Search Condo Rentals in Western Massachusetts

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Compare 42 Condo Rentals in Western Massachusetts with updated reviews, rates, and availability.

Snow and ski sports
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
10.0 out of 10, Exceptional, (21)
"I cannot say enough good things about this condo and the host! Colin was so easily reachable and even last minute we were able to add another night onto our stay. We had 2 little ones and 4 adults and we were so comfortable with all the space. Every amenity you think you may need was there, we didn’t find ourselves saying “Oh I wish there was…” one time! It was the perfect location for us while our group was there meeting in that building. The balcony views were phenomenal and if our group comes...
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Interior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.4 out of 10, Exceptional, (12)
"Justine was a great host, and was quick to respond to all my texts. The condo was clean equipped with the basic amenities. He provided us with a drip coffee machine, but you could also get complimentary Keurig coffee every morning from the lobby. The only small inconvenience to our stay was that there was no heat in the living room, and although there is a vent from the bedroom into the living room, it didn't seem to circulate the warm air from the bedroom into the living room. The front desk...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
10.0 out of 10, Exceptional, (6)
"The property was as advertised. Clean and comfortable. And right on the mountain - ski-in/ski-out. Perfect for families."
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
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Exterior
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
9.8 out of 10, Exceptional, (9)
"The unit was clean and was accurately described on the listing. Check in was easy. This was our second time here and will return again."
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
10.0 out of 10, Exceptional, (5)
"We love Bentley Brook! We will come back next year!"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Interior detail
Welcome to Honey Spot!
10.0 out of 10, Exceptional, (24)
"We loved this property! Had everything we needed and we didn't have time to use or enjoy everything. The beds were SO COMFY!!! Loved having 2 bathrooms also. Great communication with the host! We would love to come back!"
The price is AED 496
AED 1,096 total
includes taxes & fees
27 May - 28 May
Welcome to Honey Spot!
Interior
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
5.4 out of 10, (3)
"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 441
AED 1,138 total
includes taxes & fees
10 Jun - 11 Jun
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.
Snow and ski sports
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, (33)
"We loved our stay at this beautiful condo. Clean and perfectly suited at the base of Jiminy Peak. Host was responsive and provided excellent detailed instructions."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Property grounds
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!
Charlemont Vacation Rental | 3BR | 1.5BA | 1,800 Sq Ft | 2 Steps to Enter
Berkshires Getaway < 1 Mi Skiing & Hiking!
10.0 out of 10, Exceptional, (10)
"Beautiful spot, great location right at the mountain! We had such a great time here!"
Berkshires Getaway < 1 Mi Skiing & Hiking!
Room
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (8)
"Very comfortable and convenient space. It easily accommodated me and my two teenaged children. The proximity to the ski lifts at Jiminy Peak is a great feature."
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Room
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
4.0 out of 10, (1)
"Listing is inaccurate. Clearly said 2 bedrooms in ad., but it is only 1."
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Snow and ski sports
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
9.6 out of 10, Exceptional, (7)
"Everything was perfect for a ski weekend"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Property grounds
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
9.6 out of 10, Exceptional, (5)
"Perfect stay at Jiminy Peak. Unit had everything I needed."
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo
10.0 out of 10, Exceptional, (6)
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Snow and ski sports
Outside Adventure-Skiing, Hiking, and Relaxation
10.0 out of 10, Exceptional, (1)
"Weather didn't help but the rental and the location were exceptional!"
Outside Adventure-Skiing, Hiking, and Relaxation
Property grounds
Ski on ski off 1 Br loft condo in the village center with private gated parking
10.0 out of 10, Exceptional, (13)
"My friends and I were looking for a close escape from Albany, NY. When we entered the condo we immediately felt a sense of ease and once the wood burning fire was started we were in heaven. The condo is in the perfect location within the JP Village. We were able to walk to the Country Store, Bars and Restaurants. What was PERFECT was the close proximity to the lifts; right out the door. We could ski on, ski off and take breaks without dealing with the crowds in the food halls. The condo itself...
Ski on ski off 1 Br loft condo in the village center with private gated parking
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
10.0 out of 10, Exceptional, (1)
"We very much enjoyed our stay. The place was very comfortable and very clean. The location worked out perfect and the parking was very convenient."
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
10.0 out of 10, Exceptional, (1)
"great stay as always!"
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
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See all available properties in Western Massachusetts
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.

Other property types in Western Massachusetts

Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is AED 584
AED 641 total
includes taxes & fees
27 May - 28 May
Jiminy Peak Mountain Resort
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
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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