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Western Massachusetts Holiday Rentals

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Check prices for these dates

Tonight
20 Dec - 21 Dec
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21 Dec - 22 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

Our top choices for Western Massachusetts holiday rentals

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Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2181)
"Awesome for ski"
United States
Lazar
The price is HK$809
HK$989 total
includes taxes & fees
19 Jan - 20 Jan 2026
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,704
HK$1,903 total
includes taxes & fees
20 Jan - 21 Jan 2026
Jiminy Peak Mountain Resort
Fridge, microwave, oven, stovetop
Serene 1-bedroom suite on 65 acre horse property

Serene 1-bedroom suite on 65 acre horse property

Serene 1-bedroom suite on 65 acre horse property
Belchertown
10.0 out of 10, Exceptional, (23)
"A great jumping off point for the Pioneer Valley and 5 colleges. Brent and Claire were wonderful hosts! Nice and quiet on the property, and it’s a neat experience to have the beautiful horses right outside your window. "
United States
Claire W.
The price is HK$778
HK$1,612 total
includes taxes & fees
22 Dec - 23 Dec
Serene 1-bedroom suite on 65 acre horse property
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.4 out of 10, Very good, (9)
"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."
United States
Matthew H.
The price is HK$615
HK$1,165 total
includes taxes & fees
21 Dec - 22 Dec
Tiny Home with AC and WiFi in lovely Ludlow
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is HK$903
HK$1,574 total
includes taxes & fees
30 Dec - 31 Dec
Lovely 2nd Floor Apartment
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is HK$1,205
HK$2,006 total
includes taxes & fees
12 Jan - 13 Jan 2026
Home in Great Barrington
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is HK$980
HK$2,498 total
includes taxes & fees
21 Dec - 22 Dec
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Dining
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is HK$980
HK$2,498 total
includes taxes & fees
26 Dec - 27 Dec
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,134
HK$2,910 total
includes taxes & fees
22 Dec - 23 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lanesborough
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is HK$1,050
HK$1,598 total
includes taxes & fees
22 Dec - 23 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
2.0 star property
Belchertown
9.4 out of 10, Exceptional, (22)
"Adorable spot. Great location. Clean, organized and well stocked. "
United States
Jen M.
The price is HK$1,226
HK$1,633 total
includes taxes & fees
21 Dec - 22 Dec
Newly Built Barn Loft in Pioneer Valley
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,430
HK$2,638 total
includes taxes & fees
23 Dec - 24 Dec
Florida Mountain Log Cabin
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
The price is HK$1,247
HK$3,009 total
includes taxes & fees
22 Dec - 23 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is HK$504
HK$1,606 total
includes taxes & fees
21 Dec - 22 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Property grounds
The Creation Station is a cozy place so make yourself at home.

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

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,401
HK$2,156 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Creation Station is a cozy place so make yourself at home.
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (12)
"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."
United States
Eric W.
The price is HK$1,012
HK$2,503 total
includes taxes & fees
21 Dec - 22 Dec
Cozy Home in Holyoke with 3 bedrooms
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is HK$786
HK$2,106 total
includes taxes & fees
12 Jan - 13 Jan 2026
Charming Chicopee Getaway
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is HK$1,012
HK$2,077 total
includes taxes & fees
21 Dec - 22 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Property grounds
Welcome to Honey Spot!

Welcome to Honey Spot!

Welcome to Honey Spot!
Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is HK$1,012
HK$2,295 total
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome to Honey Spot!
Private kitchen
Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (1)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is HK$1,082
HK$1,589 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy 2-bedroom apartment in Chicopee
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

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