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The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

Enchanting Rustic Log Cabin in Heart of Catskills

This Hudson Valley rustic gem with its modern amenities provides a much-needed respite from city life. Located in the heart of the Catskills, a mere 1.5 hrs from NYC, it offers a chance to swim, hike, fish, hunt, play tennis, golf, visit farms, BBQ, watch hummingbirds, do yoga, pick strawberries & apples, go horseback riding, visit monuments, galleries, festivals & get away from it all! It's a true paradise for gourmet lovers with an incredible, fully stocked kitchen & farm-fresh foods nearby.

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

3Br Creekside Cottage on 130 acre forest w/ trails

Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm

The Cottage on Maple Grove Farm

Escape to this charming historic cottage on the border of artsy Pound Ridge and bucolic Bedford, NY. Maple Grove Cottage features a light-filled kitchen with French doors, beamed living room with working stone fireplace, a cozy bedroom with full bath and attached front sitting room. Enjoy your morning coffee sitting on the small deck outside the kitchen which overlooks a newly planted vineyard, watch the sun set over the adjacent field. Half mile from 5000 acre Ward Pound Ridge Preserve.

The Berkshires Mountain Terrace LUX Home Sleeps 7

Welcome to our peaceful Great Barrington sanctuary. 4 bedroom, 2.5 bathroom, 2 * lounge area home tucked away in an idylic mountain setting. 1 fireplace, sliding glass doors to both decks. Sunroom off the eat in kitchen, alfresco dining, separate formal dining room. 2 master bedrooms; 1 with en-suite; others with shared bathroom. Hidden escape with beautiful landscaping, mins from lake. Amazing location, close to Tanglewood, Jacob’s Pillow, Catamount, Great Barrington. All the Berkshires

Spacious Fam Retreat: Hot Tub, Fire Pit, BBQ

Escape to this family-friendly retreat! Cozy up by the fireplace or savor fresh air on the welcoming front porch. The large yard boasts a new hot tub, deck, BBQ, and fire pit—perfect for relaxing or entertaining. With a fully equipped kitchen, rec room, and laundry facilities, enjoy the comforts of home. This pet and kid-friendly haven is your perfect getaway for relaxation and fun. ✔ Spacious, Pet & Family-Friendly ✔ Hot Tub, Fire Pit, BBQ ✔ Wi-Fi, Large Yard

Modern Prefabricated Architectural Retreat

At Stonewall Hill, a modern prefab home set on 10 wooded acres, you can enjoy a cozy night by the fire in winter & cook a feast in the well-equipped kitchen or on the outdoor gas grill in summer. It has an open plan kitchen, living & dining space; a main bedroom w/ queen bed & ensuite bathroom; a 2nd bedroom that doubles as TV room w/ queen sofa bed & bathroom across the hall. 10 minutes to the HITS fairgrounds & close to hiking, skiing, shopping, & dining.

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.