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

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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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The exterior of the farmhouse is framed by vibrant autumn foliage, featuring a combination of orange, yellow, and red leaves. A gravel driveway leads to the entrance, with a spacious porch that enhances the inviting appearance of the home.

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.

A two-story dark blue house is seen surrounded by trees, featuring large windows with white shutters. A garage is positioned to the left, and a wooden staircase leads up to the front entrance, framed by a gravel path and natural greenery.

Apartment in Canaan

4.29 out of 5 average rating, 7 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

A loft area features a wooden pitched ceiling and warm wood paneling. A deep U-shaped lounge is arranged with patterned cushions. A small coffee table holds a bowl of oranges and books. Natural light enters through a window, illuminating the cozy seating arrangement.

Hotel room in Hillsdale

Little Cat Lodge -Two Bedroom Deluxe - West Suite

Our most expansive Suite totaling 1343 sq. ft., & perfect for a large family getaway. Located on the 2nd floor of the Main House, the West Suite sprawls across 2 floors Downstairs includes one bedroom (Queen), a powder room, and bathroom with walk-in shower, large soaking tub, double vanity, and water closet, all adjacent to an open living room with kitchenette. In the loft upstairs you can find another bedroom (King), a writing nook with turntable, and deep U-shaped lounge. Sleeps up to 8.

A rustic wooden sign hangs from a post, displaying the name 'Knoll Rock' and a pineapple emblem. Lush greenery and trees frame the scene, with a gravel road leading away from the sign, suggesting a peaceful, natural setting.

Guest suite in Canaan

5 out of 5 average rating, 9 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

The Washington Room features warm wood walls and soft natural light from windows dressed with lace curtains. A large bed is adorned with a cozy quilt, while a vibrant floral lamp and decorative chair provide inviting accents.

Private room in Sheffield

4.93 out of 5 average rating, 44 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.

Home in Ancramdale

4.8 out of 5 average rating, 10 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.

Home in Athens

5 out of 5 average rating, 4 reviews

Hot Tub with Pond-front Firepit and Hiking Upstate

Welcome to your dream getaway . Sleepy Hollow offers a variety of premium amenities, including beach access, multiple swimming pools, tennis courts, basketball courts, ensuring there’s something for everyone to enjoy. Additionally, the charming towns of Hudson and Catskills are just 15 minutes away and is renowned for its vibrant culinary scene, art galleries, and antique shops. Albany, New York’s capital, is a short 30-minute drive from the property.

Top guest favorite

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

4.97 out of 5 average rating, 356 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!

A well-appointed bedroom features a spacious bed with layered bedding, flanked by windowed walls allowing natural light. A wooden dresser and a seating area with a coffee maker provide convenient amenities. The adjoining bathroom is visible through a doorway, enhancing overall functionality.

Hotel room in Hillsdale

Little Cat Lodge - 2 Bed 2 bath Suite - East Suite

Located on the 2nd floor of the Main House, the 732 sq. ft. East Suite blends the old world rustic charm of a chalet with modern amenities. A sunrise view of the mountain can be had from the 2 bedrooms, 1 with King bed, 1 with Queen bed. The 2 bathrooms - 1 with bathtub shower and 1 with vertical shower - and seating area with sectional sofa and a large TV that’s great for movie watching round out the cabin vibes. Sleeps up to 5.

Superhost

The bedroom features a spacious bed with a plaid blanket and decorative pillows, including one with a bear motif. A wooden bench sits at the foot of the bed. A dining table with two chairs is positioned near a window adorned with white blinds.

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