Title: Chester Condo Rentals from CA $1,598 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89014&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=89014&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=89014&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=89014&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 condo rentals ![Condo, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027641/9c252c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027641/9fb66e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Pool](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027641/59f4bd5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/91000000/90030000/90027700/90027641/57a4605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo [](https://www.expedia.ca/Killington-Hotels-Sunrise-West-Glade-3br.h90027641.Hotel-Information) Killington CA $687 CA $1,598 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Killington-Hotels-Sunrise-West-Glade-3br.h90027641.Hotel-Information) ![Condo, 4 Bedrooms | Sauna](https://images.trvl-media.com/lodging/117000000/116890000/116888100/116888019/e623b5d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 4 Bedrooms | Interior](https://images.trvl-media.com/lodging/117000000/116890000/116888100/116888019/1a03909b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/117000000/116890000/116888100/116888019/8c0e87fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 4 Bedrooms | Living area](https://images.trvl-media.com/lodging/117000000/116890000/116888100/116888019/8d7648f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunrise Bear Ridge C4 4 Bedroom Condo [](https://www.expedia.ca/Killington-Hotels-Sunrise-Bear-Ridge-C4-4-Bedroom-Condo.h116888019.Hotel-Information) Killington CA $987 CA $1,997 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Killington-Hotels-Sunrise-Bear-Ridge-C4-4-Bedroom-Condo.h116888019.Hotel-Information) ![Condo, 3 Bedrooms | Marina](https://images.trvl-media.com/lodging/69000000/68900000/68893000/68892921/35347466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/69000000/68900000/68893000/68892921/w3070h2043x0y3-b0696b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/69000000/68900000/68893000/68892921/7658aedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/69000000/68900000/68893000/68892921/w4021h3019x5y0-fe1e91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Okemo Westwood Condo 3 Bedroom Condo by RedAwning [](https://www.expedia.ca/Ludlow-Hotels-Okemo-Westwood-Condo-3-Bedroom-Condo.h68892921.Hotel-Information) Ludlow CA $932 CA $2,145 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Ludlow-Hotels-Okemo-Westwood-Condo-3-Bedroom-Condo.h68892921.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=2026-02-18&endDate=2026-02-19®ionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=APART_HOTEL) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-04&d1=2026-05-04&endDate=2026-05-07&d2=2026-05-07&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-Condos.d89014-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Condos.d89014-aaCondos.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Staff was great! Used the business office which was easily accessible, location is great! " [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg) ### Bromley View Inn 10/10 Excellent "Clean room/ great breakfast" [](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Awesome stay thank you" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Long Trail House at Stratton Mountain Resort](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1_y.jpg) ### Long Trail House at Stratton Mountain Resort 10/10 Excellent "Nice place and great location!!!" [](https://expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Friendly staff, clean rooms. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg) ### The Manchester View 10/10 Excellent "The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. " [](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg) ### Big Bears Lodge 10/10 Excellent "Yes " [](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Everything was great from the room to the staff making everything as convenient as possible." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Find out more about Chester ## Chester Condo Rentals information | Number of reviews | | | ----------------- | ----------------- | | Accommodation | 494 Condo Rentals | | Lowest Price | CA $1,598 | | Highest Price | CA $2,145 | ## Frequently asked questions ### How much do condos in Chester cost? ### How many condos are there in Chester? ### Why book your condo in Chester with Expedia? ### How can I find cheap condos in Chester? ### What is there to do in Chester near my condo? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [B&B in Andover ](https://www.expedia.ca/Andover-Bed-And-Breakfast.d6023580-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Andover ](https://www.expedia.ca/Andover-Chalets.d6023580-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Andover ](https://www.expedia.ca/Andover-Country-House.d6023580-aaCountryHouse.Travel-Guide-Accommodation) - 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