1645+ Vacation Home Rentals in The Berkshires |
  1. USA
  2. Massachusetts
  3. The Berkshires

The Berkshires Vacation Rentals & Ski-in/Ski-out Homes

About The Berkshires Vacation Rentals

Explore over 1645 vacation rentals in The Berkshires with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in The Berkshires for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in The Berkshires. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in The Berkshires tailored to your preferences. On average, these rentals offer 1046.33 ft² of space, and are priced at an average of US $443 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in The Berkshires at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Show more
Show less

Top Types of Ski Accommodations in The Berkshires

Type Count
Vacation Homes 867
Holiday Apartments 179
Cottages 77
Cabin Rentals 58
B&B 54
Others 26
Ski Chalet Rentals 12
Villas 12
Unique Vacation Rentals 2

Use these Quick Filters to Find a Vacation Rental in The Berkshires

★ Pro Tip: Discover Your Ideal Vacation Rental in The Berkshires with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in The Berkshires, MA

View the weather forecast for The Berkshires before booking your The Berkshires Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around The Berkshires, MA

Sunski offers a large selection of top attractions around The Berkshires . Research things to do on your vacation before you visit The Berkshires.


Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
Norman Rockwell Museum
National Shrine of the Divine Mercy
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Hancock Shaker Village
Otis Ridge
Pittsfield State Forest
October Mountain State Forest
Beartown State Forest
Savoy Mountain State Forest

Other Places to Stay in The Berkshires, MA


Berkshire County 1,017 Properties
Great Barrington 157 Properties
Hancock 147 Properties
Jiminy Peak Mountain Resort 147 Properties
Lenox 98 Properties
Williamstown 83 Properties
Pittsfield 72 Properties
Lee 57 Properties
Becket 47 Properties
Stockbridge 43 Properties
New Marlborough 36 Properties
North Adams 36 Properties

Complexes around The Berkshires, MA


Wyndham Bentley Brook 34 Properties
Jiminy Peak 28 Properties
Ski 26 Properties
Berkshires 3 Properties
Courtyard 3 Properties
Econo Lodge Lee Great Barrington 3 Properties
Fairfield Inn 3 Properties
Fairfield Inn 3 Properties
Hampton Inn Suites 3 Properties
Hilton Garden Inn Pittsfield 3 Properties
Holiday Inn Club Vacations Oak N Spruce Resort 3 Properties
Holiday Inn Express Hotel Great Barrington Ihg 3 Properties
Howard Johnson 3 Properties
The Hill 3 Properties
The Williams Inn 3 Properties
See More Complexes

Frequently Asked Questions About The Berkshires?

What are the top vacation rentals in The Berkshires?

When organizing your trip to The Berkshires, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in The Berkshires. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in The Berkshires?

Uncover 119 vacation rentals boasting private pools near The Berkshires. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in The Berkshires are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in The Berkshires. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in The Berkshires?

Discover the ideal vacation rental in The Berkshires with SunSki Resorts™. We provide an extensive selection of over 1645 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to The Berkshires.

Nearby Neighborhood (1) 
Neighborhood Property Count
Sherwood Forest Vacation Rentals in Massachusetts 69

People Also Ask

There are 1645 The Berkshires, MA Vacation Rentals

Recently Booked Vacation Rentals in The Berkshires