Chalet holiday rentals in Columbia County

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Top-rated chalet rentals in Columbia County

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Guest favourite

Chalet in Athens

4.88 out of 5 average rating, 56 reviews

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

Chalet in Hillsdale

4.75 out of 5 average rating, 32 reviews

Contemporary chalet on 11 acres

Charming chalet situated on the top of a wooded hillside, with a long, private driveway and 11 acres of woods with pond and nature trails. Short drive to Hudson & Great Barrington. Open plan living area has large sectional, stunning morning light, Hue lighting + hip decor. Kitchen has new stainless steel appliances. Two bedrooms upstairs, and TV room/office lead to expansive, private deck with hot tub and furniture for relaxing and enjoying nature. Downstairs lounge has a bar, couch, TV and gym.

Chalet in Athens

New place to stay

Brand New Lakefront Retreat in the Catskills!

Perched upon a serene cove of Sleepy Hollow Lake, we invite you to escape the daily grind & unwind at the Gray Owl Lodge. Our spacious 4 BR 3 BA home (sleeps 10) offers breathtaking lake views from almost every room. Experience lake life with our kayaks, paddle boards, canoe, & water trampoline. Sit back & relax on our wraparound deck, cozy up in the cabana by the water, lounge in the hammock on our pebble beach, or toast s'mores at our firepit. Only 15 mins to Hudson & 35 mins to ski resorts!

Guest favourite

Chalet in Great Barrington

4.96 out of 5 average rating, 74 reviews

Berkshire "Zen" Cottage

"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.

Chalet in Hillsdale

4.86 out of 5 average rating, 64 reviews

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!

Top Guest favourite

Chalet in Copake

4.98 out of 5 average rating, 65 reviews

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.

Guest favourite

Chalet in Athens

5 out of 5 average rating, 13 reviews

Lakefront Chalet-Spacious | Dock-Kayaks |Guest Fav

90+ 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!

Guest favourite

Chalet in Leeds

4.96 out of 5 average rating, 145 reviews

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!

Top Guest favourite

Chalet in Canaan

5 out of 5 average rating, 13 reviews

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 offers unparalleled panoramic sunset views of the mountains and rights to Queechy Lake. On 7 private acres the Chalet offers the unique opportunity to disconnect from our busy lives and reconnect with ourselves, family, or friends. Imagine starting the day with sunrise yoga on the enormous mahogany deck and ending it with sunset cocktails on the same deck.

Chalet in West Stockbridge

4.95 out of 5 average rating, 41 reviews

Secluded Mountain Home 7min from Great Barringtom

Sunlight filled, 3 Bedroom, open-plan home in a quiet mountainside location, but only 7 mins from Great Barrington, 13 mins to Lenox & Tanglewood. Cathedral ceilings, modernly furnished, open, modern kitchen and dining. Screened-in porch for outdoor dining. Enjoy mountain views with endless windows and deck. Fire pit for summer s'mores. Well positioned to embrace the great outdoors all year round - with swimming, hiking, boating, skiing, shopping, etc., ... all within 10 minutes drive.

Chalet in Canaan

4.57 out of 5 average rating, 69 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

Welcome to Your Perfect Retreat Escape to a serene 15-acre estate in the heart of the Berkshires, where relaxation and renewal are effortless. Designed for peaceful getaways or intimate group retreats, this tranquil haven offers thoughtfully curated accommodations, Private tennis court and pool. Salt water hot tub. 4 bedrooms with queen beds, and expansive landscapes. Immerse yourself in nature, unwind, and gather with loved ones to create lasting memories in an unforgettable setting.

Guest favourite

Chalet in Athens

4.88 out of 5 average rating, 117 reviews

Waterfront Lake Home, close to Hunter & Windham

Located w/in the Sleepy Hollow Lake community, adjacent to The Hudson River, offering an unrivaled location to experience all that Hudson has to offer. The quaint community of Sleepy Hollow is 30 minutes from Hunter Mountain & Wyndham Mountain, and 20 minutes from Hudson. The community enjoys its own beach, boat ramp, tennis courts, bocce ball court, 2 swimming pools (seasonal), outdoor full-size basketball court, a baseball/softball field, volleyball court, and a golf driving range.