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Vacation Homes in Western Massachusetts

Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is ￥67,833
￥125,104 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 5-bedroom house in charming Lee with WiFi
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Situated in a grassy yard, this charming house features a sloped roof, chimney, and a small window.

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (17)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Bring Your Pet & Visit Springfield: Westfield Home
Relax on the covered porch with a comfortable seating area and beautiful views.

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.0 out of 10, (11)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home
Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is ￥17,501
￥30,326 total
includes taxes & fees
Aug 4 - Aug 5
Lovely 2nd Floor Apartment
Contemporary Berkshire Home with Views of Taconic Golf Course
Relax in this spacious living room with a high ceiling, featuring a sofa, armchair, and coffee table.

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Experience the perfect blend of traditional and contemporary style in this inviting space, featuring a plush sofa, wooden coffee table, and modern kitchen.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (45)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Charming Berkshires Retreat – Minutes to Williamstown
Enjoy cooking and dining with a large dining table and modern kitchen amenities.

Charming Berkshires Retreat – Minutes to Williamstown

6.0 out of 10, (2)
"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."
Charming Berkshires Retreat – Minutes to Williamstown
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Relax in style with a comfortable sofa, tufted armchair, and sleek coffee table.

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (31)
"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. "
The price is ￥30,148
￥50,620 total
includes taxes & fees
Aug 3 - Aug 4
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is ￥30,148
￥54,811 total
includes taxes & fees
Aug 3 - Aug 4
Big farmhouse in the foothills of the Berkshires
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Relax in a spacious living area with a high ceiling and large windows offering views of the surrounding greenery.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (36)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
19th c. Barn in the Berkshires
Relax in this spacious living room with a high ceiling, leather sofa, and wooden coffee table.

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (90)
"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...
19th c. Barn in the Berkshires
Art House! Spacious Getaway By Mass Moca
Meetings and gatherings take place in this elegantly designed room with a long table and comfortable seating.

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"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! "
Art House! Spacious Getaway By Mass Moca
Spacious Private Retreat Near Holyoke State Park!
Enjoy meals in the kitchen with a dining area featuring a table and chairs.

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!
Historic Farmhouse Near Mountains & Colleges!
Enjoy cooking in this well-equipped kitchen with an oven and stainless steel range hood.

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (9)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
Tiny Home with AC and WiFi in lovely Ludlow
1 bedroom, WiFi, bed sheets

Tiny Home with AC and WiFi in lovely Ludlow

8.0 out of 10, Very Good, (2)
"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."
The price is ￥11,908
￥22,562 total
includes taxes & fees
Aug 8 - Aug 9
Tiny Home with AC and WiFi in lovely Ludlow
PICON COZY
Enjoy cooking in this fully equipped kitchen with a microwave, coffee maker, and refrigerator.

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is ￥10,175
￥24,370 total
includes taxes & fees
Aug 13 - Aug 14
PICON COZY
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (80)
"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.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (9)
"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. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Western Massachusetts Hotel Reviews

Hotel UMass

Hotel UMass

10/10 Excellent
"Convenient to the conference we attended. Parking was easy, accommodations were comfortable, staff was helpful - stay was very pleasant all around. "
Jason 2-night trip
Posted 1 day ago
Hotel UMass