Ski-in/Ski-out holiday rentals in Columbia County

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Columbia County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Home in Canaan

5 out of 5 average rating, 13 reviews

Knoll Rock House (3B/3B) - Best of the Berkshires

Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has recently undergone total restoration. Knoll Rock House offers a wonderful combination of historic features combined with state-of-the-art comforts and amenities. Set on 4 tranquil acres, and close to Tanglewood and all the cultural and leisure activities the Berkshires and Hudson Valley region has to offer, this is the perfect place for a relaxing getaway or memorable vacation.

Flat in Canaan

4.4 out of 5 average rating, 5 reviews

3 Bedrooms and a Queechy Lake

Our private road will lead you to this unique home where your family will fall in love with our Canaan NY home which overlooks pristine Queechy Lakes Breathtaking water views, serene surroundings, and luxurious comfort in the Spring and Summer. In Autumn, fall foliage and untouched snow in the wintertime is perfect a long weekend or extended stay. Enjoy Adams Point Beach and Perfect for skiers; Bosquet Mountain, Jiminy Peak, Butternut & Catamount Centrally-located .. to Chatham and Pittsfield

Guest suite in Canaan

5 out of 5 average rating, 8 reviews

Knoll Rock Studio - Best of the Berkshires.

Located in Canaan, NY, less than a mile from the Massachusetts border, this is the 900 sq ft studio wing of a 1700s farmhouse that has recently undergone total restoration. Knoll Rock Studio offers a large living area and large bedroom with all comforts and amenities. Set on four tranquil acres, and close to Tanglewood and all the cultural and leisure activities the Berkshires and Hudson Valley region has to offer, this is the perfect place for a relaxing getaway or memorable vacation.

Guest favourite

Private room in Sheffield

4.93 out of 5 average rating, 42 reviews

Sheffield Lodge - Washington Room

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

Guest favourite

Home in Ancramdale

4.89 out of 5 average rating, 9 reviews

Family-Friendly Home on a Private Lake

Come and enjoy summer swimming, kayaking, hiking, cycling and relaxation in nature! This family weekend home, previously exclusively enjoyed by our immediate family, is now available for others who appreciate its space, nature, and unique amenities. Nestled in a private lake community shared by only a few families, our home offers a rare opportunity to enjoy lake activities, hiking, biking, skiing, and more. It’s the perfect retreat for families seeking both adventure and tranquility.

Guest favourite

Home in Tivoli

4.99 out of 5 average rating, 67 reviews

Modern House, Wild Gardens, Peaceful Creeks

Nestled at the end of a long private driveway, our architect-designed Hudson Valley compound offers a peaceful retreat on nine secluded acres - just minutes from the charming village of Tivoli, home to beloved general stores, restaurants, and some truly amazing ice cream. Surrounded by wild pollinator gardens, a grove of century - old oaks, and the tranquil flow of Stony Creek, the house is designed to immerse you in nature while providing the comfort and elegance of modern living.

Guest favourite

Home in Germantown

4.97 out of 5 average rating, 345 reviews

Private Cottage/Mountain Views/Trails/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Guest favourite

Guest house in Tivoli

4.91 out of 5 average rating, 184 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

Superhost

Hotel room in Hillsdale

Ultimate Mountain Access Catamount Ski In/Out

Welcome to Catamount! Just steps away from the slopes, our rooms feature exceptional views, unparalleled access, and ideal privacy. You'll also be in the perfect jumping off point for further adventures in Hudson, NY and the rest of the Hudson Valley, or to Great Barrington, MA and the Berkshires beyond. Welcome to the best kept secret in the New York Berkshires!

Superhost