Title: Chester Vacation Rentals from CA $172: 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 house](https://images.trvl-media.com/place/58468/ae62d7a2-f8e6-4348-8192-cdb53216bfba.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Chester Vacation Rentals

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## Check prices for these dates

Tonight

[Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-01-06&endDate=2026-01-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-01-07&endDate=2026-01-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-01-16&endDate=2026-01-18&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)

![Interior](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/d4faefb2.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)

### Cabin in Mahone Bay

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

10/10

Exceptional

(22)

"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

Feb 1 - Feb 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, 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, 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/109000000/108820000/108813700/108813648/5c3a9a09.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)

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

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

Andrea

CA $112

CA $128 total

includes taxes & fees

Jan 7 - Jan 8

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

![Property grounds](https://images.trvl-media.com/lodging/100000000/99840000/99830200/99830165/01e9c8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/100000000/99840000/99830200/99830165/98eb122a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sauna](https://images.trvl-media.com/lodging/100000000/99840000/99830200/99830165/3b2518b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99840000/99830200/99830165/3dd59e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Boutiliers Point

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C6.h99830165.Hotel-Information)

10/10

Exceptional

(9)

"The cabin was very private and it was nice having the hot tub on our front deck."

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

Jane T.

CA $129

CA $183 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C6.h99830165.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/116000000/115660000/115659400/115659336/8307e4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/116000000/115660000/115659400/115659336/ce75d283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/116000000/115660000/115659400/115659336/bc3d752b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115660000/115659400/115659336/0349881e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Windsor Road

[](https://www.expedia.ca/Windsor-Road-Hotels-Tiny-Home-In-Chester-Nova-Scotia-Hosted-By-Dordean-Suites.h115659336.Hotel-Information)

10/10

Exceptional

(7)

"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"

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

Carol

CA $149

CA $202 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Windsor-Road-Hotels-Tiny-Home-In-Chester-Nova-Scotia-Hosted-By-Dordean-Suites.h115659336.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92630000/92621600/92621568/6ae3472d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92630000/92621600/92621568/449a1be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92630000/92621600/92621568/53e57031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92630000/92621600/92621568/w4007h1959x5y0-347ce71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lunenburg

[](https://www.expedia.ca/Front-Centre-Hotels-Beautiful-Home-On-Sunny-Acreage-Wfull-Bath-Nearby-Ocean.h92621568.Hotel-Information)

9.6/10

Exceptional

(9)

"We enjoyed our stay very much! "

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

Kimberley K.

CA $179

CA $272 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Front-Centre-Hotels-Beautiful-Home-On-Sunny-Acreage-Wfull-Bath-Nearby-Ocean.h92621568.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/100000000/99830000/99826900/99826887/2cac8a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99830000/99826900/99826887/79748a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/100000000/99830000/99826900/99826887/f69c1cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99830000/99826900/99826887/e31747f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Chester Basin

[](https://www.expedia.ca/Windsor-Road-Hotels-Tiny-Home-In-Chester-Nova-Scotia-Hosted-By-Dordean-Suites.h99826887.Hotel-Information)

9.8/10

Exceptional

(14)

"There’s so much about Dordéan Suites to like: a contemporary, fun alternative to large, impersonal corporate roadside hotel. Loved our place, loved our stay! "

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

Karil

CA $149

CA $202 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Windsor-Road-Hotels-Tiny-Home-In-Chester-Nova-Scotia-Hosted-By-Dordean-Suites.h99826887.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526480/191bb33c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526480/499fe487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526480/d6eaddbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526480/364daef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Hot-Choco-Bar-Backyard-Access-Private-Entry.h123526480.Hotel-Information)

10/10

Exceptional

(1)

"Perfect place to stay. We will be back for sure."

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

Geoff M.

CA $108

CA $180 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Bridgewater-Hotels-Hot-Choco-Bar-Backyard-Access-Private-Entry.h123526480.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131432/ef6428c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131432/edd24d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131432/c7361007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131500/119131432/3be87ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lunenburg

[](https://www.expedia.ca/Lunenburg-Hotels-Sailboat-Suite-Heart-Of-Lunenburg.h119131432.Hotel-Information)

8.8/10

Excellent

(3)

"Good and quiet location. Not properly cleaned (pictures attached)."

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

Anonymous traveller

CA $119

CA $253 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Lunenburg-Hotels-Sailboat-Suite-Heart-Of-Lunenburg.h119131432.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110610000/110604800/110604710/a87d0a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110610000/110604800/110604710/a6304ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110610000/110604800/110604710/0caa2aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110610000/110604800/110604710/003c7d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lunenburg

[](https://www.expedia.ca/Lunenburg-Hotels-Relaxing-King-Bed-Suite-Close-To-Lunenburg-Harbour.h110604710.Hotel-Information)

10/10

Exceptional

(3)

"It is a lovely place to stay! Very clean, very inviting."

