Condo vacation rentals in Berkshire County

Jiminy Peak Country Inn 1 Bedroom Suite

A privately owned, older unit within Jiminy Peak's Country Inn. Located in the Berkshires, the inn is at the base of the ski slope. This unit is on the 1st floor of the last building which means you can ski to your doorstep if there's lots of snow (harder getting to the lift) . A locker room is at the end of the building to secure your equipment (key provided). The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and seasonal restaurants. Come enjoy the mountain!

Downtown Condo - walk to MoCA

New owners but same great location! Overlooking the Historic Eagle Street district in downtown North Adams, you'll find this centrally located, 330 sq ft. condo. Sleeps 2 people (full size bed and fold out futon), Fully equipped eat in kitchen and 3/4 bath. You shouldn't need much more for your stay here in North Adams. Please note: This condo is located on the 2nd floor. Due to the antique nature of the building, there is no handicap accessible entrance, and the stairs are steep and narrow.

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, and be at Jiminy Peak - This condo is for you - right in the heart of Country Village. This Stylish 2BR country Condo w AC is fully updated and comes with parking in front and full access to the Country Inn Amenities ( Fitness, pools, hottub, Tennis etc). This large 900 sq ft condo features country decor, & sleeps up to 7 with a queen, two bunk beds, pull out Trundle, and Full Bed.

Tranquil Lakeside Escape in the Berkshires

Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. Perfect for families or small groups, this peaceful escape offers a pond-view deck, a full kitchen, fireplace, and access to resort amenities like indoor/outdoor pools and a fitness center. Explore hiking trails, waterfalls, and cultural gems nearby. Unwind with stunning views, cozy interiors, and a wealth of year-round outdoor recreation right at your doorstep.

Berkshires Resort with Pools - Lg 1BD - Sleeps 4

Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities; Lounge or swim in the indoor or outdoor pools. Go skiing, hiking, biking, horseback riding or enjoy a tranquil day with a soothing soak in the outdoor hot tub. A fitness center is available for our more active guests. Nearby you’ll find many opportunities to enjoy the arts; Hancock Shaker Museum, Tanglewood, the Clark Institute and Museum and more!

Wyndham Bentley Brook

This premier Berkshires destination resort is located at the base of the ski slopes of Jiminy Peak Mountain Resort. After a day of skiing, snowboarding, hiking and other seasonal activities, return to your spacious two-bedroom resort suite designed for maximum rest and relaxation with a kitchen and spacious living/dining area. The resort's heated indoor and outdoor pool, game room, sauna, and activities center are sure to please.

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Luxury Apt in Downtown Great Barrington

Luxury 1 bedroom apartment in a brand new building located in downtown Great Barrington. You don’t need a car, just pack your suitcase and take the bus from NYC or Boston. Walk downstairs for groceries or lunch at the Berkshire Co-op Market, restaurants, shopping, theatre, and hiking. Located close to ski resorts (Butternut Ski resort 7 minutes away & Catamount resort 14 minutes away).