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Compare 46 Condo Rentals in Cheshire with updated reviews, rates, and availability.
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 2
10.0 out of 10, Exceptional, (21)
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.4 out of 10, Exceptional, (12)
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
10.0 out of 10, Exceptional, (6)
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Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
9.8 out of 10, Exceptional, (9)
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
10.0 out of 10, Exceptional, (5)
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, (33)
Berkshires Getaway < 1 Mi Skiing & Hiking!
Berkshires Getaway < 1 Mi Skiing & Hiking!
10.0 out of 10, Exceptional, (10)
UNIQUE - 1BR Country Condo @ Jiminy Peak
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (8)
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
4.0 out of 10, (1)
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
9.6 out of 10, Exceptional, (7)
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
9.6 out of 10, Exceptional, (5)
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Ski In & Ski Out - Deluxe 1 Bedroom Condo
10.0 out of 10, Exceptional, (6)
Outside Adventure-Skiing, Hiking, and Relaxation
Outside Adventure-Skiing, Hiking, and Relaxation
10.0 out of 10, Exceptional, (1)
Ski on ski off 1 Br loft condo in the village center with private gated parking
Ski on ski off 1 Br loft condo in the village center with private gated parking
10.0 out of 10, Exceptional, (13)
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
10.0 out of 10, Exceptional, (1)
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
10.0 out of 10, Exceptional, (1)
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
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, (9)
Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
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
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (857)
The price is $154
$169 total
includes taxes & fees
May 30 - May 31
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
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
Recent reviews of Cheshire hotelsExpedia verified reviews
5/5 Excellent
"Only issue we had was some weird brown foam in the hot tub and the construction crew working in the unit above us."
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 10 hours ago
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