Holiday Homes in Western Massachusetts

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Featured Holiday Homes in Western Massachusetts

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"We enjoyed our stay. Excellent location to explore Western Mass!"
The price is AU$350
includes taxes & fees
28 Oct - 29 Oct
Berkshire Village Carriage House - Super Private!!

Cozy Home in Holyoke with 3 bedrooms

9.6 out of 10, Exceptional, (9)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
The price is AU$487
includes taxes & fees
16 Oct - 17 Oct
Cozy Home in Holyoke with 3 bedrooms

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (69)
"This was our second time staying here and we had a great time!"
The price is AU$423
includes taxes & fees
8 Oct - 9 Oct
The Creation Station is a cozy place so make yourself at home.

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
The price is AU$636
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AU$403
includes taxes & fees
5 Nov - 6 Nov
Home in Great Barrington

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.4 out of 10, Exceptional, (16)
"Great overnight stay! "
The price is AU$408
includes taxes & fees
8 Oct - 9 Oct
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Button's Modern Luxury Walkup Downtown Northampton

10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
The price is AU$770
includes taxes & fees
3 Nov - 4 Nov
Button's Modern Luxury Walkup Downtown Northampton

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (37)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is AU$307
includes taxes & fees
8 Oct - 9 Oct
Lovely 2nd Floor Apartment

Townhouse with Pool Table - Renovated w/ King Bed

10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
The price is AU$577
includes taxes & fees
12 Oct - 13 Oct
Townhouse with Pool Table - Renovated w/ King Bed

Newly Beautiful renovated first floor apartment getaway

8.0 out of 10, Very good, (2)
"We had an amazing time. This property was easy to find and very close to aloy of restaurants and shops! We had amazing chinese food! The apartment felt very homey. I love that it wasnt echo-y like past places I have stayed! I met Rose, the host, and she was super nice. She was very responsive and explained everything I needed to know before I arrived at the property. Also she lives near by and can address any problems or concerns you may have. The photography on the walls were gorgeous, the...
The price is AU$526
includes taxes & fees
8 Oct - 9 Oct
Newly Beautiful renovated first floor apartment getaway

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is AU$609
includes taxes & fees
4 Nov - 5 Nov
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$724
includes taxes & fees
8 Oct - 9 Oct
Comfortable Berkshires retreat on mtn resort, SISO

PICON COZY

7.4 out of 10, Good, (69)
"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 AU$254
includes taxes & fees
20 Oct - 21 Oct
PICON COZY

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

8.8 out of 10, Excellent, (3)
"Overall great spot and very clean. Lots of space to accommodate large groups, and the listing is transparent. The only reason I took off 1 star is all of the beds were very stiff and uncomfortable, which unfortunately would keep me from rebooking. However, if that doesn’t bother you, this place is a great little spot to stay the night if you’re in the area. "
The price is AU$541
includes taxes & fees
16 Oct - 17 Oct
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "
The price is AU$519
includes taxes & fees
27 Oct - 28 Oct
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AU$767
includes taxes & fees
20 Oct - 21 Oct
Cheerful 3-bedroom cottage with woodstove

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (4)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is AU$729
includes taxes & fees
13 Oct - 14 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
8.0 out of 10, Very good, (5)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AU$741
includes taxes & fees
8 Oct - 9 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

North Getaway Cottage

9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AU$800
includes taxes & fees
2 Nov - 3 Nov
North Getaway Cottage
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

Find out more about Western Massachusetts

Find out more about Western Massachusetts

Western Massachusetts Holiday Homes information

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