Vacation rentals in Roxbury

4.98 out of 5 average rating, 162 reviews

The living room features a modern sofa and two armchairs, arranged around a coffee table. Large windows provide views of the surrounding woods, while natural light illuminates the wooden walls. A cozy atmosphere is created by the warm tones of the wood and plush seating.

Cabin in Roxbury

Secret Catskill Cabin: Spacious House w/Mtn Views

Just you and the sky. If you're looking for privacy in nature, this house is for you. Perched on a hilltop in Roxbury, surrounded by 10+ lush acres, our secluded log cabin comfortably hosts up to 10. Discover magnificent sunsets, whip-up family style meals in our open concept kitchen, get cozy by the fire, take in the night sky, and make memories to last a lifetime. Immerse yourself in nature, reconnect with loved ones, and enjoy 4 season activities at Belleayre, Plattekill, Windham, & Hunter!

A modern living area is highlighted by 20-foot vaulted ceilings and a wall of large picture windows framing lush mountain views. The space features a comfortable sectional sofa, a wooden coffee table, and a television on a media console. A cozy gas fireplace enhances the inviting atmosphere.

5 out of 5 average rating, 167 reviews

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

4.99 out of 5 average rating, 186 reviews

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

4.99 out of 5 average rating, 281 reviews

The exterior of Cupcake Cottage is framed by lush greenery, featuring a well-maintained lawn and vibrant flower beds. A spacious deck extends from the house, inviting relaxation and enjoying the surrounding natural beauty. Sunlight filters through the leaves, highlighting the cottage's warm wooden facade.

Barn in Roxbury

Cupcake Cottage! 1838 renovated barn, with views.

The 2025 vegetable garden is kicking in nicely! Tomatoes, beets, greens, peppers, beans and on and on. New: towels, hammock. 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 complete with old beams and rafters, and modern finishes of hemlock, red oak, and western red cedar throughout.

4.87 out of 5 average rating, 141 reviews

A bright open dining area is accented by a glass table surrounded by modern chairs. A chic wooden sideboard stands against the wall. Natural light floods through large windows, illuminating the warm wooden floors and the connected living space visible in the background.

Apartment in Roxbury

Sun-filled Victorian Apartment in the Catskills

Bright and peaceful in the quaint Catskills Mountain village of Roxbury, this two bedroom, one bath apartment with private entrance and porch in a historic Victorian residence is the perfect retreat to relax and explore the peaceful surroundings. Loft-like living room open to an eat-in kitchen. One Queen and one Double bedroom. Kitchenette with farm sink, convection oven, and cook plates. Full bath with clawfoot tub/shower. Play room/home office. Great closet space. Washer/dryer. TV. Wifi.

Bungalow in Margaretville

A garden brimming with vibrant orange flowers is set in front of a dark structure. A red building is visible in the background, surrounded by lush trees, adding to the green landscape. This serene outdoor space emphasizes a natural and welcoming environment.

4.97 out of 5 average rating, 314 reviews

The Porch Upstate Super clean

Halcottsville is a tiny hamlet In the heart of the Catskills .The porch is a compound with an old general store built in 1890 which is available for rent .We also have a restored barn , gardens and Apple orchard . The Bungalow is super private and still right on Main Street in Halcottsville. We will definitely will share our veggies and fruit with you . We have 3 sheep , 10 chickens and 5 barn cats .Halcottsville has its own post office ,voluntary fire department and a beautiful Lake.

4.9 out of 5 average rating, 138 reviews

The image captures a spacious lawn leading to a charming cottage, framed by lush trees on both sides. The deck of the cottage is visible, offering an inviting outdoor space. A small shed can be seen in the background, surrounded by greenery.

Cottage in Roxbury

Bellwood Cottage 8-14min to all Roxbury Wed Venues

Bellwood Cottage is perfect for couples, families, or groups of friends looking to get away from it all in an private, idyllic setting. Great for all seasons and close to skiing (20-40 min from Plattekill, Belleayre, Hunter and Windham), hiking, fishing, swimming holes, restaurants and quaint towns. Walk to downtown Roxbury and Kirkside Park via the scenic rail trail. Close to all wedding venues - 4 miles to Roxbury Barn, 7 miles to Stone Tavern Farm, 4 miles to The Inn at West Settlement.

4.94 out of 5 average rating, 175 reviews

The log cabin features a sloped metal roof and large windows, surrounded by trees. A spacious wooden deck with a railing offers outdoor seating options. The area is adorned with fallen leaves, enhancing the natural setting.

Cabin in Margaretville

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.

A serene spa area is illuminated by soft evening light, showcasing a saltwater hot tub surrounded by stone walls. Glass doors provide a view of the starry sky, while the surrounding snow adds a tranquil winter ambiance.

4.99 out of 5 average rating, 117 reviews

Catskills, secluded, a renovated 1840s Barn w/SPA

Welcome to PostBeamLove. An idyllic private secluded 4-season dream 10-acre getaway. Stay and indulge in complete comfort in a fully converted 1840s Dairy Barn with indoor saltwater hot tub & sauna with mountain views, overlooking the northwestern Catskills in the heart of Roxbury. The property features a spring-fed pond, gazebo, stream, & a neighboring farm. A 10-min drive to Plattekill Mtn, one of the best-kept secrets for avid skiers. Or go hiking, have a picnic, even golf.

The rustic cabin features a sloped green metal roof and a spacious wooden deck, surrounded by well-maintained gardens with colorful flowers. Lush trees provide a natural backdrop, enhancing the peaceful setting of the 12-acre property.

4.97 out of 5 average rating, 127 reviews

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.

The exterior of the home is showcased, featuring a prominent front porch with decorative railings. Lush green lawns surround the house, and trees line the background. The structure has a steep roof with dormer windows and a central door framed by elegant sidelights.

4.97 out of 5 average rating, 127 reviews

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.