Berkshire Timeshare: Top 5 Resorts

Oak n' Spruce Mini Golf Course

Thinking about buying a timeshare in the Berkshires? We’ve ranked the top 5 Berkshire timeshare resorts to help you decide where to buy. Straddling western Massachusetts and northwestern Connecticut, the highland region known as the Berkshires is a cultural art haven and popular family vacation destination. As such, it hosts plenty of top-tier timeshare resorts, from Vacation Village in the Berkshires to Oak n’ Spruce to Berkshire Mountain Lodge and beyond. You’ll find all these incredible Berkshire timeshare resorts and more in our low-priced, easy-to-navigate resale marketplace. But first, check out our ranking of the top 5 resorts in the Berkshires!

How We Picked Our Top 5

With majestic mountain scenery, abundant recreation opportunities, and a vibrant arts scene, the Berkshires make a great vacation destination for any traveler. However, what determines a great Berkshire timeshare resort is more subjective. In the end, it all depends on your needs. For example, what might seem like a relaxing vacation lifestyle to one vacationer might seem like a sedentary vacation lifestyle to another.

With that in mind, we’ve picked 5 Berkshire timeshares that suit a range of needs, from the best all around to the most family-friendly, to the most romantic, the best for skiing, and the most private. So, without further adieu and in no particular order, here are the top 5 timeshares in the Berkshires.

Vacation Village in the Berkshires – Best All Around Berkshire Timeshare

Located in Hancock, Massachusetts, less than an hour from the Albany International Airport, Vacation Village in the Berkshires boasts an unbeatable location that puts the best of the Berkshire Mountains at your command. Enjoy a well-rounded vacation adventure no matter what time of year you decide to travel. Like to ski? Open seasonally, the nearby Jiminy Peak ski area boasts a range of slopes and cross-country trails catering to skiers at all levels of experience. Want to get out of the cold? Near Vacation Village, you’ll also find tons of museums, art galleries, and entertainment venues to explore during ski season. Prefer to vacation in the warmer months? Golf, fishing, hiking, and horseback riding are all popular ways to enjoy the natural beauty of the Berkshires.

Vacation Village in the Berkshires Amenities

Back on-site, Vacation Village in the Berkshires offers even more ways to round out your vacation itinerary. Enjoy all-season swimming with indoor and outdoor pools. Or, drop your kids off at the game room and treat yourself to some well-earned pampering at the full-service spa. A state-of-the-art fitness center lets you keep up with healthy habits, while shared laundry facilities let you keep up with the wash.

Vacation Village in the Berkshires Accommodations

After a long day enjoying the resort’s top-notch amenities and nearby Berkshire attractions, one- and two-bedroom timeshare villas invite you to unwind and recharge with all the comforts of home, such as a full kitchen, full bathrooms, a fireplace, and more. And what better way to start the next day than with a cup of coffee on your private patio or balcony overlooking the Berkshire mountains?

Browse Now: Vacation Village in the Berkshires!

*Resort Fee: $50 per reservation

Holiday Inn Club Vacations Oak n’ Spruce Resort – Best Berkshire Timeshare Resort for Families

The Berkshire Mountains are a top family vacation destination. And Holiday Inn Club Vacations Oak n’ Spruce Resort might just be the best family vacation timeshare resort in the Berkshires. Your little saplings can stay rooted to the resort and never run out of fun things to do. On-site amenities include an indoor pool, two outdoor pools, an 18-hole mini golf course, sports courts, an arcade, and more!

Holiday Inn Club Vacations Oak n’ Spruce Resort Accommodations

Accommodations at Oak n’ Spruce Resort range from one to three bedrooms, offering families of all sizes plenty of legroom. Enjoy all the comforts of home and more, from full kitchens where you can make homecooked meals to fully furnished balconies and terraces where you can dine surrounded by sweeping mountain views.

Oak n’ Spruce Nearby Attractions

Holiday Inn Club Vacations Oak n’ Spruce Resort is ideally located for exploring the Berkshires. Family-friendly activities abound in this vacation hotspot. Head to nearby Brodie Mountain, Butternut Basin, or Jiminy Peak for skiing and snowboarding in the winter. Vacationing in the spring or summer? From boating to fishing to hiking to watersports such as windsurfing and water skiing, you’ll find no shortage of ways for the whole family to enjoy the countryside beauty of the Berkshire Mountains. Fall is also a great time to visit the Berkshires, as the fall foliage sets the mountains ablaze in color. And no matter what time of year you decide to vacation, you’ll find plenty of shopping opportunities in the Berkshires. Find unique treasures made by local artists, or gear up with outdoor activity equipment at one of the many area outfitters.

Browse Now: Holiday Inn Club Vacations Oak n’ Spruce Resort!

*Resort Fee: $10 per night

Wyndham Bentley Brook – Best Skiing

Love to ski in the winter? Hunkered right at the foot of Jiminy Peak and with an on-site lift straight to the top of the mountain, Wyndham Bentley Brook is the ultimate Berkshire timeshare for ski enthusiasts. Jiminy Peak boasts a variety of runs ranging from easy to expert, so don’t worry if you’re just starting out. There’s even a ski school if you want to learn how to ski or brush up on your skills.

