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Check prices for these dates

In two weeks
19 Dec - 21 Dec
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Featured Condo Rentals in Western Massachusetts

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Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2163)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is AU$167
includes taxes & fees
7 Dec - 8 Dec
Vacation Village in the Berkshires
Property grounds
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 AU$455
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome to Honey Spot!
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock
8.0 out of 10, Very good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
The price is AU$514
includes taxes & fees
8 Dec - 9 Dec
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is AU$822
includes taxes & fees
19 Dec - 20 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is AU$462
includes taxes & fees
8 Dec - 9 Dec
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Microwave, oven, stovetop
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Enfield
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
The price is AU$644
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is AU$431
includes taxes & fees
8 Dec - 9 Dec
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover
9.0 out of 10, Wonderful, (43)
"We were unable to stay as when we went in the condo, we found the condo damp, musty, dusty, very worn, extremely outdated and uncomfortable. We left and found different accommodations for the weekend at Chateau 239 which I highly recommend. "
United States
Diana W.
The price is AU$565
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Private kitchen
Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Wilmington
10.0 out of 10, Exceptional, (1)
"Beautiful condo that is spacious in a quiet spot"
United States
Linda
The price is AU$993
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Property grounds
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Dover
9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
United States
Mary C.
The price is AU$926
includes taxes & fees
8 Dec - 9 Dec
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Property grounds
2BR Loft With Views | Ski-In Access

2BR Loft With Views | Ski-In Access

West Dover
The price is AU$852
includes taxes & fees
8 Dec - 9 Dec
2BR Loft With Views | Ski-In Access
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

Hotel UMass

Hotel UMass

10/10 Excellent
"Everything was great. Nice pastries. So convenient. "
Ieva 2-night trip
Posted 3 days ago
Hotel UMass

Find out more about Western Massachusetts

Western Massachusetts Condo Rentals information

Number of reviews
2,266
Accommodation
48 Condo Rentals
Lowest Price
AU$167
Highest Price
AU$993

Frequently asked questions

How much do condos in Western Massachusetts cost?
You can expect to pay from AU$167 to AU$993 per night for condos in Western Massachusetts. No matter your budget, an epic stay is a click away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Western Massachusetts?
Take your pick of 48 condos in Western Massachusetts. Whether you're on a trip with the whole family or your besties, and wherever you're off to, Expedia makes it a breeze to find the perfect hotel.
What is there to do in Western Massachusetts near my condo?
Whatever your interests, there are tons of things to do in Western Massachusetts. If you're on your way to Springfield, stop by Naismith Memorial Basketball Hall of Fame, Titanic Museum and Springfield Science Museum. Planning to stay in Amherst? Emily Dickinson Museum, Amherst Farm Winery and Mead Art Museum are among the top sights in this city.

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