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Located in Great Barrington, The Old Inn On The Green is a 5-minute drive from Dry Hill and 7 minutes from Questing. This inn is 3.8 mi (6.1 km) from Umpachene Falls Park and 4.8 mi (7.8 km) from Les Trois Emme Winery. Take advantage of recreation opportunities such as a seasonal outdoor pool or take in the view from a terrace and a garden. Stop by The Old Inn Fine Dining for lunch, dinner, or brunch, where this restaurant specializes in American cuisine, or grab snacks at the coffee shop/cafe. Mingle with other guests at the complimentary reception, held on select days. Quench your thirst with your favorite drink at the bar/lounge. A complimentary continental breakfast is served daily. Free self parking is available onsite. Make yourself at home in one of the 11 individually decorated guestrooms. Rooms have private balconies or patios. 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 Gedney Farm in Great Barrington, you'll be near ski lifts and within a 5-minute drive of Dry Hill. This hotel is 2.8 mi (4.5 km) from Questing and 3.6 mi (5.8 km) from New Marlborough Town Hall. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional features at this hotel include wedding services, a communal living room, and a picnic area. Satisfy your appetite at Restaurant, a restaurant which features a bar/lounge and a garden view. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include a safe deposit box at the front desk and refrigerator in a common area. Planning an event in Great Barrington? This hotel has 1950 square feet (181 square meters) of space consisting of conference space and 4 meeting rooms. Free self parking is available onsite. Make yourself at home in one of the 16 individually furnished guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms have complimentary toiletries and hair dryers. Conveniences include blackout drapes/curtains, housekeeping is provided daily, and microwaves can be requested.

With a stay at Wilder House Berkshires in Sheffield, you'll be within a 5-minute drive of Lime Kiln Farm Wildlife Sanctuary and Thom Reed UFO Monument Park. This bed & breakfast is 2.2 mi (3.5 km) from Drury Preserve and 2.2 mi (3.6 km) from Magnolia Bluffs Casino. Take in the views from a garden and make use of amenities such as a picnic area. A complimentary cooked-to-order breakfast is served on weekdays from 8:00 AM to 10:00 AM and on weekends from 8:00 AM to 10:00 AM. 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 digital programming is available for your entertainment.

Located in East Canaan, Locust Tree Bed and Breakfast LLC is within a 5-minute drive of Lawrence Field and Beckley Furnace Industrial Park. This bed & breakfast is 1.3 mi (2.1 km) from Edith Scoville Memorial Sanctuary and 1.4 mi (2.2 km) from Connecticut Railroad Historical Museum. A complimentary full breakfast is served daily from 8:00 AM to 9:30 AM. Free self parking is available onsite. Stay in one of 7 guestrooms featuring flat-screen televisions. Cable television is provided for your entertainment.

When you stay at East Rock Inn in Great Barrington, you'll be near ski lifts, within a 5-minute drive of Ski Butternut and Housatonic River Walk. This motel is 4.1 mi (6.6 km) from W.E.B. Du Bois Boyhood Homesite and 7.6 mi (12.2 km) from Naumkeag Museum. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and ski storage. Featured amenities include express check-in and express check-out. Free self parking is available onsite. Stay in one of 18 guestrooms featuring Smart televisions. Your pillowtop bed comes with premium bedding. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms have designer toiletries and hair dryers.

With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River Walk. This motel is 1.6 mi (2.6 km) from Mahaiwe Performing Arts Center and 1.9 mi (3.1 km) from Beartown State Forest. Make use of convenient amenities such as 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 17 air-conditioned rooms featuring refrigerators and microwaves. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and irons/ironing boards, as well as phones with free local calls.