Best Ashland Hotels

This historical Inn is just minutes from the Windham Ski area, as well as 2 professional golf courses, a vineyard, numerous state hiking trails and much more. This beautiful estate has 9+ bedrooms, 10.5 baths, a home office, large family gathering space, a large dining area, rec. room and living areas. Just 2.5 hours from the metropolitan area makes this an easy weekend commute. Come and see everything this beautiful house has to offer!This West Windham House has a brand new wrap around porch with roof. As well as a gas and charcoal grill for your family to enjoy. There is a new stainless steel refrigerator, six burner professional stove, Verizon Fios Internet, pool table, wood burning fireplace & washer & dryer in the home as well.Spacious covered front porch is complete with outdoor lighting, fan and plenty of seating, table and bar allow for comfortable outdoor gatherings, season to season. Providing an amazing view of the neighboring mountain tops.Multiple top-quality restaurants to choose from, movie theatre, mini golf, seasonal snow tubing, ski/snowboard your choice of three local mountains (Windham, Hunter and Belleyre) cyclist, golfers, hikers, bird watchers, nature enthusiast, explorers, mountain folk, musicians and music lovers will be at peace on Windhams' top Lodge, "A'Neils". About pets:Pets allowed.Pet fee applies..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No smoking inside the house..About minBookingAge:Minimum age to rent: 18.About events:Events allowed.Parties under age 25 need approval..

Dingley Dell Estate has a long history starting from the British Era. Dingley Dell Estate was originally founded in South Asia. This property is just minutes away from the Windham Ski Mountain and about 20 minutes from the Hunter Ski Mountain. The house has been tastefully decorated and finished to provide utmost comfort to our guests. This is a large house with huge manicured yards. Six bedrooms, four bathrooms, large kitchen, separate kitchenette and a beautiful deck overseeing the backyard. There are large gardens around the house ideal for ball games, badminton or simple walks. House offers large movie room with 100” QLED TV and enough seating for everyone. Guests can enjoy XL above ground pool from June till September as well as hot tub. About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No Shoes Inside the House.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Let this Magical Home take you away to your special place in the Catskills. Located nearby the town of Windham and less then 3 miles to Windham Ski Mountain this home is nearby all the activites that the Catskills has to offer. About pets:Pets allowed: limit 2 total.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

With a stay at this cottage in Ashland, you'll be within a 15-minute drive of Windham Mountain Resort and Windham Vineyards and Winery. This cottage is 13.6 mi (21.9 km) from Hunter Mountain and 1.7 mi (2.8 km) from Catskill State Park. Take in the views from a terrace and make use of amenities such as complimentary wireless internet access and gas grills. Free self parking is available onsite. Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven.

Newly Listed!! Beautiful mountain home located on a quite private road. This is a large 5 bedroom home only a few minutes from downtown Windham/Ski Resort and 20 minutes from Hunter Ski Resort. This property has massive lush green yards, amazing outdoor seating space, Weber BBQ Grill, superfast internet, and 5 minutes from downtown Windham. This property was recently renovated and fitted with all brand new appliances and furniture to provide utmost comfort for our guests.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Welcome to our creek house with expansive mountain views and open lush fields. After a long day of hiking, fishing, bike riding relax by the firepit overlooking the beautiful mountains. Enjoy a cup of joe while enjoying the sunrise and wind down with a glass of your favorite wine admiring the sunset.The house has 4 bedrooms, 2 full bathrooms, a well equipped kitchen and a deck overlooking the open field with a beautiful mountain in the backdrop.The house offers country charm with all modern amenities you’re accustomed to. With cable tv and wi-fi throughout, we’ve let no convenience go unaddressed. Enjoy meals without compromise in our fully functional kitchen, equipped with stainless-steel appliances and stocked with plates and utensils for cooking. Unwind by the firepit or on the deck overlooking the mountains or have fun with a game of foosball. Keep guests entertained with an array of board-games or spend quality time laughing, conversing, and making memories around the wood-burning fireplace.Whichever amenity you or your guests decide to enjoy, there are plenty to choose from and are guaranteed to create a truly memorable experienceAbout pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Come unwind, play and reconnect with the magic of nature in your own private mountain paradise, close to all the fun! 🌲⛰️❄️⛷️The Moon Cabin is the ultimate mountain home - rustic with a touch of style and luxury. Just minutes from Windham and Hunter Ski Mountains this private retreat is the perfect home base for adventure-filled days or quiet evenings spent playing games, telling stories, or simply enjoying each other’s company.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.

