Title: Chester Cottages from CA $756 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester cottages

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/708e6bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/c1c12e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/539e07bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/bee0b9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 12-acre Vacation Rental in the Berkshires!

[](https://www.expedia.ca/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

Charlemont

CA $337

CA $756 total

includes taxes & fees

Apr 3 - Apr 4

[](https://www.expedia.ca/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.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.

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## Find vacation rentals that suit your style

Aparthotels

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Cabins

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Apartments

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Villas

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Condos

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Cottages

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Private vacation homes

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## Top Chester Hotel Reviews

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

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

8/10 Good

"Room temperature was good. Breakfast coukd improve, lack of protein, muffins were not fresh. "

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then"

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Fairfield Inn & Suites Springfield Holyoke](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048_y.jpg)

### Fairfield Inn & Suites Springfield Holyoke

8/10 Good

"The staff at check in was the least professional I have ever encountered. "

[](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/f05f40a5_y.jpg)

### La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good

"Staff was nice. The foid was only so so, but it is usually that way with this type of hotel "

[](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information)

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"staff was friendly and breakfast was ok"

[](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight."

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

![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg)

### Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"Brava, to all the staff here"

[](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information)

![Candlewood Suites West Springfield by IHG](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/537cea4c_y.jpg)

### Candlewood Suites West Springfield by IHG

8/10 Good

"."

[](https://expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.Hotel-Information)

![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4_y.jpg)

### Tru by Hilton Chicopee Springfield

10/10 Excellent

"Good hotel! Would stay here again!"

[](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information)

## Find out more about Chester

## Chester Cottages information

| Number of reviews |             |
| ----------------- | ----------- |
| Accommodation     | 78 Cottages |
| Lowest Price      | CA $756     |
| Highest Price     | CA $756     |

## Frequently asked questions

### Why book your cottage in Chester with Expedia?

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### What is there to do in Chester near my cottage?

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