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Featured Condo Rentals in Western Massachusetts

Our top choices for Western Massachusetts condo rentals

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1967)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$203
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

8.0 out of 10, Very good, (1)
"very nice and roomy! really enjoyed."
The price is AU$466
includes taxes & fees
23 Sept - 24 Sept
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

10.0 out of 10, Exceptional, (40)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very good, (7)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is AU$514
includes taxes & fees
15 Sept - 16 Sept
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
The price is AU$482
includes taxes & fees
22 Sept - 23 Sept
UNIQUE - 1BR Country Condo @ Jiminy Peak

Walk to Ski Slopes: Jiminy Peak Resort Getaway!

10.0 out of 10, Exceptional, (14)
"Great condo - "
Walk to Ski Slopes: Jiminy Peak Resort Getaway!

Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

7.0 out of 10, Good, (9)
"Mostly a great stay. The AC which was advertised as an amenity did NOT work. The host did not come to fix it when I complained. Also, no extra blankets or sheets, no hand soap in bathroom or kitchen. We bought and left soap for the next guests. Great kitchen equipment!"
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

10.0 out of 10, Exceptional, (1)
"You'll love this house, it feels just like home but more relaxing and enjoyable! We used the community heated pool and hot tub several times during our stay. The house is just as pictures, but better. Everything you could need is supplied n the rental, all you need is food and clothes. We slept great at this house, better than any other vacation, no one got up early. The kitchen and grill were great to cook with. Staying at this house was very enjoyable!"
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!

2.0 star property
10.0 out of 10, Exceptional, (12)
"Everything was great. We enjoyed our stay!"
Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

9.0 out of 10, Wonderful, (27)
"We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. "
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

10.0 out of 10, Exceptional, (6)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

10.0 out of 10, Exceptional, (32)
"Everything was spot on. Will be back!!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

9.6 out of 10, Exceptional, (17)
"Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!"
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

10.0 out of 10, Exceptional, (12)
"We'll be back!"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

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"
Welcome to Honey Spot!

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Club Wyndham Bentley Brook Resort - 2 Bedroom

6.0 out of 10, (2)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
Club Wyndham Bentley Brook Resort - 2 Bedroom
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

Frequently asked questions

How much do condos in Western Massachusetts cost?
You can expect to pay from AU$203 to AU$514 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 71 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.