Welcome to Antler Ridge Estates! A beautiful, fully furnished, modern but rustic log cabin nestled in the Catskill Mountains of Windham, New York, only 6 minutes from Windham Mountain Ski Resort and 17 minutes to Hunter Mountain.True to its name, this is home to many white-tail deer and it is very common to find them grazing early morning and late in the afternoon in the field.Check us out on Instagram!@AntlerRidgeEstateYou’ll be greeted the moment you arrive by our stoic Buck Statues found at the entrance of the driveway. Continue onward to find Antler Ridge’s breathtaking Estate, privately situated on 6-plus acres with spectacular panoramic mountain views from just about every room and corner of the property. When you enter the home you will walk into the large family room that boasts a high log-beamed vaulted ceiling and large windows to take advantage of the spectacular mountain views. The room has a large sectional sofa, two armchairs, flat-screen TV, and a floor-to-ceiling stone wood-burning fireplace. As you move ahead you will enter the kitchen which is equipped with stainless steel appliances, granite countertops, and a large center island that seats 6. You will also find all plates, glasses, and utensils waiting to be set at the dining table which also seats 6. Continue through to the master bedroom (Bedroom #1) equipped with a flat-screen TV and ensuite which has double sinks, jetted tub, and a stall shower. You can also access the deck from the master bedroom! Walk upstairs to a large but cozy sitting area where you can play chess or just relax and read a book, or even watch TV from the family room below. There are 3 bedrooms individually decorated in a woodland/cabin theme. Bedroom #2 has 1 queen bed, Bedroom #3 has 2 full beds, and bedroom #4 has two 2 full beds. A full bathroom complete with a tub/shower combo is centrally located in the main hall. This home sleeps 14 comfortably. Come back down the stairs and head down to the lower level. Yes, we saved the best for last!… a fully furnished walkout game room that has all the ingredients for a good time: a flat-screen TV, foosball, air hockey, ping pong, pool table, poker table, arcade games, a dartboard, bar, and an electric fireplace. This space also leads out to the lower patio with a hot tub, and seasonal seating. And for the kids or gamers who don’t want to leave our fantastic Game Room, you’ll also find bedroom #5 with two twin beds! Lastly, step outside to relax on the deck, soak in the hot tub, grill on the patio, or toast marshmallows around the fire pit! Oh and don’t forget our putting green for the adults to practice and a swing set for the kiddos!! So, come and relax, unwind and enjoy the luxury, quiet, and calmness that the Catskills has to offer. Or, if relaxing isn’t your thing and adventure is, we are located just 4 miles from Windham Mountain which has many trails to ski and snowboard, and snow tubing. There is a sky ride, bike park, golfing, fishing, kayaking, canoeing, and many walking and hiking trails. Although shops and restaurants are only a 10-minute drive away, the area feels peaceful, private, and secluded.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

The Cave Mountain Motel is an ideal spot for travelers wanting to discover the city. The Cave Mountain Motel is an ideal choice for travelers who want to take in the sights and sounds of Ashland. There is no shortage of things to see in the area, with the Mountain Breeze Yoga & Sound Therapy, Windham Mountain Club and Windham Mountain Bike Park all nearby. When guests have some time on their hands they can make use of the onsite facilities. Guests of this Ashland hotel can make use of the parking facilities.

Welcome to this charming cottage minutes from Windham and Hunter Mountains. This terrific one-bedroom retreat features a cool living room with a sofa bed, perfect for extra guests. A full kitchen and a banquette is included. Guests can enjoy amenities like a hair dryer, heating, AC, WiFi, and a washing machine/dryer. Experience what Ashland has to offer with a stay at our cozy cottage and a hot tub.About pets:Pets allowed: limit 1 total.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.