Title: Top Chester Cabin Rentals | 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)

![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Chris Addams

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four 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)

## Our top choices for Chester cabin rentals

![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/1faa3753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/669a10ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

Hinsdale

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

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

Cec C.

CA $317

CA $696 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.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=2026-02-19&endDate=2026-02-20&regionId=6005399&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CHALET)

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## Top Chester Hotel Reviews

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"loved "

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg)

### Fairfield Inn & Suites Springfield Northampton/Amherst

10/10 Excellent

"Gorgeous room amazing stay"

[](https://expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being so cold out. The hotel is well maintained. The only small complaint I had was that the bathroom in our room needs to be refreshed. We have already started talking about coming back in the warmer weather to enjoy some of the outdoor activities in in the area."

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

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great clean room. Staff great. Breakfast and selection great! "

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg)

### Hotel Northampton

10/10 Excellent

"The staff were amazing and the room was perfect. "

[](https://expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Immaculately clean and friendly staff. Easy parking and great breakfast"

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

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back "

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

![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg)

### The Ellery

10/10 Excellent

"Comfortable room, great breakfast with cozy fireplace. Friendly and efficient staff. Easy parking. Walkable area amidst Smith College and fifteen minute walk to downtown Northampton attractions and restaurants. "

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

"great room . wish they had better breakfast "

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

## Find out more about Chester

## Chester Cabin Rentals information

| Number of reviews | 35               |
| ----------------- | ---------------- |
| Accommodation     | 17 Cabin Rentals |
| Lowest Price      | CA $696          |
| Highest Price     | CA $696          |

## Frequently asked questions

### What are the best cabins near Chester?

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### What are the best mountain cabins near Chester?

### What are the best river cabins near Chester?

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### Can I find beach cabins near Chester?

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### What are the top nature cabins in Chester?

### What are some of the best cabins near International Volleyball Hall of Fame in Chester?

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