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

Danette R.

CA $130

CA $254 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Lunenburg-Hotels-Relaxing-King-Bed-Suite-Close-To-Lunenburg-Harbour.h110604710.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/333c8891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/02038258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/642333bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/2742d82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Western Shore

[](https://www.expedia.ca/Western-Shore-Hotels-Oceanfront-Luxury-Magical-Views-Sunset-And-Sunrise.h95159566.Hotel-Information)

9.6/10

Exceptional

(20)

"Excellent unit and very clean.The view was awesome.Highly recommended for a wonderful place to stay."

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

John S.

CA $175

CA $314 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Western-Shore-Hotels-Oceanfront-Luxury-Magical-Views-Sunset-And-Sunrise.h95159566.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/97000000/96990000/96981000/96980929/06187bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96990000/96981000/96980929/85b3b61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96990000/96981000/96980929/502b12d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96990000/96981000/96980929/5e86387e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Welcome-To-Our-Cozycharming-2-Bedroom-1-Bath-Apartment-In-Central-Bridgewater.h96980929.Hotel-Information)

9.4/10

Exceptional

(3)

"As described and in a great location!"

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

Erin E.

CA $190

CA $361 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Bridgewater-Hotels-Welcome-To-Our-Cozycharming-2-Bedroom-1-Bath-Apartment-In-Central-Bridgewater.h96980929.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95850000/95843500/95843426/a5a74d20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95850000/95843500/95843426/0939d88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/96000000/95850000/95843500/95843426/5f00ae13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/96000000/95850000/95843500/95843426/1cb9eb31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Chester

[](https://www.expedia.ca/Sherwood-Hotels-Indulge-In-Luxurious-Bliss-Private-Hot-Tub.h95843426.Hotel-Information)

9.0/10

Wonderful

(2)

"It was the perfect get away for myself after a rough week at work! Highly recommend. "

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

Michelle L.

CA $279

CA $364 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Sherwood-Hotels-Indulge-In-Luxurious-Bliss-Private-Hot-Tub.h95843426.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201114/90cc6f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201114/60e186b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201114/a9372da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201114/d9226c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in LaHave

[](https://www.expedia.ca/Dublin-Shore-Hotels-The-Lookout-Dome-Two-Private-Hot-Tub.h118201114.Hotel-Information)

9.8/10

Exceptional

(10)

"Unique property with a great view of the ocean. Great location for exploring the surrounding towns and coastline."

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

Gary D.

CA $315

CA $518 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Dublin-Shore-Hotels-The-Lookout-Dome-Two-Private-Hot-Tub.h118201114.Hotel-Information)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526477/f26b2dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526477/e0d39174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526477/cbe2cff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526477/b9564cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Private-Balcony-View-Riverside-Walk-Prime-Downtown.h123526477.Hotel-Information)

CA $90

CA $176 total

includes taxes & fees

Jan 8 - Jan 9

[](https://www.expedia.ca/Bridgewater-Hotels-Private-Balcony-View-Riverside-Walk-Prime-Downtown.h123526477.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/114000000/113450000/113446100/113446072/f91d9a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113450000/113446100/113446072/6c7f55db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113450000/113446100/113446072/0088f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113450000/113446100/113446072/5ce26ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Luxurious-2-Bedroom-With-King-And-Queen-Bed-And-15-Bathroom-Sleeps-6.h113446072.Hotel-Information)

8.8/10

Excellent

(3)

"Everything was clean. We'll set up Would stay again for sure"

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

Porter F.

CA $180

CA $361 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Bridgewater-Hotels-Luxurious-2-Bedroom-With-King-And-Queen-Bed-And-15-Bathroom-Sleeps-6.h113446072.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201108/4773f67f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201108/809fd0d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201108/5544971b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118210000/118201200/118201108/2ef422e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in LaHave

[](https://www.expedia.ca/LaHave-Hotels-The-Lookout-Dome-One-Private-Hot-Tub.h118201108.Hotel-Information)

10/10

Exceptional

(20)

"Beautiful stay. "

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

Kyle M.

CA $315

CA $518 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/LaHave-Hotels-The-Lookout-Dome-One-Private-Hot-Tub.h118201108.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99360000/99356600/99356585/w905h683x60y0-ab0c9189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99360000/99356600/99356585/w507h683x259y0-4cf6f902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99356600/99356585/w506h683x259y0-409b4a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99360000/99356600/99356585/w905h683x60y0-074d4849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bridgewater

[](https://www.expedia.ca/Bridgewater-Hotels-Abigaels-Apt-Suite-1-BR-2-BED-In-Bridgewater.h99356585.Hotel-Information)

9.0/10

Wonderful

(2)

"Nice to have all the appliances and be able to do our laundry. Good location, Wilma was a responsive host. They need better signage - the building has a barber shop in it and 3 people coming for a haircut ended up knocking on our door because they couldn't find the entrance, which is through the Bubble Tea shop. Noisy in the day time but okay for sleeping."