Wyndham Bentley Brook Nearby Attractions

Of course, you don’t have to love skiing to love Wyndham Bentley Brook. The Berkshires is a cultural art haven, offering no end of historical museums and unique artistic experiences. Visit the Norman Rockwell Museum to see how one artist captured and inspired the American Dream with his illustrative vision. Visiting in the summer? Tanglewood in the Berkshires is the summer home of the Boston Symphony, one of the foremost symphonies in the world! Other unique cultural experiences include plays at the Williamstown Theater, The Hancock Shaker Village living museum, as well as art museums like MASS MoCA and Clark Art Institute.


Unit types at Wyndham Bentley Brook include studio suites and one-to-two-bedroom villas. Studios sleep up to four guests and include Wi-Fi, while one- and two-bedroom villas sleep eight guests and come with a patio or balcony. All units feature a fully equipped kitchen, spacious living and dining area, queen beds, and queen pull-out sofas for extra sleeping space.

Browse Now: Wyndham Bentley Brook!

*Resort Fee: $95 per reservation

Berkshire Mountain Lodge – Best Resort for Couples

Want to take that special someone on a romantic getaway to the Berkshires? Berkshire Mountain Lodge is the top Berkshire timeshare resort for couples. At 850 sq. ft., the cozy one-bedroom suites are perfectly proportioned for honeymoons, anniversaries, or any other romantic occasion. Plus, suite amenities include fully equipped kitchens, spacious living areas, elegant dining areas, and soaking tubs. So you’ll have everything you need for a relaxing night in.

Berkshire Mountain Lodge Amenities

Outside your unit, you’ll find even more ways to spend quality time as a couple. Head down to the indoor pool for an impromptu night swim, then warm back up with a long soak in the hot tub. Looking for something that shows a little more forethought? Prepare a gourmet lunch in your fully appointed kitchen and enjoy a picnic for two at the on-site picnic area.

Berkshire Mountain Lodge Nearby Attractions

Of course, what romantic getaway would be complete without a date night here or there? You’ll find lots of unique date options near Berkshire Mountain Lodge. Tour the estate of writer Edith Wharton, the first woman to receive the Pulitzer Prize. See the Boston Symphony perform in their summer home, Tanglewood. Or, peruse one of the many nearby art galleries, such as Schantz Galleries Contemporary Glass, Tom Fiorini Sculpture Yard, or the WIT. And after you’ve had your fill of the arts, fill your bellies at one of the area’s many fine dining establishments, such as Mazzeo’s Ristorante, District Kitchen and Bar, or Trattoria Rustica.

*Resort Fee: $20 per reservation

The Ponds at Foxhollow – Best Berkshire Timeshare Resort for Getting Away From it All

Sheltered by stately pines, studded with jewel-like ponds, and framed by the Berkshire Mountains, The Ponds at Foxhollow is the best Berkshire timeshare resort for getting away from it all. The resort resides on a 223-acre estate and offers endless opportunities for outdoor recreation. When you check-in, load up on outdoor activity equipment at the front desk. Then, after you unpack, head out to explore the secluded estate. On the grounds, you’ll find hiking paths, cross-country skiing trails, and even canoe rentals for the ponds. But hey, maybe enjoying nature just isn’t in your…nature. Fear not, because you’ll find plenty of more civilized amenities at The Ponds, too. Tuck into a good book at the library, lounge by the indoor or outdoor pool, melt away stress at the hot tub or sauna, or work up a sweat on the sports courts or at the fitness center.


The condominium-style accommodations at The Ponds at Foxhollow come in options for one or two bedrooms and overlook the main pond. All units come equipped with a fireplace, bar area, and TV with a DVD player. In addition, the two-bedroom condos feature a sitting-area loft and a full second bathroom.

Nearby Attractions

While The Ponds at Foxhollow is undoubtedly secluded, it isn’t isolated. In fact, owners and guests enjoy convenient access to everything the Berkshires has to offer. Recreational activities abound, from cross-country and downhill skiing in the winter to hiking, biking, and boating in the warmer months. Moreover, The Ponds at Foxhollow is just minutes from all of the Berkshires’ best cultural and artistic attractions. Help yourself to a slice of Americana at the Norman Rockwell Museum. Or, catch a live performance at Tanglewood or the Williamstown Theater. In short, whatever your preferred medium, you’ll find no end of creative fulfillment and inspiration in this cultural art haven.

*Resort Fee: $45 per reservation

Buy a Berkshire Resort Timeshare With Fidelity Real Estate

Fidelity Logo

So, you want to make the Berkshires your official vacation destination? With a Berkshire resort timeshare, you can have a home away from home in the Berkshire Mountains and make vacation memories year after year. And with Fidelity Real Estate, you can have it for less.

Fidelity Real Estate is your premier vacation timeshare resale marketplace, with a large selection of Berkshire’s timeshares, as well as licensed real estate agents to facilitate your purchase. So what are you waiting for? Browse our inventory of vacation timeshares for sale in the Berkshires now! Need help? Then give our agents a call at 1-800-410-8326.

  • By submitting, you agree to our Terms and Conditions and our Privacy Policy
  • This field is for validation purposes and should be left unchanged.

Join The Discussion

Compare listings