Berkshires Vacation Rentals

Vacation rental homes designed to bring you & your loved ones together for an unforgettable experience.

Make Berkshires your next getaway

Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you'll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won't find anywhere else.

Exactly what you're looking for

Berkshires vacation rentals for large groups

Berkshires pet-friendly vacation rentals

Berkshires vacation rentals with a private yard

Discover your dream vacation home in Berkshires

Sunny Pond
7 Bedrooms
4 Bathrooms
16 Guests
Wellspring
5 Bedrooms
4 Bathrooms
12 Guests
Pool
Forget-Me-Not
4 Bedrooms
4 Bathrooms
12 Guests
Chester
4 Bedrooms
3 Bathrooms
12 Guests
Half Moon
4 Bedrooms
2 Bathrooms
10 Guests
Linden
4 Bedrooms
3 Bathrooms
10 Guests
Pool
Cordelia
5 Bedrooms
3 Bathrooms
12 Guests
Woodland Zen
3 Bedrooms
2 Bathrooms
8 Guests
Whitney
5 Bedrooms
2 Bathrooms
10 Guests
Explore all stays
Frequently asked questions about Berkshires
How do you get around the Berkshires?

The best way to get around the Berkshires is by car so that you can explore the different towns and hiking spots on your own. If you don't have a car and don't want to invest in a rental, the Berkshire Regional Transit Authority offers buses to 12 cities and towns in the area at an affordable price.

With average highs of 79°F in July and lows of 15.8°F in January, all four seasons are in full swing in the Berkshires. Big temperature fluctruations mean a large range of outdoor activities for you!

  • Mountains
  • Hiking
  • Skiing
  • Snowboarding Breweries Leaf-peeping
  • Berkshire Botanical Gardens
  • Bidwell House Museum
  • Mahaiwe Performing Arts Center
  • Norman Rockwell Museum
  • Hancock Shaker Village
  • Historic Deerfield
  • Jiminy Peak Mountain Resort

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