Alyssa has been writing about exciting travel topics for Trips to Discover since 2013. After living the big city life in Chicago, Washington, DC, and Atlanta, Alyssa sold the bulk of her possessions and became a digital nomad, living full-time in her camper and working from wherever she could find an outlet and an internet connection for her laptop.
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The mountainous areas of western Massachusetts known as the Berkshires is a popular vacation destination for family fun and romantic getaways. The colorful fall foliage always draws in lots of crowds, as well as the many farmers’ markets, fun festivals, and fantastic skiing opportunities at other times of the year. For private, cozy, and relaxing accommodations that feel like home, consider booking one of these lovely Airbnbs in the Berkshires.
You can have this entire house to yourself with up to 10 people and enjoy its four bedrooms and two baths. The home is on seven acres of woods and has a large lawn and perennial gardens. It’s a family-friendly space that’s a 10-minute walk to a lake and perfect for groups with children. A short drive will get you to everything the Berkshires has to offer while you have lots of privacy and outdoor recreation here, such as swimming, boat access, and fishing. Guests can use the host’s library of books, canoe, and kayak. Pets are not allowed at this home.
This house accommodates up to eight guests in the Monterey area and has three bedrooms and two baths. It’s up the hill from Lake Garfield and offers lovely lake views. People who stay here enjoy the sunsets, fast Wi-Fi, and wooded seclusion. It’s an ideal place to stay to see the fall foliage, ski at Ski Butternut, swim, kayak, hike, and gaze at the stars. From here, it’s easy to visit Jacob’s Pillow, the Norman Rockwell Museum, Berkshire Theater Festival, and other local attractions. The living space and kitchen are accessed by stairs, and a 4WD vehicle is recommended for winter stays because of the twisty driveway.
Large groups up to 15 people can stay at this five-bedroom, 4.5-bath cabin to enjoy a tranquil vacation in the Berkshires. It’s about 15-20 minutes from Great Barrington and the Butternut Ski Mountain. The Appalachian Trail and Tyringham Cobble Park are each just 10 minutes from here for outdoor recreation. It’s nice and warm in here in the winter with a wood-burning stove, and the home also has 5G Wi-Fi. Other features of the space include a coffeepot, latte maker, A/C units, portable fans, dimmable lights, laundry machines, and easy parking.
For an affordable and more social place to stay in the Berkshires, choose this private room in a house for up to four guests. It is surrounded by nature and a rustic retreat in rural Sandisfield, yet close to restaurants and attractions too. There are actually two bedrooms for rent on Airbnb here. Breakfast is included with your stay, and guests can generally use the kitchen and enjoy the screened porch and large deck. There’s also a wooded private backyard here. Children are welcome, and a port-a-crib is available upon request. Your hosts love to cook and can even make you dinner, as well as arrange for bike and ski rentals or pick you up at the bus stop.
Rent this cabin for up to six people in Monterey and enjoy three bedrooms and three baths all to yourself. The cabin is next to a stream and offers sounds of rushing water to lull you to sleep. It’s five minutes from Butternut Ski Mountain and 10 minutes to Great Barrington. This is a very private place to stay where you’ll have access to the whole property. Sleeping arrangements are in two bedrooms and a king loft above. Onsite amenities include laundry machines, free parking, and cooking basics.
Another great place for large groups is this house for up to 10 people in Otis. It has three bedrooms, six beds, and three baths. Other features are the two-level, wrap-around deck, swing set that kids love, and the Audubon preserve behind the house. Dogs are allowed here for a fee. When you stay here, you can use the gas BBQ grill on the deck, free Wi-Fi, and DVD collection onsite for movies. The home is not air-conditioned but you can easily stay cool with the screened windows, ceiling fans, and open skylights.
It’s also nice to stay in this studio apartment that accommodates up to three guests in Sandisfield. It has many windows to let the natural light in and welcomes long-term guests. It’s located down a mile-long gravel road and offers easy access to hiking on the local trails. The space has a separate entrance from a private deck at one end of the home. The owner lives in the main house but there are empty rooms between that part and the apartment for privacy. This is a four-season destination with pristine lakes and forests and popular cultural events in the area. Well-behaved dogs, up to two max, are allowed for $10 per dog.
Guests love this house for up to eight guests in Otis to visit all the local Berkshires attractions. It has four bedrooms and two baths and offers open living and dining room areas, as well as a loft upstairs and kitchen for cooking meals. It also has laundry machines in the basement, Wi-Fi, and Direct TV. Come here for a quiet stay and lots of natural beauty as you stay on the backside of the Otis Ridge Ski Area.
A Great Barrington Airbnb worth looking into is this one that works well for up to nine guests. It has four bedrooms and two baths and is centrally located in Southern Berkshire County. It’s easy to ski, swim, hike, or just enjoy the views when you’re here. The Butternut ski area is 10 minutes away. The interior space has a chef’s kitchen, comfortable living areas for entertaining, and an open floor plan great room. There’s also a screened sunroom, lower deck with a hot tub and pergola, hammocks, and fire pit with chairs. The home is at the top of a long gravel road, so it’s good to have a 4WD vehicle when staying here in the winter.
In Monterey, Massachusetts, this Berkshires destination accommodates four guests in two bedrooms and 1.5 baths. It’s a classic New England Cape-style home that’s ideal for a family of four or two couples. The space is bright and open, with a fireplace and screened porch for relaxing. There’s a sunroom for gathering and front and back lawns for relaxing and having good conversations. Laundry machines are in the basement, and there’s a hammock on the porch to take a relaxing break.
This is definitely one of the most unique Airbnbs to rent in the Berkshires and a highly rated chalet for up to four guests. It has a wood-burning fireplace, a large deck off the back, a grill, and an outdoor seating area. The home also has Wi-Fi and a fully stocked kitchen if you want to cook your own meals. There are three skiing areas and great hiking in the vicinity. Long-term stays are welcome here in addition to quick getaways in the mountains.
The Berkshires area is home to many wonderful cabins of varying sizes that you can rent on Airbnb. This one can sleep up to nine people and has four bedrooms and two baths. It has two fireplaces, an outdoor hot tub, and is on a lovely property with a brook. There’s a great kitchen here for preparing meals, and guests are welcome to eat at the beautiful dining room table or on the covered deck that overlooks the woods. The garage is available for guest use as well as the trail that leads down to the brook. Your host offers beach chairs, towels, and an umbrella to use as well.