The Berkshires showing snow as well as a family

Holiday Homes in Western Massachusetts

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Featured Holiday Homes in Western Massachusetts

Situated in a grassy yard, this charming house features a sloped roof, chimney, and a small window.

"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"

Relax on the covered porch with a comfortable seating area and beautiful views.

"The house and location were perfect. Comfortable beds! Would definitely stay again"

5 bedrooms, iron/ironing board, WiFi, bed sheets

includes taxes & fees

31 July - 1 Aug

Relax in a serene space with a comfortable armchair, console table, and lush greenery.

"Easy stay, good location for us. Would stay again. "

includes taxes & fees

30 July - 31 July

Experience the perfect blend of traditional and contemporary style in this inviting space, featuring a plush sofa, wooden coffee table, and modern kitchen.

"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"

Enjoy cooking and dining with a large dining table and modern kitchen amenities.

"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."

Relax in this spacious living room with a high ceiling, featuring a sofa, armchair, and coffee table.

"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."

Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

"Highly recommend this charming, historic place. Well appointed. Has everything you need for your stay. Cozy…yet plenty of space for everyone. Looks like it was just renovated. Took my daughter and two granddaughters for a ski weekend. Wouldn’t hesitate to come back here. "

Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

"Very friendly hosts, great location. "

Relax in style with a comfortable sofa, tufted armchair, and sleek coffee table.

"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "

includes taxes & fees

31 July - 1 Aug

Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."

includes taxes & fees

27 July - 28 July

Relax in a spacious living area with a high ceiling and large windows offering views of the surrounding greenery.

"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."

Relax in this spacious living room with a high ceiling, leather sofa, and wooden coffee table.

"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...

Enjoy meals in the kitchen with a dining area featuring a table and chairs.

"We stayed for a guys hunting trip and the place was what we needed after a long day"

Enjoy cooking in this well-equipped kitchen with an oven and stainless steel range hood.

"We loved everything about this home! It fit us perfectly and we would love to rent it again!"

Meetings and gatherings take place in this elegantly designed room with a long table and comfortable seating.

"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "

"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."

includes taxes & fees

28 July - 29 July

Enjoy cooking in this fully equipped kitchen with a microwave, coffee maker, and refrigerator.

"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "

includes taxes & fees

28 July - 29 July

Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "