Title: Chester Vacation Rentals from CA $245: 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 which includes a bay or harbour, a coastal town and sailing](https://images.trvl-media.com/place/58468/f34c9d07-bf50-4f98-b6b0-f47258794d90.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/58468/f34c9d07-bf50-4f98-b6b0-f47258794d90.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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=58468&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 four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=58468&startDate=2026-05-15&endDate=2026-05-17&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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/114000000/113580000/113577500/113577477/2ca590c6.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) ### Black Forest Cabins [](https://www.expedia.ca/Mahone-Bay-Hotels-Black-Forest-Cabins.h113577477.Hotel-Information) Mahone Bay 10/10 Exceptional (22 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 $185 CA $245 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, 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, 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) ### Oakhill Pines Campground [](https://www.expedia.ca/Oakhill-Hotels-Oakhill-Pines-Campground.h108813648.Hotel-Information) Oak Hill 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 $112 CA $128 total includes taxes & fees Jan 24 - Jan 25 [](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=2026-02-06&endDate=2026-02-07®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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CHALET) 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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=CONDO) 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=2026-04-22&d1=2026-04-22&endDate=2026-04-25&d2=2026-04-25&lodging=VILLA) ![](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-Vacation-Rentals.d58468.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Vacation-Rentals.d58468.Travel-Guide-VacationRentals) ## 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) ![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. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Chester ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [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) - [Farmstay in Chester ](https://expedia.ca/Chester-Agritourism.d58468-aaAgritourism.Travel-Guide-Accommodation) - [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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