Holiday Homes in Western Massachusetts

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Featured Holiday Homes in Western Massachusetts

Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, 35 reviews
"Very clean and nice apartment in a pleasant little city."
The price is AU$387
includes taxes & fees
7 July - 8 July
Cozy apartment located in quiet Williamsburg
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, 53 reviews
"Beautiful place, we stayed here after our Six Flags birthday trip and the boys loved the pool and hot tub and the whole atmosphere! 10/10!!!"
The price is AU$417
includes taxes & fees
29 July - 30 July
The Creation Station is a cozy place so make yourself at home.
PICON COZY
8.0 out of 10, Very good, 44 reviews
"Perfect little house 20 minutes from six flags. Bathroom looks like it was recently updated as well as kitchen appliances. it's a little dated but who cares the price was right. Much more relaxing and comfy than a hotel room."
The price is AU$257
includes taxes & fees
7 July - 8 July
PICON COZY
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1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, 61 reviews
"This stay is one of the best I have enjoyed using VRBO! From start to finish it was seamless. We loved that the house was historic and the renovation was amazing!! The moment we walked inside we were at home. Some amenities, like the portacrib available, weren’t even listed. The owners thought of everything. Communication with the owner was excellent. The house itself is wonderfully decorated, stocked with everything you could possibly need and comfortable. Our family used all three levels and...
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, 4 reviews
"We had a lovely time. We enjoyed the pool. We did appreciate the fully appointed kitchen as we did cook our dinners there."
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 16 reviews
"The location of this lovely home was amazing. We thoroughly enjoyed our visit! The setting was just beautiful, and there were plenty of games, puzzles, and cozy spots for indoor entertainment as well."
Private Lake House in the Berkshires
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, 2 reviews
"This was our second stay at David’s property. So clean and welcoming! Quiet, in a residential neighborhood and just what we needed while visiting the area. Thank you David!"
The price is AU$303
includes taxes & fees
7 July - 8 July
Lovely 2nd Floor Apartment
Luxury Vacation Rental in the Berkshires!
10.0 out of 10, Exceptional, 5 reviews
"The house and the view over the expansive lawn facing the mountains was beautiful. The outside stone patio and gardens were a wonderful place to sit and relax. Everything needed for cooking meals was available along with all the comfortable areas inside the house made for a perfect vacation!"
Luxury Vacation Rental in the Berkshires!
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, 82 reviews
"The property was exactly as listed. Lee was easy to communicate with and everything went smoothly."
The price is AU$316
includes taxes & fees
15 July - 16 July
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 70 reviews
"We enjoyed our stay, although we basically only slept and ate breakfast at the house (we were attending Solid Sound at MASS MoCA). Very clean, quiet, spacious, and comfy beds. My husband and 9-year-old loved the hot tub. The only quibble we had was the air fresheners (too many and too strongly-scented) but that was easily remedied by unplugging them."
Hearts Desire is a furnished whole house in a small, colorful garden center.
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, 14 reviews
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Private Suite with a Sweet View. Spacious, close to town, dog friendly
10.0 out of 10, Exceptional, 25 reviews
"We liked the fact that it was very quiet, perfectly described, had an amazing view and was beyond peaceful. The gardens and landscape made the setting even better. Wished we were in the area longer so we could’ve stayed longer. Would definitely book this suite again. "
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, 60 reviews
"This was the 2nd time we have rented this property and again it did not disappoint. The location on the mountain is beautiful. The check in/check out process was easy. The host (Howie) responds to any questions very quickly and enthusiastically. Perfect place for a family with spacious bedrooms, nice kitchen, back deck with grill. Looking forward to going back"
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Hot tub, canoe, dog-friendly/family friendly cottage in the Berkshires!!
10.0 out of 10, Exceptional, 1 review
"Absolutely loved it. Perfect getaway when the city is too noisy. Awesome location in the woods surrounded by nothing but forest. If you plan on staying outside in the hot tub, maybe get one of those bug repellent tiki torches however i got no other complaints. Maybe a tv in the adult bedroom? Anyway good kitchen good bathroom good living room good bedroom for adults good room for children. If youre looking to get away, there isnt anything wrong in picking this place if you desire a forest get...
Hot tub, canoe, dog-friendly/family friendly cottage in the Berkshires!!
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 8 reviews
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Peace and quiet on the lake
9.6 out of 10, Exceptional, 187 reviews
"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"
Peace and quiet on the lake
Berkshire Lake access
10.0 out of 10, Exceptional, 42 reviews
"Everything about this was easy and convenient, from communication with Joni to its sweet location just steps from a lake. My family of four were plenty comfortable with 3 bedrooms and 2 bathrooms, and the kitchen had everything we needed. We would stay again!"
Berkshire Lake access
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
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See all available properties in Western Massachusetts
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.

Other property types in Western Massachusetts

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 865 reviews
"Nice location, well kept up."
The price is AU$276
includes taxes & fees
7 July - 8 July
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, 1,679 reviews
"It was so nice and Awsome for the baby "
The price is AU$291
includes taxes & fees
8 July - 9 July
Vacation Village in the Berkshires
Peace and quiet on the lake
9.6 out of 10, Exceptional, 187 reviews
"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"
Peace and quiet on the lake
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.

Western Massachusetts Holiday Homes information

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