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Vacation rentals in Town of Ashland

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Top-rated vacation rentals in Town of Ashland

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Top guest favorite
The living area features a cozy arrangement with a gray sectional sofa and an orange armchair, inviting relaxation. A modern television is mounted above a black fireplace, which is framed by natural wood accents. Large windows allow natural light to fill the space, showcasing rustic wall textures.
Cabin in Town of Ashland

Luxury Cabin Retreat - 7 Mins to Windham

The perfect blend of rustic charm, luxury and style just minutes from Windham and Hunter Mountains, this private retreat is the upstate escape you’ve been dreaming of. When you walk in the cabin you'll instantly feel the warm embrace of mountain living. Cozy up by the wood burning fire, enjoy a cup of tea in the sunlit breakfast nook or gather together around the modern kitchen island to connect and unplug. Every space throughout has been thoughtfully designed for tranquility and reconnection.

5.0 out of 5 average rating, 32 reviews
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

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

4.99 out of 5 average rating, 155 reviews
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

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 :)

5.0 out of 5 average rating, 420 reviews
Guest favorite
Cabin in Windham

Cozy Family-Friendly A-Frame - Windham with AC

Escape to this peaceful A -Frame mountain retreat in the Catskills. Windham is know as the “Gem of the Catskills” and was recently named as a big charm town and perfect for a weekend getaway in New York by World Atlas. Only 5 minutes from Windham Mountain with skiing and snowboarding, hiking, golfing, restaurants and shops. Relax and enjoy with the whole family and friends around the fireplace, game room, or large deck. We believe without a doubt you will love this home as much as we do!

4.96 out of 5 average rating, 24 reviews
Guest favorite
Home in Windham

Windham Villa | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate blending refined luxury, comfort, and privacy. Nestled within the exclusive Dingley Dell Estate, just six minutes from Windham town and 25 minutes from Hunter Ski Resort. Enjoy beautifully landscaped grounds, inviting outdoor spaces, complete privacy, and breathtaking mountain views. Fully renovated for exceptional comfort, the home features a private pool, movie room, premium sound system, and everything needed for an unforgettable luxury mountain escape.

4.95 out of 5 average rating, 109 reviews
Top guest favorite
A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.
Home in Lexington

Valley View Chalet: AC, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

4.99 out of 5 average rating, 171 reviews
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

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.

4.95 out of 5 average rating, 515 reviews
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

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!

4.96 out of 5 average rating, 233 reviews
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

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.

4.98 out of 5 average rating, 198 reviews
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

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!

4.94 out of 5 average rating, 120 reviews
Top guest favorite
Home in Prattsville

Catskills Retreat - Game Room, Hot Tub, EV charger

Welcome to our Mountain Chalet. Bring the whole family to this spacious retreat with plenty of room for fun and relaxation.This specious house, nestled on 2.5 acres, features 4 bedrooms, 3 full bathrooms, Hot Spring hot tub, a game room, a cozy gas fireplace, smart TVs, an EV charger and more. It has beautiful views. Located in the heart of the Catskills, 15 min from Windham Mountain, 20-25 min from Hunter and 40 min from Belleayre. Your perfect mountain getaway awaits!

4.97 out of 5 average rating, 107 reviews
Guest favorite
Cabin in Windham

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.

4.95 out of 5 average rating, 226 reviews

Popular amenities for Town of Ashland vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Town of Ashland

Top guest favorite
A spacious living area features a plush sectional couch adorned with decorative pillows, positioned near large windows that provide views of the surrounding trees. A coffee table with a decorative centerpiece sits in front. The open-concept layout includes a glimpse of the kitchen and dining area in the background.
Home in Prattsville

Modern Mountain Home - Near Windham & Hunter ski!

5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Windham

Creekside Lodge | 7 Min to Skiing | Sleeps 12

4.93 out of 5 average rating, 72 reviews
Top guest favorite
Home in Prattsville

Hot Tub • Sauna • Mtn View • Firepit • Home Office

5.0 out of 5 average rating, 33 reviews
Top guest favorite
Home in Windham

Modern Forest Retreat with Hot Tub and Sauna

5.0 out of 5 average rating, 18 reviews
Top guest favorite
Home in Prattsville

10 min to Windham! 20 min to Hunter! EV charger!

5.0 out of 5 average rating, 44 reviews
Guest favorite
A serene landscape showcases a tranquil pond reflecting the vibrant fall foliage and the Batavia House in the background. Trees with golden leaves surround the area, enhancing the peaceful rural atmosphere. The lush green grass leads gently to the water's edge.
Home in Town of Ashland

Arcade|Music|BBQ|Fire Pit|Acres|Batavia House!

4.9 out of 5 average rating, 67 reviews
Top guest favorite
A custom log home features a prominent stone chimney and a spacious front porch with wooden railings. Surrounding greenery and mature trees complement the natural setting. A well-maintained lawn extends to the stone pathway leading to the entry, showcasing a serene outdoor ambiance.
Home in Prattsville

Gem w Hot tub/Pond/ 9 min to Ski

5.0 out of 5 average rating, 10 reviews
Top guest favorite
Cabin in Jewett

Catskills Mountain Retreat: Luxury Meets Serenity

5.0 out of 5 average rating, 19 reviews

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.

Destinations to explore