Title: Chester Condominium Resort Rental from CA $218 | Expedia.ca

 

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides)

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# Find and Compare Chester Condo Resort Rentals

## Check prices for these dates

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chester Condo Resorts

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(134)

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

michelle

CA $195

CA $218 total

includes taxes & fees

Dec 5 - Dec 6

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-03&endDate=2025-12-04&regionId=6005399&adults=2&lodging=CONDO_RESORT&sort=RECOMMENDED&openPlayBack=true)

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## Top Chester Hotel Reviews

### Homewood Suites by Hilton Hadley Amherst

10/10 Excellent

"Clean room, spacious room, nice staff, and good location for our trip. "

[](https://expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

### Quality Inn West Springfield

10/10 Excellent

"Very courteous staff. Comfortable, clean room. Always interesting people travelling through."

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Great stay!"

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

### Berkshire Mountain Lodge

10/10 Excellent

"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

### Courtyard by Marriott West Springfield

10/10 Excellent

"Work trip meet my needs"

[](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

### The Ellery

10/10 Excellent

"I stayed in a double queen room with my daughter on a visit to Smith. The room was very comfortable, the host was delightful l, and the breakfast was delicious! Will be back!"

[](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information)

### Quality Inn Westfield - Springfield

10/10 Excellent

"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."

[](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information)

## Find out more about Chester

## Chester Condo Resorts information

| Number of reviews | 133 |
| --- | --- |
| Accommodation | 1 Condo Resorts |
| Lowest Price | CA $218 |
| Highest Price | CA $218 |

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