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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 43 Condo Rentals in Western Massachusetts with updated reviews, rates, and availability.

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1803)
"The property was clean and the staff very accommodated."
The price is AED 418
AED 507 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Beach

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

10.0 out of 10, Exceptional, (37)
"Family trip with kids. Condo is great. Excellent location with great views of the mountain. Everything you need is within walking distance. Beds are comfortable and owner supplied plenty of towels and linens. We will definitely be back next year. "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!
Fridge, microwave, stovetop, dishwasher

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"We were so impressed with the cleanliness of the home and the ease and comfort with which we were able to stay. Truly a lovely place and close to everything!"
Duplex w/ Fire Pit ~ 1 Mi to MGM Springfield!
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

7.2 out of 10, Good, (5)
"My friends and I planned a last minute trip to Jimmy Peak which is a great mountain for all types of skiers. The host was very communicative right away and made sure everything was ready and gave me information for not just the house but where to go into town. The house was very clean and very comfortable to stay at almost like a true “ home away from home”. The home is very cozy and brings a great vibe to the trip. Even after our stay the host made sure to stay in contact and make sure...
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
The price is AED 327
AED 1,104 total
includes taxes & fees
5 May - 6 May
UNIQUE - 1BR Country Condo @ Jiminy Peak
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

10.0 out of 10, Exceptional, (1)
"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
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (30)
"Had an amazing stay here! Place was exactly like the photos. Fireplace was perfect! Great places to hike around the area. Host was great with fast communication. "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Exterior

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

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

7.0 out of 10, Good, (6)
"This house was perfect for our family trip to Springfield. We were close to everything we needed, and Hana was always available and quick to respond to any questions we had. The interior of the home has been totally remodeled and super clean, with a great fenced in backyard--though it rained our whole trip so we didn't get an opportunity to enjoy the fire pit and outdoor seating. And it was great to have large smart TVs in both bedrooms and the living room, and even a few board games to play...
The price is AED 551
AED 1,288 total
includes taxes & fees
5 May - 6 May
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Exterior

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 at Jiminy Peak in the Country Inn
Exterior

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

9.4 out of 10, Exceptional, (22)
"All you need for a ski trip"
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Snow and ski sports

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

10.0 out of 10, Exceptional, (12)
"This property was clean, and in a wonderful location to the mountain and other amenities. Host was professional, kind and courtesy. This was our first experience with an Air B & B. Would rent this condo again. Thank you CP. "
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Fridge, microwave, oven, stovetop

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Berkshires Getaway < 1 Mi Skiing & Hiking!
Fridge, microwave, stovetop, dishwasher

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (12)
"Beautiful spot, great location right at the mountain! We had such a great time here!"
Berkshires Getaway < 1 Mi Skiing & Hiking!
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Exterior

Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds

9.6 out of 10, Exceptional, (18)
"We all had a great visit. Property fantastic. "
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Ski on ski off 1 Br loft condo in the village center with private gated parking
Fridge, microwave, oven, stovetop

Ski on ski off 1 Br loft condo in the village center with private gated parking

10.0 out of 10, Exceptional, (16)
"Clean and & comfortable, the location cannot be beat for a ski trip to Jiminy Peak! Jim (owner) was very communicative and great to work with!"
Ski on ski off 1 Br loft condo in the village center with private gated parking
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Living area

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

10.0 out of 10, Exceptional, (2)
"Condo is very clean and has a well stocked kitchen, and the property has lots of nice amenities. Perfect location that’s essentially ski in ski out. Loved our stay and can’t wait to come back. "
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
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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Other property types in Western Massachusetts

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1803)
"The property was clean and the staff very accommodated."
The price is AED 418
AED 507 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
5 May - 6 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.

Frequently asked questions

How much do condos in Western Massachusetts cost?
Condos in Western Massachusetts range from AED 327 to AED 551 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 43 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.