Vacation rentals in Town of Ashland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Town of Ashland

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

1 of 1 pages1 / 1
Top guest favorite
Cabin in Roxbury
4.97 out of 5 average rating, 129 reviews

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.

Guest favorite
A spacious outdoor deck is showcased, featuring two white lounge chairs positioned opposite a small glass table. Lush green hills are visible in the background under a partly cloudy sky, highlighting the serene natural surroundings of the retreat.
Home in Halcottsville
4.93 out of 5 average rating, 376 reviews

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.

Guest favorite
The living room features a modern design with tall windows allowing natural light to fill the space. A black fireplace serves as a focal point, surrounded by comfortable seating. A cozy area rug enhances the atmosphere, while decor items add subtle artistic touches.
Cabin in Windham
4.97 out of 5 average rating, 135 reviews

Catskills Designer Retreat near Hiking + Swimming

★ One of Airbnb’s Most-Loved Design Homes in the Catskills ★ Relax & recharge at Casa Magda—a design-forward retreat on 9 acres in Windham, just 2.5 hours from NYC. Perfect for design lovers and nature seekers, this renovated 1980s gem blends modern style w/peaceful seclusion. Unwind in the hot tub, cozy up by the fireplace w/a record, or gather around the firepit beneath star-filled skies. Explore nearby restaurants and trails, ski Windham Mountain 7 mins away or head to Hunter in 15 mins.

Top guest favorite
The A-frame chalet is framed by lush greenery, featuring a dark exterior with large windows. A bright blue door welcomes guests, and a private balcony extends from the upper level. Natural light reflects off the exterior, highlighting the home's inviting design.
Home in Prattsville
4.98 out of 5 average rating, 133 reviews

Scandi A-Frame w/Hot Tub & Sauna

Escape to Wilderkaat {WILL-der-cat} ⮕ NEW GUT RENO 3-bed 2-bath Scandinavian modern A-frame chalet ⮕ 2 private wooded acres ~10 miles to Hunter & Windham ⮕ 8-person hot tub, cold plunge tub, 6-person barrel sauna ⮕ Backyard firepit w/Adirondack chairs & string lights ⮕ Outdoor games: bocce cornhole horseshoes disc golf ⮕ Fully stocked open kitchen, Weber grill, in & outdoor dining for 8 ⮕ Smart TVs & Sonos throughout, high-speed fiber WiFi ⮕ A Catskills perfect blend of relaxation & adventure

Top guest favorite
The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.
Home in Windham
5 out of 5 average rating, 405 reviews

Private cabin in the Catskills

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Top guest favorite
An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.
Cabin in Windham
4.95 out of 5 average rating, 496 reviews

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

Guest favorite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter
4.96 out of 5 average rating, 212 reviews

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Guest favorite
The chalet stands amidst vibrant autumn foliage, showcasing a green exterior and a spacious deck. The well-maintained yard features a lush green lawn, with a variety of trees surrounding the property that enhance the natural setting.
Guesthouse in Windham
4.98 out of 5 average rating, 195 reviews

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Guest favorite
An inviting great room features a wood-burning fireplace surrounded by natural stone. Expansive windows frame views of the outdoors, while warm wood beams and flooring enhance the cozy atmosphere. A mix of seating options, including a leather sofa and wooden chairs, create a welcoming gathering space.
Chalet in Windham
4.94 out of 5 average rating, 116 reviews

Secluded Fernwood Chalet, Hot Tub, & Sauna House

Come immerse yourself in the beauty of the Catskills and enjoy the Fernwood chalet featuring mountain views and set upon 32 acres with private hiking trails, a hot tub, and a sauna house! Enjoy skiing in the winter (9 min. To Windham mtn., 18 to Hunter)hiking when it's warmer, fishing, swimming holes, lakes, you name it! Several wonderful dining options in the town of Windham, farmers markets & festivals, and other excursions a short drive away, or simply zen out at Fernwood!

Top guest favorite
Cabin in Windham
4.95 out of 5 average rating, 204 reviews

Cozy Creekside Cabin | 5 Mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

Top guest favorite
Cottage in Halcott Center
4.98 out of 5 average rating, 365 reviews

Cozy Cottage with Stunning Mountain Views

Welcome to Halcott Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

Top guest favorite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 160 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Popular amenities for Town of Ashland vacation rentals

Frequently Asked Questions

  • What are the best places to stay in Ashland?