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

Jeannie T.

CA $162

CA $284 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Bridgewater-Hotels-Abigaels-Apt-Suite-1-BR-2-BED-In-Bridgewater.h99356585.Hotel-Information)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/118000000/117230000/117223300/117223274/w1096h878x0y827-bd704175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117230000/117223300/117223274/2a8c51b4_edited_3ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117230000/117223300/117223274/w1170h880x0y826-9f62b2c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117230000/117223300/117223274/w1170h1857x0y655-4230005f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lunenburg

[](https://www.expedia.ca/Pine-Grove-Hotels-Luxury-Lakefront-Dome-With-Private-Beach.h117223274.Hotel-Information)

9.8/10

Exceptional

(10)

"Perfect spot for a peaceful getaway with a great view. "

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

Alan L.

CA $275

CA $417 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Pine-Grove-Hotels-Luxury-Lakefront-Dome-With-Private-Beach.h117223274.Hotel-Information)

![Spa](https://images.trvl-media.com/lodging/100000000/99830000/99829200/99829197/3eda0429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99830000/99829200/99829197/c4d3134c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99830000/99829200/99829197/fda63fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99830000/99829200/99829197/w1016h683x8y0-75409ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Boutiliers Point

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C4.h99829197.Hotel-Information)

10/10

Exceptional

(7)

"It was lovely really enjoyed the property.. loved hot tub and sauna!!"

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

Mark R.

CA $179

CA $242 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C4.h99829197.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99840000/99830800/99830754/52bec330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830800/99830754/1045b533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830800/99830754/a2a170a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99840000/99830800/99830754/971ef016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Boutiliers Point

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C7.h99830754.Hotel-Information)

9.6/10

Exceptional

(10)

"Accommodation was excellent, particularly the hot tub overlooking the bay. "

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

David B.

CA $179

CA $242 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Boutiliers-Point-Hotels-Wilsons-Coastal-Club-C7.h99830754.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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## 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

"The owner and staff were unbelievably personable. Mike, the owner was truly a gem. The dockside was an amazing place to stay with great water views and amazing proximity to downtown shopping. The room is extremely clean and spacious and it was such a delight. We loved eating at the restaurant as well. That was certainly a plus. Breakfast with The view and the sunrise and sunsets were incredible. Can't wait to go back again."

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

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

### The Homeport Motel

10/10 Excellent

"Very convenient location, great communication, spacious room."

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

"Cleanliness "

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

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

### Smugglers Cove Inn

10/10 Excellent

"Yes"

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

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

### Bridgewater Hotel

10/10 Excellent

"Friendly and efficient staff."

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

![Black Forest Cabins](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/2ca590c6_y.jpg)

### Black Forest Cabins

10/10 Excellent

"Spotless room"

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

![Mahone Bay Hide-Away ](https://images.trvl-media.com/lodging/36000000/35090000/35080400/35080364/f4c98cd1_y.jpg)

### Mahone Bay Hide-Away 

10/10 Excellent

"Beautiful space, tastefully decorated, well equipped and immaculately clean! We especially enjoyed the spacious kitchen which allowed us to make a meal together with our grandchildren. Pam and Dave were wonderful, going above and beyond to ensure our stay was all it could be. We feel fortunate to have discovered this little gem, and we will definitely be back!"

[](https://expedia.ca/Lunenburg-Hotels-Mahone-Bay-Hide-Away.h35080364.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

"Our stay at Miller House by the Bay was truly delightful. The moment we stepped inside the 1800s heritage home, we were struck by its character and warmth. It’s the kind of place where history feels alive, yet every corner is inviting and comfortable. Margaret is a remarkable host. She welcomed us with such kindness and genuine care that it instantly felt like we were visiting an old friend rather than checking into accommodations. Her thoughtful touches throughout our stay made all the difference. I truly enjoyed our informal chats as Margaret is a wealth of information. Evenings were especially fun as we unwound with a marble game—a simple, fun tradition that added a surprisingly charming element to our visit. We left feeling relaxed, cared for, and already talking about when we might return. A wonderful spot for anyone looking for a stay with heart and personality."

[](https://expedia.ca/Mahone-Bay-Hotels-Miller-House-By-The-Bay.h113831212.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)
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## Frequently asked questions

### Are there vacation rentals in Chester?

### What are some of the best vacation rentals in Chester?

### How many vacation rentals will I find in Chester?

### What’s there to see and do in Chester?

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

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