Holiday rentals in Lanesborough

Lakefront Home on Ponstoosuc Lake, The Berkshires

Stunning lakefront property on 1-acre on Pontsoosuc Lake in western MA, in the heart of the Berkshires. This beautiful home features 3 bdrms & 2.5 baths. A large primary suite (king bed) sits on one side of the home, w/ two guest bdrms (king bed, queen bed) on the other end of the house. Kitchen, dining, and living room areas are spacious and open, with high ceilings & skylights. Cozy closed-in lakeside backporch opens to a small back deck. Large front side porch is set back from main road.

Marie's Place, Unit 1

This bright sunny apartment is only minutes from downtown restaurants and theaters, and local lakes. This is a beautiful 3 bedroom apartment, offers 2 queen beds and in the smaller bedroom a double. It has a large eat in kitchen and a large living room where you can play games or watch a movie on the 43 inch Roku TV. For winter stays we are only a short distance from all Berkshire County ski areas. The AC units are installed from June-September. There is off street parking for at least 2 cars.

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Beautiful Lake-view Getaway!

Enjoy a weekend away in the heart of The Berkshires! Take in the stunning lake views and beautiful sunsets year-round. Whether you are looking for a lake getaway or Berkshires retreat in the summer, or a place to cozy up after a long day of skiing in the winter, my home will offer all the comforts you need to enjoy your time in The Berkshires. Enjoy the lake views from the hot tub (additional fee), sit around the fire pit and watch the sun set, or enjoy a home cooked meal on the patio!

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. The house is spacious and welcoming with a sunny deck and welcoming porch. Dog friendly with a fully enclosed yard. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, and other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Ashuwilticook Bike Trail is across the street. Whitney's Farm stand nearby with fresh Produce and Deli .

Berkshires Home Closed to Williams College

Welcome to our peaceful sanctuary with beautiful views of distant rolling hills and mountain views. Come to relax or come to explore all of the Berkshires activities. Get active w/ the many hiking trails, charming towns, arts and performances and a year-round ski resort for outdoor fun. Mt Greylock, Ramblewild Adventures, Mass MoCA, Tanglewood, Jiminy Peak for a great Berkshires experience. This house is the ultimate retreat for relaxation after exploring all of Berkshires best!

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook (not a kitchen) outside the bedroom. Small outdoor sitting area. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. The Annex is attached to the main house but is completely private.

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.