Holiday rentals in Roxbury

Windswept Cottage close to skiing & wedding venues

Windswept Cottage is a country cape, 3 bedrooms and 2 baths house on a quiet street in Roxbury, NY. Enjoy the outdoors, yard, sundrenched deck, frog & koi pond. Hike out the back door to John Burroughs' childhood home and picnic rock. It is a two family home with the owner/caretaker on the premises. Vicki & Don are the owners of 'Maid My Day', an award-winning housecleaning service and presently follow AirBnB's "Enhanced Cleaning Guidelines". You have off-street parking 40ft from the house.

Cupcake Cottage! 1838 renovated barn, with views.

Spring has arrived! The flowers are popping up. Two night rentals are available from January-May. New 2026: Kitchen Aid Stand Mixer. Cupcake Cottage has had a total renovation: the same light, charm, and views remain but inside there is a new kitchen, flooring, and heating system. And outside, a new deck and porch configuration, windows, siding, roof and dormers. The house is an 1838 barn with old beams and rafters, and modern finishes of hemlock, red oak, and western red cedar throughout.

Mountainscape: Peaceful- Skiing & Hiking

Our property is nestled in the Catskills mountains, offering mountain views and serene landscapes. You'll be staying in a cabin with 2 beds, Queen & Full, fold out couch, a kitchen, Wi-Fi, fire pit, & charcoal grill. Games to play both inside & outside provided. 4 ski resorts 16-32 min away such as Plattekill, Belleayre, Hunter, Windham Mountains. Nearby: Scenic Railcar rides, Cooperstown Baseball Hall of Fame, Howe Caverns, hiking, kayaking, biking & waterfalls. Restaurants in driving distance.

Private 3BR escape w/ sweeping Mt Views & Firepit!

Click: "Show more" to read description before booking. No pets Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse w/ sweeping mountain views! Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

Spacecraft Sanctuary x Stargate Self-Care Retreat

Nestled into a private forested locus in the charming hamlet of Halcottsville, NY is SPACECRAFTX1 SANCTUARY, a transformed single wide trailer with walls of glass sliders that showcase the ultimate designer, Mother Nature with her majestic mountain vistas, perennial x calming Japanese rock gardens. SPACECRAFTX1 STARGATE (separate structure) is a wellness studio for yoga, pilates, barre x meditation with an infrared sauna with chromotherapy for a “Design Your Own” self-care retreat experience.

Peaceful Designer Farmhouse~Hot Tub~Sunset Porch

Revel in the design of this recently renovated 3BR 1.5Bath oasis surrounded by the Catskills Mountains. It's a perfect base for your ski weekend or wedding party, nestled on the historic Burroughs Memorial Road, where the famous naturalist entertained Henry Ford and Teddy Roosevelt. ✔ Hot Tub & Fire Pit ✔ 3 Comfy BRs ✔ 2 Living Areas ✔ Chef's Kitchen ✔ Wraparound Porch (BBQ Grill, Seating) ✔ HD Projector with a Wide-Screen ✔ Guitars & Drum Set ✔ High-Speed WiFi ✔ Free Parking See more below!

Andes Valley View

This home is a beautiful mix of cozy and modern. You’ll love cooking in the kitchen and taking in the view from the second story deck. The property is stunning, with wide meadows and dense woods. There are 140 acres to explore and utilize for events like weddings or a retreats. There is a half acre pond with a pond house at the top of the property and a trout stream running along the bottom. It’s everything you could hope for in a Catskills getaway, all nestled overlooking the town of Andes.

Catskills log cabin in the sky with mountain views

Welcome to Cabin in the Sky! At 1,671 ft elevation, Cabin in the Sky is a newly renovated log cabin nestled in the mountainside with tranquil views. The home offers the perfect combination of seclusion and convenience. In the mornings/evenings, enjoy a cup of coffee or glass of wine from the private deck which overlooks pure nature (not a car, street or building in sight). During the day, take advantage of the local hiking, skiing, farmer's markets, restaurants and shopping.

Mountain and tree view cabin on 12 private acres

A great escape awaits you on 12 acres of private land. If you prefer a relaxing vacation or if you want to get involved in local activities (hiking, biking, swimming, skiing, snowshoeing, sledding), this is your place. Enjoy 360 degree views of the Catskill Mountains from almost anywhere on the property. Sip your morning coffee while watching the sunrise on the large deck. Play in the large private yard. Clear evenings are the best for sunsets, a fire pit and star gazing.

Luxury Designer Dome Private Oasis in Catskills

* MOST WISHLISTED AIRBNB IN NY STATE! * Welcome to the Shell House, an idyllic and uniquely designed four season retreat nestled on 5 private acres. Enjoy breathtaking mountain views from every room, cozy bedrooms for peaceful nights, and expansive outdoor spaces perfect for relaxation. Just minutes from nearby towns and the best of the Catskills, this light-filled sanctuary invites you to unwind, reconnect with nature, and create lasting memories with loved ones.

Modern Getaway with Mountain Views

This spacious, modern home is located on 9+ acres of open fields and woods. Have your morning coffee on the front porch, gather with the family for meals in the open concept kitchen, or spend a relaxing evening outdoors under the stars. Enjoy views of the nearby mountains from the hot tub on the deck. Our secluded home off a paved road is the perfect place for doing everything or nothing at all. Close to Belleayre, Plattekill, Hunter, and Windham.

Modern & Chic Log Home-Spectacular Mountain Views!

Welcome to Fox Ridge Chalet! Minimum age to book 21. A newly renovated, stylish log cabin nestled on 7 private acres above the village of Margaretville, in the heart of Catskills Park. Though the home is secluded, offering spectacular mountain views and total privacy, it’s just a three-minute drive to Margaretville’s restaurants, shops and galleries and under ten minutes to Belleayre Ski Resort as well many other local attractions.