Chalets als Ferienunterkünfte 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.

Secluded Mountain Home 7min from Great Barringtom

Sunlight filled, 3 Bed, 2.5 bath, modern, open-plan home in a quiet mountainside location, only 7 min from Great Barrington, 13 min to Lenox & Tanglewood. Cathedral ceilings, modernly furnished, well equipped kitchen with dining for 10. Enjoy mountain views with endless windows, screened porch and deck sitting with the trees. Fire pit for s'mores. Embrace the outdoors in any season - with apple picking, leaf peeping, skiing, sledding, spas, shopping, swimming, hiking etc., all 10 min drive.

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.

Lakefront Chalet-Spacious| Hunter, Windham 45 mins

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!

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!

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.

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.

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 furniture for relaxing and enjoying nature. Downstairs lounge has a bar, couch, TV and gym.

Lowest Rates for Fall + Ski Chalet!

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!

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.

Spacious 5BR House w Sauna - Skiing

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.