Search Condo Rentals in Western Massachusetts

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Western Massachusetts condo rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2168)
"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 AED 382
AED 467 total
includes taxes & fees
4 Jan - 5 January 2026
Vacation Village in the Berkshires
Property grounds
Welcome to Honey Spot!

Condo in 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 AED 477
AED 1,092 total
includes taxes & fees
31 Dec - 1 January 2026
Welcome to Honey Spot!
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in 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 AED 503
AED 1,243 total
includes taxes & fees
15 Dec - 16 Dec
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is AED 1,025
AED 1,973 total
includes taxes & fees
24 Dec - 25 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo in Hancock

9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is AED 503
AED 1,104 total
includes taxes & fees
15 Dec - 16 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

Condo in 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 AED 459
AED 1,545 total
includes taxes & fees
31 Dec - 1 January 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

Condo in Dover

8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is AED 261
AED 1,035 total
includes taxes & fees
16 Dec - 17 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

Condo in West Dover

9.0 out of 10, Wonderful, (44)
"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 AED 364
AED 1,129 total
includes taxes & fees
23 Dec - 24 Dec
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Private kitchen
Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Condo in Wilmington

10.0 out of 10, Exceptional, (1)
"Beautiful condo that is spacious in a quiet spot"
United States
Linda
The price is AED 1,322
AED 2,386 total
includes taxes & fees
11 Dec - 12 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)

Condo in Dover

9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
United States
Mary C.
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Property grounds
2BR Loft With Views | Ski-In Access

Condo in West Dover

The price is AED 1,708
AED 2,128 total
includes taxes & fees
11 Dec - 12 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

Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown

10/10 Excellent
"Everything was great. Staff was awesome "
Robert 1-night trip
Posted 1 day ago
Hampton Inn & Suites Springfield/Downtown

Frequently asked questions

How much do condos in Western Massachusetts cost?
Condos in Western Massachusetts range from AED 467 to AED 2,386 per night. These properties offer loads of space for your whole crew at a price that won't stretch the budget. These prices were 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?
Western Massachusetts has 48 condos to pick from. Enter your destination and travel dates and book your perfect stay today.
Why book your condo in Western Massachusetts with Expedia?
Booking a condo in Western Massachusetts is as easy as working out your travel dates and choosing a place that meets your needs. In search of something luxurious or low cost, or a stay that also comes with a kitchen? Use Expedia's search filters to narrow your results even further and find your ideal match.
How can I find cheap condos in Western Massachusetts?
Expedia can help you narrow your search for cheap condos in Western Massachusetts. To lock in a fantastic stay in a couple of quick clicks, try out the filter tool to tailor your search results by amenities, budget and star rating.

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