Find the Best Ashland Hotels

With a stay at Cave Mountain Motel in Windham, you'll be in the mountains, within a 5-minute drive of Windham Mountain Resort and Ashland Park. This motel is 12.7 mi (20.5 km) from Hunter Mountain and 2.8 mi (4.6 km) from Ashland Town Hall. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and a picnic area. A complimentary buffet breakfast is included. Free self parking is available onsite. Make yourself at home in one of the 8 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have showers and complimentary toiletries.

When you stay at Silas House in Lexington, you'll be near ski lifts, within a 5-minute drive of Prattsville Town Hall and Zadock Pratt Museum. This inn is 14.9 mi (24 km) from Hunter Mountain and 17.4 mi (28.1 km) from Catskill Mountains. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and ski storage. Additional features at this inn include gift shops/newsstands, wedding services, and a communal living room. A complimentary continental breakfast is served on weekends from 9:00 AM to 11:00 AM. Featured amenities include a computer station, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 4 guestrooms featuring refrigerators and microwaves. Prepare your meals in the shared/communal kitchen. Complimentary wireless internet access is available to keep you connected. Bathrooms have separate bathtubs and showers and hair dryers.

With a stay at Moore's Motel in Prattsville, you'll be within a 10-minute walk of Pratt Museum and Zadock Pratt Museum. This motel is 11.2 mi (18.1 km) from Windham Mountain Resort and 0.4 mi (0.6 km) from Prattsville Town Hall. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this motel include complimentary wireless internet access, a picnic area, and barbecue grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 16 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access is available to keep you connected. Bathrooms with showers are provided.

With a stay at Black Bear Lodge in Prattsville, you'll be within a 10-minute drive of Prattsville Town Hall and Zadock Pratt Museum. This motel is 11.3 mi (18.2 km) from Hunter Mountain and 13.8 mi (22.3 km) from Catskill Mountains. Make use of convenient amenities, which include complimentary wireless internet access and a television in a common area. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 8 guestrooms. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Bathrooms with showers are provided.

With a stay at Beds on Clouds in Windham, you'll be near ski lifts, within a 5-minute drive of Windham Mountain Resort and Windham Country Club. This guesthouse is 10.6 mi (17.1 km) from Hunter Mountain and 4.9 mi (7.9 km) from Ashland Park. Pamper yourself with onsite massages or enjoy recreation amenities such as bicycles to rent. Additional features at this guesthouse include complimentary wireless internet access, tour/ticket assistance, and a picnic area. Getting to nearby attractions is a breeze with the area shuttle (surcharge). Featured amenities include express check-in, express check-out, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 5 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have showers and complimentary toiletries. Conveniences include electric kettles and ceiling fans, and housekeeping is provided daily.

With a stay at Winwood Inn & Condominiums in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Mountain Resort and Windham Country Club. This family-friendly hotel is 10.2 mi (16.4 km) from Hunter Mountain and 15.6 mi (25.2 km) from Kaaterskill Falls. Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. Skiers will be in heaven, but there are recreational options available for non-skiers as well, which include a seasonal outdoor pool. This hotel also features complimentary wireless internet access, concierge services, and an arcade/game room. The complimentary ski shuttle makes getting to the slopes a breeze. At Winwood Inn & Condominiums, enjoy a satisfying meal at the restaurant. Featured amenities include express check-out, a 24-hour front desk, and luggage storage. Free self parking is available onsite. Stay in one of 48 guestrooms featuring flat-screen televisions. Complimentary wireless internet access is available to keep you connected. Conveniences include blackout drapes/curtains, and housekeeping is provided daily.

There’s a familiar feeling as you cross the bridge over the Batavia Kill and arrive at Wylder Windham. This is where you belong. It’s a place where the sound of laughter mixes with the rustling of leaves, where the flow of the river sets the pace for your day, and the flicker of fireflies illuminates your night. With 20 acres of pastoral land and the Batativa Kill running through it, our family-friendly, all-season resort is filled with endless opportunities for recreation and relaxation. Whether tubing on the river, gathering with friends around the firepit or going skiing at nearby Windham Mountain, this is a place that captures the nostalgic spirit of the Catskills and celebrates the timeless pleasures that this land has to offer.

With a stay at Eastwind Windham in Windham, you'll be within a 5-minute drive of Windham Mountain Resort and Windham Country Club. This hotel is 9.7 mi (15.6 km) from Hunter Mountain and 17.4 mi (28 km) from Kaaterskill Falls. Wrap up your day with a drink at the bar/lounge. Continental breakfasts are available daily from 8:00 AM to 10:30 AM for a fee. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 26 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms feature showers with rainfall showerheads and hair dryers. Conveniences include desks and desk chairs, and housekeeping is provided on request.

With a stay at Albergo Allegria Hotel & Breakfast Restaurant in Windham, you'll be next to a golf course, just a 5-minute walk from Windham Country Club and a 4-minute drive from Windham Mountain Resort. This golf bed & breakfast is 7.1 mi (11.4 km) from Windham Vineyards and Winery and 9.5 mi (15.2 km) from Hunter Mountain. Take advantage of recreation opportunities such as bicycles to rent or take in the view from a terrace and a garden. This Victorian bed & breakfast also features complimentary wireless internet access, concierge services, and ski storage. At Albergo Allegria Hotel & Breakfast Restaurant, enjoy a satisfying meal at the restaurant. Cooked-to-order breakfasts are available daily for a fee. Featured amenities include a business center, express check-in, and express check-out. Free self parking is available onsite. Make yourself at home in one of the 21 individually decorated guestrooms, featuring DVD players and flat-screen televisions. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers.

When you stay at Hotel Vienna in Windham, you'll be next to a golf course, within a 5-minute drive of Windham Country Club and Windham Mountain Resort. This golf hotel is 7.4 mi (12 km) from Windham Vineyards and Winery and 9.2 mi (14.8 km) from Hunter Mountain. Take advantage of recreation opportunities such as an indoor pool or take in the view from a terrace and a garden. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and ski storage. A complimentary continental breakfast is served daily from 7:30 AM to 10:00 AM. Featured amenities include a business center and express check-out. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers.