Holiday Homes in Western Massachusetts

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Featured Holiday Homes in Western Massachusetts

Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
PICON COZY
7.8 out of 10, Good, (48)
"Loved it"
The price is AU$250
includes taxes & fees
17 Oct - 18 Oct
PICON COZY
Historic Farmhouse Near Mountains & Colleges!
10.0 out of 10, Exceptional, (1)
"Stayed here with my husband and a few friends. Great place, listed as described. The beds were so comfty. Easy to get to the Big E and there was a beautiful disc golf course literally right next door. We loved watchig from the back porch! Would recommend!!"
Historic Farmhouse Near Mountains & Colleges!
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (89)
"We were attending a horse show locally. We stayed a few nights and everything about this day was easy from start to finish."
The price is AU$308
includes taxes & fees
15 Oct - 16 Oct
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is AU$741
includes taxes & fees
8 Oct - 9 Oct
Cheerful 3-bedroom cottage with woodstove
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AU$770
includes taxes & fees
28 Oct - 29 Oct
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (21)
"This beautiful house was everything we were looking for. We felt at home as soon as we arrived. The home is beautiful and clean. The beds, towels, kitchen, kitchen supplies, rear screened in porch, living room, and bathrooms were all in excellent condition. We spent a lot of time sitting on the porch getting caught up and eating the meals prepared in the kitchen. We recommend this house for someone looking for a place to stay when enjoying the area. "
Stockbridge Home, Come Experience The Berkshires!
Private Home ~ Old World Charm, Modern Conveniences
10.0 out of 10, Exceptional, (12)
"Very pleased with the property. Just a short drive to many restaurants. "
Private Home ~ Old World Charm, Modern Conveniences
Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame
9.0 out of 10, Wonderful, (2)
"WiFi was perfect for kids and iPads. Thanks. The accommodations were roomy and clean. However, there were not enough tvs for gaming. We also didn’t have access to more garbage bags for cleaning or properly setting trash out. Family gatherings mean more food, more garbage and different age ranges. TVs for gaming is a plus. WiFi was"
The price is AU$1,583
includes taxes & fees
6 Oct - 7 Oct
Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (214)
"My wife and I were in town for a wedding and decided to make a weekend out of it. This carriage house was everything we could've hoped for and more! It had everything we needed (kitchen, dishwasher, coffeemaker, full bathroom, TV, etc.) as well as a great decor that reflected a Berkshires getaway. The space was clean, organized, and easy to use. Christopher was extremely responsive, immediately addressed all our questions, and even offered to ship me back my Hydro Flask water canteen that I...
Berkshire Village Carriage House - Super Private!!
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (127)
"We planned a family reunion in the area. The farm house was pet friendly and the perfect location to our family that lived 20 minutes away. Eric was very accommodating. It was quiet and relaxing."
The price is AU$569
includes taxes & fees
15 Oct - 16 Oct
Big farmhouse in the foothills of the Berkshires
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Springfield home with a view(Private first floor)
9.0 out of 10, Wonderful, (6)
"We enjoyed our stay in this cozy home. Only issue was the listing says there’s 3 bedrooms (accurate) and 2 rooms with futons in them, but there was a couch in the den and a small couch in the living room, not really beds. Listing could use some more updated, accurate photos to show how it’s clearly a lived in house and not a full time rental."
The price is AU$547
includes taxes & fees
5 Oct - 6 Oct
Springfield home with a view(Private first floor)
Amherst, Perfect Location, UMass, Smith, MHC!
10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (34)
"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (103)
"We have 2 dogs who travel with us. So renting pet friendly homes is a much better option than a hotel room. The house was clean, comfortable, and the fenced in yard was great for our dogs. Nice big bath towels (my favorite) and a nicely stocked kitchen made staying at this house very enjoyable. An added bonus were two sets of dog-loving neighbors who came out to greet us and say hello to our pups. Thanks Julie for providing a welcoming place to stay for our weekend getaway."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (64)
"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
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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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Other property types in Western Massachusetts

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1717)
"Very nice place, big spacious room, great views of the mountains."
The price is AU$283
includes taxes & fees
6 Oct - 7 Oct
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (898)
"Was good everything "
The price is AU$216
includes taxes & fees
16 Oct - 17 Oct
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.