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Compare 46 Condo Rentals in Cheshire with updated reviews, rates, and availability.

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, (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
Exterior
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
Beach
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
Fridge, microwave, stovetop, dishwasher
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!
Exterior
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.
2 bedrooms, iron/ironing board, WiFi, bed sheets
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.
Exterior
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
Snow and ski sports
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
Exterior
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
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, (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
Pool
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Interior
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
10.0 out of 10, Exceptional, (9)
"Love the ski in and out of this property. Family enjoyed staying here, highly recommended."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Fridge, microwave, oven, stovetop
Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
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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 Cheshire

Exterior
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 $154
$169 total
includes taxes & fees
May 30 - May 31
Jiminy Peak Mountain Resort
Fridge, microwave, oven, stovetop
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
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
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.

Cheshire Condo Rentals information

Number of reviews
145
Accommodation
46 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

How much do condos in Cheshire cost?
The price range for condos in Cheshire is to per night. Whatever your budget, you’re sure to find someplace that suits your needs — as well as your whole crew! 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 Cheshire?
Cheshire has 46 condos. To help you find a place that’s right for you, use our filters to search for the perks or amenities you need.
Are there any family-friendly condos in Cheshire?
Take the troops to Vacation Village In The Berkshires and make your stay in Cheshire a memorable one. This family-friendly condo has a 3-star rating and amenities such as assistive listening devices and a 24-hour front desk. Once you’ve checked in and dropped off your things, there’s no shortage of family-friendly attractions to explore in and around Cheshire. Jiminy Peak Mountain Resort and Mount Greylock guarantee a good time for young and old.
Why book your condo in Cheshire with Expedia?
Expedia makes it a cinch to find your dream condo in Cheshire. After a luxury stay? Make the most of our filters to search for properties with a 5-star rating. If you have a budget, choose how much you’d like to spend and then browse our incredible deals. We’ll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap condos in Cheshire?
The simplest way to uncover cheap condos in Cheshire is with Expedia’s user-friendly filter tool. Narrow your search results by budget, star rating and amenities to discover unbeatable bargains in just a few clicks.
What is there to do in Cheshire near my condo?
Cheshire has enough activities and experiences to keep you amused for weeks, beginning with Jiminy Peak Mountain Resort. Pittsfield State Forest, Berkshire Museum and Williamstown Theatre Festival are other well-known attractions. If you’re lingering longer, Colonial Theater and Barrington Stage Company will put the finishing touches on your itinerary.

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