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Western Massachusetts Vacation Rentals

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Check prices for these dates

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Dec 27 - Dec 28
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Dec 28 - Dec 29
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Jan 2 - Jan 4
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Jan 9 - Jan 11

Our top choices for Western Massachusetts vacation rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is ￥16,234
￥19,847 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
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 ￥33,511
￥37,431 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Jiminy Peak Mountain Resort
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is ￥18,178
￥31,499 total
includes taxes & fees
Dec 28 - Dec 29
Lovely 2nd Floor Apartment
Exterior
Tiny Home with AC and WiFi in lovely Ludlow

Vacation Home in Ludlow

Tiny Home with AC and WiFi in lovely 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 ￥12,335
￥23,371 total
includes taxes & fees
Dec 28 - Dec 29
Tiny Home with AC and WiFi in lovely Ludlow
Fridge, microwave, oven, stovetop
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Vacation Home in Boston Road

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is ￥19,728
￥50,269 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Property grounds
Welcome to Honey Spot!

Condo in Pine Point

Welcome to Honey Spot!
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 ￥20,298
￥46,058 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Welcome to Honey Spot!
Smart TV, books, stereo
Newly Built Barn Loft in Pioneer Valley

Apartment in Belchertown

Newly Built Barn Loft in Pioneer Valley
2.0 star property
9.4 out of 10, Exceptional, (22)
"Adorable spot. Great location. Clean, organized and well stocked. "
United States
Jen M.
The price is ￥24,592
￥32,596 total
includes taxes & fees
Dec 28 - Dec 29
Newly Built Barn Loft in Pioneer Valley
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 ￥22,765
￥58,391 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms

Vacation Home in Holyoke

Cozy Home in Holyoke with 3 bedrooms
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 ￥20,298
￥50,580 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy Home in Holyoke with 3 bedrooms
Property grounds
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
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 ￥28,105
￥43,254 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
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 ￥21,079
￥32,416 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥23,608
￥40,148 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Home in Great Barrington
Dining
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Vacation Home in Boston Road

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is ￥19,674
￥50,131 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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 ￥25,014
￥61,253 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
TV
Florida Mountain Log Cabin

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥31,970
￥57,082 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Florida Mountain Log Cabin
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
9.0 out of 10, Wonderful, (4)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥13,950
￥37,445 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Apartment in Chicopee

Charming Chicopee Getaway
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 ￥17,800
￥46,058 total
includes taxes & fees
Dec 29 - Dec 30
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Apartment in Amherst

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.2 out of 10, Wonderful, (19)
"Great property! Thank you for a wonderful stay."
United States
David
The price is ￥34,991
￥65,594 total
includes taxes & fees
Dec 30 - Dec 31
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Private kitchen
Welcoming 3-bedroom house- Gardner home

Vacation Home in Chicopee

Welcoming 3-bedroom house- Gardner home
2.0 star property
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is ￥18,737
￥52,790 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Welcoming 3-bedroom house- Gardner home
Fridge, microwave, oven, stovetop
Newly Beautiful renovated first floor apartment getaway

Vacation Home in Forest Park

Newly Beautiful renovated first floor apartment getaway
8.8 out of 10, Excellent, (3)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is ￥27,122
￥54,685 total
includes taxes & fees
Dec 28 - Dec 29
Newly Beautiful renovated first floor apartment getaway
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

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