Waterfront holiday rentals in Columbia County

Hudson Holidays!

Luxury Hudson Rental, in a unique historical facility! Perfect for first time visitors. Among the city's largest private, open-plan homes. Often accommodates VIPs & Celebrities. Loft-Style layout hearkens to Soho living. Restaurant-scale kitchen fosters entertaining. Historic preservation adds to the experience, and "Flex Space" allows for multiple configurations: Dinners, Salon, Event, etc. A rare experience in a most unique Hudson facility. (A/C upgraded 2025.) Extra Guest Fee $50. Pets $50.

Modern Mid-Century Cottage - Skiing @ Catamount

Let all your worries fade away in this beautifully remodeled modern cottage! Our 3 bedroom, 2 bath can sleep 8 adults in 2 Queen Beds, 2 Twin Beds and a Queen Sleeper Sofa. Relax by the fire pit out back or take out our 2 two person Kayaks and enjoy the lake in the summer, visit Catamount Ski Resort or other nearby ski mountains in the winter. The large, custom dinner table seats 8 comfortably with lots of room to hang, play games, watch movies and more. Guests must be 25 years old to rent.

Stylish Studio, Catskills Views, WalkingTrails

Sophisticated large studio with gorgeous light and Catskill Mountain Sunsets. Formally an artist studio, the space features a luxurious bathroom with a glass walled shower. The modern well equipped kitchen has a full sized refrigerator, microwave, toaster, cooktop, outdoor grill Private deck for outdoor lounging and dining Set on a private park like 65 acres, directly on the Hudson River with walking trails Germantown 5 minutes. 10 minutes to Tivoli, Hudson or Bard College.

Rushing Rapids Cottage – a birdwatcher's paradise

Complete renovation with privacy. Rural mill worker's cottage is upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a rural paved road and AHET Rail Trail. Minutes to Hudson and Kinderhook. You may see Carolina Wrens, Cardinals, Chickadees, Woodpeckers, Goldfinches and Hummingbirds. The creek to the front attracts Bald and Golden Eagles, Osprey, Blue Herons, Red Tail Hawks, Ducks and Geese. ABSOLUTELY NO PETS ALLOWED.

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Kayak, pet a Highland cow, have dinner in Hudson!

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount. Cozy wood burning stove as well as outdoor fire pit. Ask about a farm visit!

Lakeview Bungalow w/ Hot Tub, Fireplace & Skiing

Relax and recharge at this charming 2BR lakeview bungalow in Copake Lake, NY. Just steps from the water, it features a private deck, firepit, cozy fire stove, two paddle boards, and a brand-new hot tub. Enjoy hiking, boating, skiing at nearby Catamount Mountain, winter walks around the lake, or simply unplugging. Close to Hudson and Great Barrington with easy access to trails, dining, and more — a stylish year-round retreat for couples, families, or friends.

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

Riverside Retreat on the Hudson - Modern Cottage

Welcome to the Riverside Retreat on the Hudson, a modern renovated cottage located directly on the Hudson River! Enjoy the beautiful panoramic views from the comfort of the house or in the Adirondack chairs on the patio. Secluded and serene, yet minutes away from downtown Catskill (5 minutes) and Hudson (15 minutes). Hunter and Windham are 30 minutes away for hiking and skiing! We are so excited to share this very special place with you!

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

Welcome to Casa Bartolo, Your Oasis on the Hudson!

Why book a hotel when you can enjoy a charming, private 2-bedroom suite with breathtaking views of the Catskill Mountains, Hudson River, and stunning sunset! This tranquil retreat offers: Private Entrance, Private Bathroom, Kitchenette, cedar soaking tub & easy parking. Wake up to the sunrise and enjoy a cup of Nespresso or tea. Whether you want to relax, walk, jog, bike, meditate, or simply unwind, this is the perfect escape.

Lakefront +pets +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.