Title: Chester Vacation Rentals from CA $267: Short-Term Rentals for 2026 | Expedia.ca

[Chester Travel Guide](https://expedia.ca/Chester.dx58468)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d58468.Travel-Guide-Hotels)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d58468.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d58468.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d58468.Destination-Travel-Guides)

![Chester showing a small town or village and a lake or waterhole](https://images.trvl-media.com/place/6058263/da13667f-ebfc-4552-9481-a816443c7daf.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation rentals

![Premium bedding, pillowtop beds, free WiFi](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/w1498h1003x3y0-a7933fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/2ca590c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, free WiFi](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/b3c5c2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sauna](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/2e933bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Mahone Bay

[](https://www.expedia.ca/Mahone-Bay-Hotels-Black-Forest-Cabins.h113577477.Hotel-Information)

10/10

Exceptional

(23 reviews)

"Great spot for a special night out … beds were super comfortable "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Caroline

CA $204

CA $267 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Mahone-Bay-Hotels-Black-Forest-Cabins.h113577477.Hotel-Information)

![Cabin, 1 Double Bed, Shared Bathroom](https://images.trvl-media.com/lodging/109000000/108820000/108813700/108813648/c7d372b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, Multiple Beds, Private Bathroom (Public Showers)](https://images.trvl-media.com/lodging/109000000/108820000/108813700/108813648/db2a43e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, Multiple Beds, Shared Bathroom](https://images.trvl-media.com/lodging/109000000/108820000/108813700/108813648/fb865e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, 1 Double Bed, Shared Bathroom](https://images.trvl-media.com/lodging/109000000/108820000/108813700/108813648/b1715b56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Oak Hill

[](https://www.expedia.ca/Oakhill-Hotels-Oakhill-Pines-Campground.h108813648.Hotel-Information)

9.0/10

Wonderful

(16 reviews)

"Staff was super welcoming and cabin was all set for us! "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Andrea

CA $101

CA $115 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Oakhill-Hotels-Oakhill-Pines-Campground.h108813648.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=2026-03-13&endDate=2026-03-14&regionId=58468&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CHALET)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada&regionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CONDO)

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## Top Chester Hotel Reviews

![The Dockside Inn & Restaurant](https://images.trvl-media.com/lodging/13000000/12370000/12361500/12361417/584ec414_y.jpg)

### The Dockside Inn & Restaurant

10/10 Excellent

"Amazing individuals, super understanding, respectful and just overall awesome. Highly reccomend for nova scotian hospitality!"

[](https://expedia.ca/Lunenburg-Hotels-The-Dockside-Inn-Restaurant.h12361417.Hotel-Information)

![Miller House By the Bay](https://images.trvl-media.com/lodging/114000000/113840000/113831300/113831212/61799608_y.jpg)

### Miller House By the Bay

10/10 Excellent

"The owner, Margaret, was amazing. So friendly and accommodating. Her property is beautiful and very well appointed. We will definitely be back and recommend staying here. "

[](https://expedia.ca/Mahone-Bay-Hotels-Miller-House-By-The-Bay.h113831212.Hotel-Information)

![The Homeport Motel](https://images.trvl-media.com/lodging/11000000/10570000/10568700/10568662/16214d5d_y.jpg)

### The Homeport Motel

10/10 Excellent

"The room was spotless, modern and very comfortable. Very convenient location on the edge of Lunenburg, and only 15 minutes from Bridgewater. Would definitely recommend staying here!"

[](https://expedia.ca/Lunenburg-Hotels-The-Homeport-Motel.h10568662.Hotel-Information)

![Salt Shaker Deli & Inn](https://images.trvl-media.com/lodging/12000000/11720000/11716000/11715927/f29b67eb_y.jpg)

### Salt Shaker Deli & Inn

10/10 Excellent

"Lovely room with a beautiful view "

[](https://expedia.ca/Lunenburg-Hotels-Salt-Shaker-Deli-Inn.h11715927.Hotel-Information)

![Smugglers Cove Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517100/1517064/e53b71bd_y.jpg)

### Smugglers Cove Inn

10/10 Excellent

"Great old building with so much charm. Did not expect an elevator which was very much appreciated. Operators where very friendly and knowledgeable. I will stay there again and recommend to friends and family"

[](https://expedia.ca/Lunenburg-Hotels-Smugglers-Cove-Inn.h1517064.Hotel-Information)

![Best Western Plus Bridgewater Hotel & Convention Centre](https://images.trvl-media.com/lodging/4000000/3820000/3812400/3812334/c7642643_y.jpg)

### Best Western Plus Bridgewater Hotel & Convention Centre

10/10 Excellent

"The staff was friendly and accommodating. "

[](https://expedia.ca/Lunenburg-Hotels-Best-Western-Plus-Bridgewater-Hotel-Convention-Centre.h3812334.Hotel-Information)

![Bridgewater Hotel](https://images.trvl-media.com/lodging/12000000/11070000/11060500/11060456/81caac46_y.jpg)

### Bridgewater Hotel

10/10 Excellent

"Very friendly staff and very clean rooms and rest of hotel as well "

[](https://expedia.ca/Bridgewater-Hotels-Bridgewater-Hotel.h11060456.Hotel-Information)

![Days Inn & Conference Center by Wyndham Bridgewater](https://images.trvl-media.com/lodging/1000000/70000/62700/62699/e0afbee2_y.jpg)

### Days Inn & Conference Center by Wyndham Bridgewater

10/10 Excellent

"Yes"

[](https://expedia.ca/Lunenburg-Hotels-Days-Inn-Conference-Center-By-Wyndham-Bridgewater.h62699.Hotel-Information)

![Travelodge by Wyndham Bridgewater](https://images.trvl-media.com/lodging/1000000/20000/18000/17913/12a1f767_y.jpg)

### Travelodge by Wyndham Bridgewater

10/10 Excellent

"Room had all the necessities and was fresh and clean. Staff was very courteous and helpful. Enjoyed the breakfast. We plan to stay again."

[](https://expedia.ca/Lunenburg-Hotels-Comfort-Inn.h17913.Hotel-Information)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Chester ](https://expedia.ca/Chester-Private-Vacation-Homes.d58468-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.ca/Chester-Cottages.d58468-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.ca/Chester-Apartments.d58468-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.ca/Chester-Cabins.d58468-aaCabins.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.ca/Chester-Bed-And-Breakfast.d58468-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Chester ](https://expedia.ca/Chester-Chalets.d58468-aaChalets.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.ca/Chester-Motels.d58468-aaMotels.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.ca/Chester-Inns.d58468-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.ca/Chester-Guest-Houses.d58468-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d58468-aaVillas.Travel-Guide-Accommodation)
- [RV Parks in Chester ](https://expedia.ca/Chester-RV-Parks.d58468-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Chester ](https://expedia.ca/Chester-Resort-Hotels.d58468-aaResortHotels.Travel-Guide-Accommodation)
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- [Condo Rentals in Chester ](https://expedia.ca/Chester-Condos.d58468-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chester?

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### What’s a vacation rental in Chester like?

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