1,000 vacation rentals in The Berkshires, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $164 per night, and houses and cabins are popular options for a stay in The Berkshires. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — The Berkshires
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What are the top vacation rentals in The Berkshires?

Elegant condos, unique treehouses and quaint cottages — everyone's ideal escape is different. Whatever you're into, you're sure to find something that catches your eye among our top vacation rentals in The Berkshires:

  • "Close To Skiing Beautiful +family Friendly": If you're looking for a comfy living space in Sheffield, this rental won't disappoint. It comes with 4 bedrooms and a host of amenities including pet-friendly services and games.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi": Put your bags down and your feet up at this top pick in Otis. It comes with 4 bedrooms, lowered locks, cable/satellite TV services and more.

For even more great options, use the search bar at the top of the page to find the perfect The Berkshires vacation rental for you.

Can I find log cabins to rent in The Berkshires?

There's something inherently cozy about relaxing in a log cabin with a cup of coffee and a good book. Leave the busyness of everyday life behind and spend a few nights or more at one of these log cabins in The Berkshires:

  • If you want to go water skiing or snowboarding while you're in The Berkshires, "Water Front Log Cabin Next To Tanglewood" in West Stockbridge will be a terrific choice.
  • Alternatively, consider "Cozy Log Cabin Adjacent To Beartown Forest". Try some skiing or mountain biking or simply put your feet up at this Great Barrington getaway.

What are the top-rated vacation rentals for weekend getaways in The Berkshires?

After a hectic week, a quick break packed with adventure will be exactly what you need to refresh your spirit. Take a peek at these leading weekend getaways in The Berkshires where you can pack some serious fun into your stay:

  • "Elterwater - - Your Lakefront Oasis" in Sheffield is an excellent choice if you want to spend time outdoors. Get out and see the area's best natural attractions, such as Tyringham Cobble and Skyline Trail, or try some fun activities. Horse riding and hiking and biking are two ways to get your kicks.
  • You'll be able to fit a whole lot into your weekend away at "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences". This property is located in Peru and is within reach of top sights like Petticoat Hill and Skyline Trail. Fishing and hiking and biking are some cool experiences that are also on your doorstep.

Can I find studio apartments for rent in The Berkshires?

You'll find plenty of studio apartments in The Berkshires. While they obviously can't compete in size with a mansion, they sure do pack a punch when it comes to convenience, character and location. Here are two sought-after options:

  • "Cabin - A - Frame In Sherwood Forest" is a cozy getaway Becket. You'll have lots of amenities to make the most of here, including beach towels and shopping. When it's time to explore some nearby cultural sights, Springfield Museums and Barrington Stage Company should be among them.
  • "Renovated Downtown 1bedroom" in Lenox is another great option that offers towels and a washing machine. Double Edge Theatre and Berkshire Theatre Festival should be on your to-do list in this area.

Can I find short term rentals in The Berkshires?

There's nothing like heading off on a quick getaway to explore a place that you've never been to before. Check out these short-term rentals in The Berkshires and cross one more destination off your must-see list:

  • "Elterwater - - Your Lakefront Oasis" in Sheffield is an excellent place to base yourself. Stay here and you'll be within reach of top sights including Ski Butternut.
  • Alternatively, make your home away from home at "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences". This Costa Calida property will put you near Glendale Falls and loads of other interesting attractions.

What are the best romantic weekend getaways in The Berkshires?

If you're eager to dazzle your someone special, then stay somewhere special! Organize a romantic weekend getaway in The Berkshires at one of these properties and let love blossom:

  • Catch up on cuddles and quality time at "Close To Skiing Beautiful +family Friendly" in Sheffield. Skiing facilities and a fireplace are among the thoughtful touches on offer here.
  • Alternatively, plan a weekend of canoodling at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". A balcony and shopping facilities add to the idyllic atmosphere of this property in Otis.

What are the best large group vacation rentals in The Berkshires?

When it comes to who you go on vacation with, we think the more people the merrier. If you're after a property with plenty of space to fit the ones you love, one of these large group vacation rentals in The Berkshires will satisfy your needs:

  • "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History": This popular rental is a great choice for large groups planning to stay in Lenox. It has 6 bedrooms and amenities that include a kitchen and a firepit.
  • "General Williams Estate House Lenox": This property in Stockbridge has 6 bedrooms, so you won't have to leave anybody off your invite list. A kitchen and a fireplace are some of its many highlights.

What are the best houses for rent with a pool in The Berkshires?

Get set to take your pick and dive right in. Here are a couple of top-rated house rentals in The Berkshires where memories are made at the pool:

  • Say hello to "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", where the first item on your itinerary should be taking a dip in the pool. This retreat is located in Otis and offers a host of family-friendly amenities, including childrens activities and a separate dining area.
  • Leap out of bed and go for an early morning dip at "Charming Berkshire Getaway In A Modern Comfortable House" in Gulfport. A barbecue grill and a theme park are just two of the many amenities offered here.

What are the best large family vacation rentals in The Berkshires?

Start putting together your guest list, because Vrbo has tons of family vacation rentals in The Berkshires that'll lay out the welcome mat for your gang. Here are a few of our top picks:

  • If you'd like a rental that sleeps no fewer than 9 people, lock in "88 Acres Of Beauty In The Berkshires" in Sheffield. With 4 bedrooms, a pool table and a balcony, your next family vacation will be one you won't forget.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi" in Otis is another favorite with families. You'll be able to invite up to 10 guests to this escape which has 4 bedrooms, a porch, a stereo and more.

Can I find family cabin rentals in The Berkshires?

Renting a cabin in The Berkshires is the perfect way to spend quality time with the family. Consider these options:

  • "Cabin - A - Frame In Sherwood Forest" - Book a weekend or more at this retreat in Becket. Amenities like childrens activities and a video library will help make your stay nice and comfy.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - Amenities like on-site watersports and a separate dining area also make this a popular choice among families. Escape to this Sherwood Forest property and enjoy some time in Mother Nature.

For more options, use the search bar at the top of the page and adjust the filters to find the Berkshires vacation rental that's perfect for your needs.