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

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

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

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

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Home in Canaan

5 out of 5 average rating, 11 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.

Private room in Claverack

4.92 out of 5 average rating, 107 reviews

Peaceful Solar Home

Our one-story, round house is nestled in a "holler" on a quiet dirt road, surrounded by an active farm landscape (all organic), woods & waterways. We are just a short drive to High Falls, Won Dharma Center, or Warren St in Hudson. A drive of 20-30 minutes will get you into the Berkshires. Our guest room has a single twin bed and so we just host solo folks. We are off the power grid and solar-powered. Before I accept, it's helpful for me to know the nature of your plans to be here. Thanks!

Guest favorite

Home in Germantown

4.96 out of 5 average rating, 298 reviews

Modern Country Cottage, Views, Trails, Fireplace!

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New appliances. Total privacy, high ceilings, hand plastered walls, antique wood doors. Glass doors open onto 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! For more photos at @martinasplaces at insta/gram

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 favorite

Private room in Sheffield

4.93 out of 5 average rating, 41 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 favorite

Home in Tivoli

4.98 out of 5 average rating, 65 reviews

Dramatical sited in trees , walk to town

September light Down a long driveway, our Architect designed Hudson Valley 9 acre compound is private yet minutes to the village of Tivoli; our "passive haus" is surrounded by decks, wild pollinator's gardens and a grove of 100 year old oaks. Flooded with sunlight , the house offers the best in modern building science, cool in the summer, warm in the winter. This is not a party house but a house for friends and families to enjoy. Monthly and weekly discounts offered. Just ask

Guest favorite

Guesthouse in Tivoli

4.93 out of 5 average rating, 153 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.

Home in Ancramdale

4.86 out of 5 average rating, 7 reviews

Family-Friendly Home in Ancramdale

It's our family weekend home, a place that has been exclusively enjoyed by our immediate family. We're excited to extend a warm welcome to other families who can appreciate the space, nature, and amenities our home has to offer. Nestled in a private lake community shared by only a handful of families, our home offers a unique opportunity to experience lake activities, hiking, biking, skiing, and more.