Vacation rentals in Roxbury

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Top-rated vacation rentals in Roxbury

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Cabin in Margaretville

4.98 out of 5 average rating, 125 reviews

Retreat in the sky - Hot Tub with Panoramic Views

Welcome to the Big Rock Cabin. Perched on a mountain in Catskills with panoramic views and modern amenities. Local attractions include Belleayre, Plattekill , Wyndham & Hunter Ski resorts, hiking, swimming holes, golf, kayaking, farm markets, antique stores, restaurants, wedding venues and more. Spend a day outdoors. relax in the 6 person Hot Tub, light a fire outside or curl up by the fireplace. Chef's kitchen, Air conditioned rooms. A fenced front yard is ideal for those with kids or pets.

Top guest favorite

A cozy living area features large floor-to-ceiling windows allowing natural light to illuminate the space. A combination of comfortable seating includes stylish armchairs and a sectional sofa, arranged around a wooden coffee table atop a colorful rug. Natural wood paneling complements the serene forest view.

Cabin in Roxbury

4.98 out of 5 average rating, 159 reviews

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!

Top guest favorite

An exterior view showcases a comfortable wooden chair on the deck, accompanied by a glowing lantern and a glass of wine. The scene features a gentle dusk light, with trees and distant hills creating a serene backdrop, and warm lights lining the outdoor space.

Home in Roxbury

5 out of 5 average rating, 161 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

Superhost

A vibrant farmer's market is depicted, bustling with visitors and surrounded by lush greenery. Stalls with colorful canopies are set up, showcasing various local goods. A large red barn stands prominently in the background, enhancing the rural charm of the scene.

Apartment in Roxbury

4.86 out of 5 average rating, 139 reviews

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.

Top guest favorite

Bungalow in Margaretville

4.97 out of 5 average rating, 303 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.

Top guest favorite

A hot tub filled with clear water is positioned on a wooden deck, surrounded by a snow-dusted railing. Nearby, picnic tables provide seating options, and scattered greenery adds a natural touch to the serene winter scene.

Cabin in Roxbury

4.99 out of 5 average rating, 145 reviews

Vacation destination! Hottub, Games, View, Firepit

Cozy Catskills Retreat – Perfect for All! Nestled in the Catskills, our charming Airbnb is ideal for family, friends, or a quiet getaway. Enjoy a Hot Tub, peace and quiet, ski at Plattekill, Belleayre, Hunter or Windham, or attend nearby weddings. Relax in the hot tub, cook in the fully equipped kitchen, and unwind on the private deck. With spacious living areas, it’s perfect for celebrations or quiet escapes. Discover hiking, local charm, and starry nights—your Catskills adventure awaits!

Guest favorite

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

4.94 out of 5 average rating, 168 reviews

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.

Top guest favorite

A charming exterior view of a blue house with large windows and a welcoming deck. Two red chairs are situated on the deck, surrounded by well-maintained grass and a stone border. Lush trees and a clear blue sky create a serene outdoor environment.

Home in Roxbury

4.99 out of 5 average rating, 113 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.

Top guest favorite

A spacious deck features two comfortable chairs facing a breathtaking view of rolling hills blanketed in mist. Soft morning light illuminates the landscape, highlighting the vibrant autumn colors in the trees and creating a serene atmosphere.

Home in Roxbury

4.97 out of 5 average rating, 126 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.

Top guest favorite

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

4.99 out of 5 average rating, 278 reviews

Cupcake Cottage! 1838 renovated barn, with views.

Early spring rates are in effect, with 2 night minimum rentals from Feb-May, and 3 the rest of the year. 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.

Top guest favorite

A spacious front porch features several green rocking chairs arranged along a wooden railing. Hanging planters filled with flowers add color, and the surrounding landscape includes well-maintained lawns and trees, creating a welcoming atmosphere for relaxation.

Home in Roxbury

4.98 out of 5 average rating, 121 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.

Top guest favorite

Guest suite in Roxbury

4.98 out of 5 average rating, 120 reviews

PLaYful New! 2 bed apart In Beautiful Catskills

New 2 bedroom apartment in Roxbury New York. Fun and comfortable , on a 4 acres property with beautiful views down our lawn to a frog filled pond. You are in the building with a yoga studio.We hold classes on Saturday, Sunday and Monday at 10 am. You have a private entrance, a private patio with great outdoor space for both work and play with a lovely outdoor chimera for cool nights under a star studded sky. Gas grill - ready for a great escape.