Photo by Ed Gaffny

Search Condos Rentals in Cheshire from CA $113

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Browse Select Cheshire Condo Rentals

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is CA $166
CA $198 total
includes taxes & fees
Mar 30 - Mar 31
Vacation Village in the Berkshires

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

7.2 out of 10, Good, (5)
"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 CA $211
CA $490 total
includes taxes & fees
Mar 30 - Mar 31
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

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 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

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (11)
"We had a great time staying at this unit. Great location on the mountain and very helpful owner. I left something in the room and Shana went out of her way to get it back to me. Thank you!"
The price is CA $113
CA $404 total
includes taxes & fees
Mar 23 - Mar 24
UNIQUE - 1BR Country Condo @ Jiminy Peak

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom

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

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

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!

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

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 Sleeps 5

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

10.0 out of 10, Exceptional, (30)
"Everything was spot on. Will be back!!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

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

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

9.4 out of 10, Exceptional, (21)
"Our stay at the Country Inn was perfect for what it was...a short weekend stay to ski for a couple days. The Inn itself is antiquated as are the rooms but the convenience of the ski-in-ski-out location was great. The room was small but adequate since we spent little time there. However, the ability to cook a couple meals there saves some bucks and was perfect. The room, and Inn, itself, could benefit from some new new furniture and decorating, but was as anticipated. Dinner on property was...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (12)
"Location was perfect! Home is cozy and well equipped! Perfect getaway for our family with great hospitality."
Berkshires Getaway < 1 Mi Skiing & Hiking!

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

10.0 out of 10, Exceptional, (2)
"This unit was absolutely perfect for our family of 4! My husband and I do not ski, but our two boys are 10 and 11 and they LOVE to ski. I enjoyed hanging inside while they went up and down the mountain. We could see them as they went by and they would wave at us. This unit was clean and it suited our needs. Staying on property is such a game changer. The kids can come in for meals and get back out of the slopes. We would definitely stay at this unit again!"
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

JIMINY PEAK - 2/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN/SKI OUT, 2BR DELUX UNIT

JIMINY PEAK - 2/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN/SKI OUT, 2BR DELUX UNIT

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

8.8 out of 10, Excellent, (3)
"The Wyndham location can't be beat for access to the mountain, especially with kids (it's literally ski in/out with the kids mountain). Good communication with a very attentive owner throughout the process. He mentioned that it will be renovated this year. Good experience overall. "
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

10.0 out of 10, Exceptional, (5)
"2-bedroom was perfect for our family of four. Great to have a kitchen, shower and tub, washer/dryer, as well as nice shampoo, conditioner, body wash, lotion, and towels for the pool. We enjoyed being so close to the mountain for skiing. JJ’s Lodge had good offerings for lunch and drinks. We also had fun at the indoor/outdoor pool and jacuzzis. Our kids have enjoyed the game room in the past but during this stay the machine to get a card loaded with money wasn’t working. They called immediately...
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

10.0 out of 10, Exceptional, (13)
"Always perfect!"
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
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 Cheshire

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"Amazing property, very clean- "
19th c. Barn in the Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is CA $166
CA $198 total
includes taxes & fees
Mar 30 - Mar 31
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is CA $213
CA $234 total
includes taxes & fees
Apr 2 - Apr 3
Jiminy Peak Mountain Resort
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 Cheshire cost?
Condos in Cheshire range from CA $113 to CA $211 per night. This will give you loads of room for your whole crew at a price that fits your 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 Cheshire?
There are 57 condos in Cheshire. Whether you’re taking a trip with the little ones or organizing a weekend break with some friends, Expedia will help you find the perfect space for your squad.
Are there any family-friendly condos in Cheshire?
If you’re planning a visit to Cheshire and need a family-friendly condo, look no further than Vacation Village In The Berkshires. This 3-star property has a fireplace and a garden. Once your vacation digs are in order, get out and check out Cheshire’s top family attractions. St Mary’s of the Assumption Church is a good place to kick off your sightseeing.
Why book your condo in Cheshire with Expedia?
We think that vacations should be stress-free, so if you’re seeking condos at a competitive rate, Expedia can help. Keep the budget under control and choose something small and affordable, or book a 5-star condo and spoil the ones you love most. Use our convenient search filters to find a stay in Cheshire that matches your needs.
How can I find cheap condos in Cheshire?
Expedia can help you easily source cheap condos in Cheshire. To discover your perfect stay in just a few keystrokes, simply use our convenient filter tool to refine your search results by star rating, budget and amenities.
What is there to do in Cheshire near my condo?
The most useful travel accessory is a well-planned to-do list. St Mary’s of the Assumption Church is a wonderful place to kick off your adventures in Cheshire.