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, 61 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!

Condo in Hancock

4.6 out of 5 average rating, 152 reviews

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!

Guest favorite

Condo in North Adams

4.91 out of 5 average rating, 35 reviews

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.

Top guest favorite

Condo in Hancock

5 out of 5 average rating, 5 reviews

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.

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.

Condo in Hancock

5 out of 5 average rating, 3 reviews

Ski Jiminy Peak - 1BD

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!

Superhost

Condo in Lenox

4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshires. With a scenic pond view and surrounded by breathtaking mountains, this charming unit is perfect for couples or small families seeking tranquility. Enjoy a fully equipped kitchen, warm fireplace, and access to indoor and outdoor pools, along with endless nearby hiking trails and cultural activities. Your perfect getaway awaits in beautiful Lenox, MA.

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, 85 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.

Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 71 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

5 out of 5 average rating, 9 reviews

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).

Top guest favorite

Condo in Lenox

4.9 out of 5 average rating, 81 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.