Title: Chester Vacation Home Rentals from CA $293: Search Top Private Vacation Homes for Rent | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx58468)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d58468.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d58468.Travel-Guide-VacationRentals)[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) ![](https://images.trvl-media.com/place/6058263/da13667f-ebfc-4552-9481-a816443c7daf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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 three months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-05-08&endDate=2026-05-10&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 homes ![Property grounds](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/333c8891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/96000000/95160000/95159600/95159566/fc12540e.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) ![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) ### 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 reviews) "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 $160 CA $293 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Western-Shore-Hotels-Oceanfront-Luxury-Magical-Views-Sunset-And-Sunrise.h95159566.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) ![Exterior](https://images.trvl-media.com/lodging/124000000/123530000/123526500/123526477/b9564cbf.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) ### Vacation Home in Bridgewater [](https://www.expedia.ca/Bridgewater-Hotels-Private-Balcony-View-Riverside-Walk-Prime-Downtown.h123526477.Hotel-Information) CA $75 CA $160 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/Bridgewater-Hotels-Private-Balcony-View-Riverside-Walk-Prime-Downtown.h123526477.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108970000/108967000/108966921/2d8a193c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108970000/108967000/108966921/4be1c587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108970000/108967000/108966921/7444772d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108970000/108967000/108966921/1d7ed732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lunenburg [](https://www.expedia.ca/Blue-Rocks-Hotels-Coastal-Gale.h108966921.Hotel-Information) 9.8/10 Exceptional (7 reviews) "This home is very comfortable & the location was convenient for us. The scenery is beautiful and we enjoyed the hot tube. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Linda G. CA $285 CA $564 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/Blue-Rocks-Hotels-Coastal-Gale.h108966921.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121900000/121898600/121898530/d511cbe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121900000/121898600/121898530/d06ca817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121900000/121898600/121898530/b2e96307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121900000/121898600/121898530/f0204ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chester [](https://www.expedia.ca/East-Chester-Hotels-Spacious-Chester-Home-With-Spectacular-Ocean-Views.h121898530.Hotel-Information) CA $350 CA $779 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/East-Chester-Hotels-Spacious-Chester-Home-With-Spectacular-Ocean-Views.h121898530.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=2026-01-30&endDate=2026-01-31®ionId=58468&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Chester%2C+Nova+Scotia%2C+Canada®ionId=58468&latLong=44.542114%2C-64.238884&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CONDO) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d58468-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d58468-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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 "The room was great as always in the downstairs Suite.The lady working the desk Saturday January 10th afternoon was above and beyond quality service. " [](https://expedia.ca/Lunenburg-Hotels-Days-Inn-Conference-Center-By-Wyndham-Bridgewater.h62699.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 "Friendly staff, great restaurant " [](https://expedia.ca/Lunenburg-Hotels-Best-Western-Plus-Bridgewater-Hotel-Convention-Centre.h3812334.Hotel-Information) ![The Dockside Inn & Restaurant](https://images.trvl-media.com/lodging/13000000/12370000/12361500/12361417/584ec414_y.jpg) ### The Dockside Inn & Restaurant 10/10 Excellent "Nice view over the dock. Simple affair but comfortable for the 1 night. " [](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) ![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) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 27 | | ----------------- | ----------------- | | Accommodation | 74 Vacation Homes | | Lowest Price | CA $293 | | Highest Price | CA $779 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [3 Star Hotels in Gold River ](https://www.expedia.ca/3Star-Gold-River-Hotels.s30-0-d553248635977184228.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Gold River ](https://www.expedia.ca/4Star-Gold-River-Hotels.s40-0-d553248635977184228.Travel-Guide-Filter-Hotels) - [Hotels near Amicus Gallery ](https://www.expedia.ca/Amicus-Gallery-Hotels.0-l6301678-0.Travel-Guide-Filter-Hotels) - [Hotels near Chester Art Center ](https://www.expedia.ca/Chester-Art-Center-Hotels.0-l6309742-0.Travel-Guide-Filter-Hotels) - [Farmstay in Chester Basin ](https://www.expedia.ca/Chester-Basin-Agritourism.d553248635975850933-aaAgritourism.Travel-Guide-Accommodation) - 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