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Search and Rent Western Massachusetts Condos

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Our top choices for Western Massachusetts condo 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, (2182)
"Awesome for ski"
United States
Lazar
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Village in the Berkshires
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.
$260 nightly
The price is $295
Dec 31 - Jan 1, 2026
Total with taxes and fees
Welcome to Honey Spot!
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$317 nightly
The price is $354
Dec 24 - Dec 25
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Outdoor dining
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in Hancock

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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.
$301 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Jan 6 - Jan 7, 2026
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
4 bedrooms, iron/ironing board, WiFi, bed sheets
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Condo in Enfield

Spacious 4-bedroom condo with AC and WiFi in charming 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.
$372 nightly
The price is $421
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Lobby
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$406 nightly
The price is $459
Jan 21 - Jan 22, 2026
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Beach
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$272 nightly
The price is $307
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Interior
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Condo in Dover

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
9.4 out of 10, Exceptional, (18)
"Property was perfect for proximity to the mountain, restaurants and stores. Perfect family spot for a ski vacay!"
United States
amy
$930 nightly
The price is $1,051
Dec 24 - Dec 25
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Terrace/patio
2BR Loft With Views | Ski-In Access

Condo in West Dover

2BR Loft With Views | Ski-In Access
$1,024 nightly
The price is $1,130
Dec 24 - Dec 25
Total with taxes and fees
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
Brandon 3-night trip
Posted 16 hours ago
The Yankee, Trademark Collection by Wyndham

Find out more about Western Massachusetts

Western Massachusetts Condo Rentals information

Number of reviews
2,289
Accommodation
48 Condo Rentals
Lowest Price
$141
Highest Price
$1,130

Frequently asked questions

How much do condos in Western Massachusetts cost?
Condos in Western Massachusetts range from $141 to $1,130 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.
What is there to do in Western Massachusetts near my condo?
The best accessory to take on your Western Massachusetts adventure is a good itinerary! Titanic Museum, Springfield Armory and Springfield City Library are among the leading things to do if you're heading to Springfield. West Springfield also has lots of fantastic attractions, such as Big E. Want to explore more? Find time for Eastern States Exposition and Olympia Ice Center too.

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