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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Western Massachusetts condo rentals

Exterior

1. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
$256 nightly
The price is $286
Nov 8 - Nov 9
Total with taxes and fees
Work, Play & Stay! Apt Near Holyoke Medical Center
A modern kitchen with dark cabinets, a granite countertop, a built-in oven, a microwave, and a large window providing natural light.

2. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
$433 nightly
The price is $484
Nov 8 - Nov 9
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

3. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (18 reviews)
"lovely place to stay"
United States
Nancy P.
$497 nightly
The price is $555
Nov 7 - Nov 8
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
A calm lake with a wooden boat on the shore.

4. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$248 nightly
The price is $280
Nov 15 - Nov 16
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

5. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$316 nightly
The price is $357
Nov 7 - Nov 8
Total with taxes and fees
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

6. Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex

Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
$365 nightly
The price is $413
Nov 8 - Nov 9
Total with taxes and fees
Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
A kitchen counter with a bottle of Cabernet Sauvignon, a feedback card, and a basket of fruits.

7. Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8

Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Great location, comfortable and spacious living room and bedrooms. "
United States
Emma C.
$459 nightly
The price is $518
Nov 10 - Nov 11
Total with taxes and fees
Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8
Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

8. Expansive 2BR | Sleeps 10 | Ski-In

Expansive 2BR | Sleeps 10 | Ski-In
West Dover
$536 nightly
The price is $591
Nov 9 - Nov 10
Total with taxes and fees
Expansive 2BR | Sleeps 10 | Ski-In
Gather around the glowing fire pit and unwind under the open sky, the perfect way to end a day of adventure.

9. 2BR Loft With Views | Ski-In Access

2BR Loft With Views | Ski-In Access
West Dover
$578 nightly
The price is $637
Nov 9 - Nov 10
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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Learn more about Western Massachusetts

Rolling hills and charming towns define this picturesque region, where art lovers flock to MASS MoCA in North Adams. Outdoor enthusiasts can hike Mount Greylock, while history buffs explore Norman Rockwell's studio in Stockbridge.

See all hotels in Western Massachusetts
A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.

Top reviews in Western Massachusetts

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
Egremont

10/10 Excellent

So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
United States
Emily
Reviewed July 7, 2025
Prospect Berkshires

Frequently Asked Questions

How much do condos in Western Massachusetts cost?

Condos in Western Massachusetts range from $280 to $637 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 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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