Condo vacation rentals in Berkshire County

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Top-rated condo rentals in Berkshire County

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Guest favorite

Condo in Hancock

4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

Superhost

Condo in Hancock

4.85 out of 5 average rating, 39 reviews

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

Guest favorite

Condo in North Adams

4.84 out of 5 average rating, 19 reviews

Charming downtown Condo!

Overlooking the Historic Eagle Street district in downtown North Adams, this centrally located, 2nd floor 330 sq ft unit just got a facelift! New paint throughout, furnishings, etc.... Sleeps 2 people (queen size bed) but we also have a fold out chair in the office area as well. Fully equipped eat in kitchen and 3/4 bath. 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.

Guest favorite

Condo in Hancock

4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Condo in Hancock

4.9 out of 5 average rating, 10 reviews

Ski-in/Ski-Out on Jiminy Peak

Jiminy Peak Mountain Resort is the perfect Berkshire get away surrounded by cultural attractions and with skiing, mountain biking, snow shoeing, mountain coaster, ropes course and MORE right on property! For an easy convenient trip once you arrive you will not have get back into your car. Jiminy Peak has everything you need on property bar/restaurants, ski/ snowboard shop, general store, ski/snowboard and snowshoe equipment rentals, ski/snow lessons and school, day care, souvenir shop.

Superhost

Condo in Hancock

5 out of 5 average rating, 4 reviews

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.

Guest favorite

Condo in North Adams

4.96 out of 5 average rating, 71 reviews

Newly renovated 2BR on historic Eagle Street.

Enjoy the comforts of a newly renovated, quiet and centrally located apartment on historic Eagle Street. Visit the unique boutiques of downtown North Adams, Mass MOCA just a few blocks away, or take a short drive to many of the cultural attractions of the northern Berkshires. One flight of stairs takes you to a 2 bedroom (+ sofa bed), 1 bath apartment featuring vaulted ceilings, a full kitchen, laundry room and tons of light.

Superhost

Condo in Hancock

4.91 out of 5 average rating, 23 reviews

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.

Guest favorite

Condo in Hancock

4.92 out of 5 average rating, 65 reviews

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.

Condo in Great Barrington

4.85 out of 5 average rating, 41 reviews

Gem of the Berkshires, walkable to lake & downdown

My place is located in the heart of the Berkshires. Near Tanglewood and Jacob pillow. Walkable to the lake & downtown we you can find large variety of great restaurants. You’ll love my place for it's stunning view and spacious design. Perfect for families / groups celebrating reunions, weddings, & special occasions. Favored by couples, friends, & families with children. Equipped with gas grill, & kayaks/canoe.

Guest favorite

Condo in Hancock

5 out of 5 average rating, 8 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

Nestled in the Berkshire Mountains at the base of Jiminy Peak Ski Mountain, this resort takes "weekend getaway" to a whole new level! No matter what time of year that you choose to visit, you will never run out of things to do. Enjoy clean and spacious rooms and amenities that include an indoor/outdoor swimming pool, sauna, convenience store, massage services and laundry facilities.

Guest favorite

Condo in Lenox

4.9 out of 5 average rating, 77 reviews

Heart of Lenox!! - Renovated downtown apartment

Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road you will find the historic Red lion Inn in Stockbridge or Norman Rockwell Museum.