Chalet holiday rentals in Columbia County

Large & Sunny Lakefront Home-kayaks/fire pit/games

Welcome to the perfect escape from the hustle of daily life. Our sunny 4 bedroom has plenty of space for the whole family. Relax and unwind enjoying our large backyard, deck, and lake views. The Sleepy Hollow lake community offers many amenities for your enjoyment, including 2 pools (seasonal), tennis courts, basketball courts, a swimming beach, and volleyball. Take a short drive into the charming towns of Hudson or Catskill NY and all they have to offer. Hunter and Windham Ski areas also nearby

Berkshire "ZEN" Chalet

"ZEN" Palace Chalet perfect spot to chill & relax after a day of exploring or skiing. SPACIOUS,secluded,quiet, great grounds -3 bdrm 2 ba with LUSH VIEWS endless windows. BEAUTIFUL exposed wood beams & ceilings throughout. Super family friendly. 5 min GREAT BARRINGTON, Butternut, Catamount, great food, nature trails, lakes, great shopping & farmer's markets. Close to STOCKBRIDGE,Tanglewood, Norman Rockwell Museum, Wheatleigh, Kirpalu,Canyon Ranch & HUDSON NY. Accessible knowledgable local host.

Natural Splendor: Forest Luxury Retreat

Discover your perfect retreat near the heart of the Berkshires! This charming house offers tranquility year-round. In autumn, vibrant golds surround you; in winter, enjoy the warm fireplace while snow dances outside. The game room features pool and ping pong tables, and the spacious family room has surround sound and a 65" TV. Relax on the screened porch or large decks, gather around the fire pit, and enjoy a baby grand piano. Close to top attractions and restaurants, your ideal getaway awaits!

Spacious Lakefront Chalet| Kayaks, Pools, Tennis

100+ Five Star Reviews - See Photos Reposting of existing AB&B property! 4+ years of 5 star hosting experience. Just 20 mins from Hudson NY via the Rip van Winkle bridge, this spacious lakefront chalet is comfortable, serene and loaded with amenities! The house is located on the lake with dock, kayaks, canoe and floats to get you out on the water. The Sleepy Hollow Lake resort community offers free amenities including pools, beach, tennis, pickleball and more. Just 30 mins from skiing as well!

Private upstate home nestled in the Hudson Valley

Recently renovated chalet-style home located in Copake New York 10 minutes from Copake Lake. Modern design meets country living. Centrally located with access to the Berkshires, Hudson, Catamount Ski Resort, Bash Bish recreation area and more! This 3-bedroom, 2-bath home sits on 3.5 acres of landscaped grounds with beautiful western views, garden patio, wrap-around deck, fire pit, modern amenities, central air, and outdoor games. Set back from the road, the property is private and secluded.

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

SRC-Hudson Valley/Berkshires Cultural Corridor

We welcome you to explore the magic of Sunset Ridge Chalet (SRC). Ideally situated in the Hudson Valley/Berkshires cultural corridor, SRC is a custom-designed mountain retreat that balances dramatic open-concept architecture with the cozy warmth of a family home. The Chalet offers unparalleled panoramic sunset views of the mountains and rights to Queechy Lake. 7 private acres offers the unique opportunity to disconnect from our busy lives and reconnect with ourselves, family, or friends.

Berkshires Vacation Home 6BR, 4 ski mtns, sunsets

A getaway at the edge of the Berkshires - family friendly, 4 ski mountains nearby, charming towns, fireplace, expansive deck, sunset views, private in-ground pool, BBQ, secluded, wooded, nearby lakes, hiking, Tanglewood for summer music and performance festivals. We've set up this vacation home for ourselves to enjoy, so you know we've put our hearts into it and are excited for you to create memories for a lifetime. The home is set up beautifully for families and groups of friends.

Low Spring Rates: Wood stove & screened porch!

Conway House: Conway House: Brand New Contemporary Chalet with 3 Bedrooms, 2.5 baths and sparkling river views! Sleeps 6 (8 max). Screened porch, central AC, propane wood stove, 2 HDTVs, 2 car garage with direct entry, propane grill, outdoor seating with solo wood stove, high speed internet, good cell service, washer/dryer, whole-house water filter for clean drinkable water, decks with river views and plenty of outdoor seating! All linens included. Pets considered. No Smoking, please!

Modern Mtn Chalet | 7m to Great Barrington & Ski

Modern mountain retreat with cathedral ceilings & forest views. Perfectly located for après-ski dinners for 10 or simply curling up by the fireplace. Enjoy a secluded mountainside setting just 7 mins to Great Barrington & Butternut Skiing, and 15m to Catamount or Lenox. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Adventure: Near spas, hiking, shopping & Tanglewood • Winter: 4WD/AWD recommended

Copake Lake chalet with indoor pool

Magical 3 acre property in Copake Lake with indoor pool. Perfect property for a relaxing and fun getaway with the family, friends, or professional retreats. The property has all the amenities you'll need. Very centrally located to hiking, skiing, farms, lake beaches, parks, towns (Hudson, Millerton, Catskill, Hillsdale, and Great Barrington are all 10-30 minutes away). There is magic to experience in every season at the Copake Lake Chalet.

East Chatham Spacious 5BR House Pool Sauna AC

Skiing nearby! 5BR retreat with sauna — perfect for large family or friends gatherings. Cook, connect, and unwind in rustic modern luxury. Nestled between the Hudson Valley and the Berkshires, this curated 5-bedroom estate features cathedral ceilings, panoramic forest views and a private sauna. Designed for rest and reconnection, with fast Wi-Fi and big-screen smart TVs for cozy holiday evenings. 20 min away from Jiminy Peak - skiing.