    Staying in cozy cabins, farmhouses, or countryside rentals in and around Ashland provides a peaceful setting. Rentals surrounded by woodland or mountain views are frequently suggested for those seeking a tranquil retreat.

  • What are the best things to do in Ashland with kids?

    Families often explore nature trails, visit small farms, or try fishing in local creeks around Ashland. Picnicking in open meadows and participating in seasonal farm activities, like berry picking, are also popular among children.

  • What are some of the best things to do in Ashland?

    Explore quiet country roads, hike in nearby forests, and relax by small lakes around Ashland. The area has opportunities for birdwatching, seasonal foliage walks, and visits to local farm stands or craft studios.

  • How is the weather in Ashland?

    Ashland experiences cold winters with temperatures ranging from 16–38°F (-9–3°C), and warm summers around 62–84°F (17–29°C), along with regular rainfall throughout the year. Snow is common in winter, while autumn draws visitors for colorful foliage.

  • When is the best time to visit Ashland?

    Late spring through early autumn is often recommended for mild weather and vibrant outdoor scenery. Fall brings especially colorful foliage, while summer is popular for outdoor recreation and local festivals.

  • What are the best places to visit in Ashland?

    Explore quiet forests, local farm stands, and small artisan shops found throughout Ashland. Scenic viewpoints, picnic areas, and community markets are also frequently suggested for visitors.

  • What are some hiking trails in Ashland?

    Ashland has wooded paths and gentle trails through forests and meadows, suitable for both new and experienced hikers. Trails often feature birdwatching opportunities, streams, and seasonal wildflowers.

  • What are some family activities we can do in Ashland?

    Families in Ashland often enjoy outdoor picnics, gentle hiking trails, and visits to nearby animal farms. Nature scavenger hunts and exploring local markets are engaging for a range of ages.

  • What are some of the best day trip ideas from Ashland?

    Explore nearby state parks, tour cideries or wineries, and visit mountain towns around Ashland known for distinct crafts and local foods. Scenic drives through the Catskills are often highlighted, especially during peak foliage or when local markets are in season.

  • Are there any pet friendly accommodations available in Ashland?

    Many country rentals and cabins in Ashland welcome pets, making it possible to bring dogs on your getaway. Outdoor spaces and proximity to trails make exploring with a pet straightforward for visitors.

  • What are some local tips for visiting Ashland?

    Bringing layers is suggested, as weather can change quickly, especially in spring and fall. Locals often recommend exploring the quieter backroads and chatting with area artisans or market vendors for unique finds.

  • What is Ashland known for?

    Ashland is known for its peaceful rural atmosphere, scenic mountain views, and outdoor activities like hiking and fishing. Its locally rooted art and agricultural traditions draw those interested in slower-paced, nature-focused experiences.

  • What are the best hidden gems to explore in Ashland?

    Ashland has tranquil forest paths, small art studios, and off-the-beaten-path streams that attract those who enjoy quieter experiences. Local antique shops and tucked-away picnic spots are also worth exploring for a slower pace.

  • What are the best foods to try in Ashland?

    Ashland has hearty, locally sourced fare such as farm-fresh produce, homemade pies, and New York-style pizza. You may also find locally roasted coffee and classic diner breakfasts often suggested by visitors.

  • What should I bring for a trip to Ashland?

    Bring versatile clothing layers for changing weather, comfortable hiking shoes, and a rain jacket. If you plan to spend time outdoors, sun protection, insect repellent, and a reusable water bottle are also useful.

  • What is the nightlife in Ashland like?

    Nightlife in Ashland is laid-back, with casual taverns and local gathering spots emphasizing conversation, regional brews, or acoustic music. The area is known more for quiet evenings and stargazing than late-night venues.

  • What are the most popular events or festivals in Ashland?

    Community fairs, craft festivals, and farmers markets are often highlighted throughout the year in Ashland and surrounding towns. Seasonal celebrations, including fall harvest festivals and summer outdoor concerts, are also frequently suggested.

  • Are there family friendly vacation rentals in Ashland?

    Ashland has inviting vacation rentals suitable for families, including homes with outdoor space and kitchens for easy meal preparation. Many rentals in the area cater to groups looking for a comfort-focused, family atmosphere.