Condo vacation rentals in Berkshire County

Find and book unique condos on Airbnb

Top-rated condo rentals in Berkshire County

Guests agree: these condos are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favourite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 62 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!

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.
Condo in Hancock
4.61 out of 5 average rating, 155 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 favourite
A spacious living area features a light-colored sofa and an accent chair, with a coffee table centered on a patterned rug. Shelves display decorative items, while a television is mounted above a stone fireplace. Natural light enters through windows accented with blue curtains.
Condo in Hancock
4.91 out of 5 average rating, 11 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.

Superhost
A cozy living area features a comfortable sofa grouped with an armchair and a coffee table. A large window allows natural light to illuminate the space, while curtains frame the view. A television is positioned nearby, enhancing the room's functionality.
Condo in Hancock
4.82 out of 5 average rating, 11 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.

A winter scene depicts a snow-covered building with a sloped roof. A large evergreen tree stands in the foreground, and snow blankets the ground. The distant ski slope is visible on the mountain, showcasing a winter recreational setting.
Condo in Hancock

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

An outdoor view of a lively resort features a large swimming pool surrounded by sun loungers, with families enjoying the water. Nearby, tennis courts are visible, and a mini-golf course is positioned in the foreground, blending seamlessly with the natural landscape.
Condo in Lee
4.82 out of 5 average rating, 38 reviews

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.

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.
Condo in Lenox
4.7 out of 5 average rating, 10 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
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
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 favourite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock
4.9 out of 5 average rating, 72 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.

Guest favourite
The living area features a comfortable seating arrangement with a dark sofa and a brown chair, complemented by a large mirror. A dining table for four is positioned near a window, allowing natural light to illuminate the space. A soft area rug enhances the room's warmth.
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).

The exterior of the resort is highlighted by a wooden gazebo surrounded by lush greenery. The three-story building features gabled roofs and multiple balconies, with warm lights illuminating the windows during twilight.
Condo in Hancock
4.89 out of 5 average rating, 9 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.

Top guest favourite
A modern kitchen is visible, featuring stainless steel appliances and ample storage cabinets. A dining table set for four is in the foreground, complete with glassware and decorative green accents. Natural light fills the space, highlighting the open floor plan that leads into the living area.
Condo in Lenox
4.9 out of 5 average rating, 84 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.

Popular amenities for Berkshire County condo rentals

Destinations to explore