Condo holiday rentals in Berkshire County

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!

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. Th

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!

the NAMA nest

Cozy Condo - Walking distance to MASS MoCA Welcome to North Adams, Massachusetts (NAMA), the heart of the Northern Berkshires! This one bed, one bath, sun-drenched cozy space is nestled in the iconic Flatiron Building, a unique, wedge-shaped landmark at the corner of Eagle and Church Streets, offering a one-of-a-kind architectural experience that blends 19th-century charm with modern downtown living. This cozy 330 sq ft nest is in the ideal spot for exploring NAMA, for short and long stays!

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.

Ski in & Ski out Deluxe Condo

Fantastic location at the base of Jiminy Peak Ski Resort. Fully equipped deluxe one bedroom condo with ski in and ski out access. Unit is on the third floor and has a fully loaded kitchen. Ski locker included on Main Floor. Lodging Accommodations: All-suites. Non-smoking, cable TV, WIFI Master bedroom: king-size bed, flat-screen TV. Living room: Queen-sized sleep sofa, flat screen TV, club armchair. Kitchen: Microwave, refrigerator, stove, toaster, coffee maker, dishes Bathroom

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.

Holiday Inn Club/ Oak and Spruce, Berkshires

This resort is the Holiday Inn Club at Oak and Spruce. The rooms have been greatly upgraded since I took these pictures. I own time shares here. It is a wonderful resort with so many amenities and the most perfect location, 15 minutes from Tanglewood, 10 minutes from center of Stockbridge. You can look it up for better photos on the web site. It is on a country road but near everything and well furnished and stocked. Reservations must be made at least 30 days in advance.

Vacation Village in Berkshires 12/28/25-1/4/26

7 Nights Dec 28, 2025 - Jan 3, 2026 at the beautiful Vacation Village in the Berkshires resort which is directly across the road from Jiminy Peak Ski Mountain. Unit comes complete with a fully stocked kitchen and everything you need for an enjoyable stay. This is a 7 night Sunday to Sunday rental. But you can check in and check out any day you like during that week. Resort is very clean with a large indoor pool and all amenities. Great for families!

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

4-season Berkshires retreat at the base of Jiminy Peak Mountain. PRIME ski-in/ski-out in winter, mountain adventure park in summer & fall. The 3BR/2BA JPeak Condo at JJ's Lodge sleeps 8–10 (2 Queens, 2 Fulls, 2 Twins) — steps from ski lifts, trails, Alpine Slide, mountain coaster & summit chairlift. Country Inn amenities (pool, hot tubs, gym, game room) open year-round. Village restaurants, fire pits, coffee shop & ski shop open ski season.

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).