Title: Chester Condo Rentals | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/5376b74ed08fb0cd0348035ae5ca74c9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Elizabeth Massa Peroulakis # Search Condos Rentals in Chester ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Condo Rentals ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/22f66f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/dd2937db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/f9dd0939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/ab36cb2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Lakeside Escape in the Berkshires Lenox 10/10 Exceptional (1) "perfect location to go everywhere in the Berkshires" [](https://www.expedia.ca/Lenox-Hotels-Tranquil-Lakeside-Escape-In-The-Berkshires.h116593874.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/dba923f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/e0957bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/3996a0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/25c39568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 1BR Condo with Pond View Lenox 8.0/10 Very good (2) "Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing." [](https://www.expedia.ca/Lenox-Hotels-Peaceful-1BR-Condo-With-Pond-View.h116593867.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39940000/39935000/39934975/dc44e881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/40000000/39940000/39935000/39934975/218703a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39935000/39934975/3cee160d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39940000/39935000/39934975/f6947bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College! Northampton 10/10 Exceptional (1) "I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!" [](https://www.expedia.ca/Northampton-Hotels-Rest-In-The-Noho-Nest.h39934975.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75190300/75190291/99190437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75190300/75190291/a7b5bdcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/76000000/75200000/75190300/75190291/31e48073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75200000/75190300/75190291/62de5616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect for Winter Skiing!! Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Vacation-Condo-Extraordinaire.h75190291.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31950000/31948900/31948898/7efeafa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31950000/31948900/31948898/331001dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31950000/31948900/31948898/9c0ed814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/32000000/31950000/31948900/31948898/abcb80b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood Lee 10/10 Exceptional (2) "It is located near everything" [](https://www.expedia.ca/Lenox-Hotels-Elegant-4-BR-Condo-In-Lenox.h31948898.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116190000/116185300/116185237/3469f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116190000/116185300/116185237/767ae9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116190000/116185300/116185237/037a31d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116190000/116185300/116185237/b7f20f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025 Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Thanksgiving-In-Pittsfield.h116185237.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48200000/48192600/48192585/c7c4de59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48200000/48192600/48192585/w1401h1859x31y20-979ac2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48200000/48192600/48192585/8d75d81d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48200000/48192600/48192585/6a438f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A cozy rest in tiny home of a nest (downtown Northampton) Northampton [](https://www.expedia.ca/Northampton-Hotels-A-Cozy-Rest-In-Tiny-Home-Of-A-Nest.h48192585.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/117000000/116500000/116497800/116497740/28904ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116500000/116497800/116497740/382fd053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/117000000/116500000/116497800/116497740/845b71cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116500000/116497800/116497740/26a07b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer in the Berkshires: Cozy country condo in charming Stockbridge MA. Lee [](https://www.expedia.ca/Stockbridge-Hotels-Summer-In-The-Berkshires-Cozy-Country-Condo-In-Charming-Stockbridge-MA.h116497740.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91230000/91220400/91220307/96846f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91230000/91220400/91220307/4597f040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91230000/91220400/91220307/04515c27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/92000000/91230000/91220400/91220307/0a2d47c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Condo with resort amenities Lenox [](https://www.expedia.ca/Lenox-Hotels-Cozy-Condo-With-Resort-Amenities.h91220307.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92960000/92957500/92957458/40dc8aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92960000/92957500/92957458/w1440h954x0y8-6d60d153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/93000000/92960000/92957500/92957458/faa124cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, stereo, offices](https://images.trvl-media.com/lodging/93000000/92960000/92957500/92957458/705139e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo with Resort Amenities in Lenox Lenox [](https://www.expedia.ca/Lenox-Hotels-Condo-With-Resort-Amenities-In-Lenox.h92957458.Hotel-Information) ![Dishwasher](https://images.trvl-media.com/lodging/93000000/92900000/92897700/92897615/71db2cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92897700/92897615/4e979a30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92897700/92897615/0eec9dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92900000/92897700/92897615/825bea2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Condo, walk to town, private and bright Lenox [](https://www.expedia.ca/Lenox-Hotels-Cozy-Condo.h92897615.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=2025-10-17&endDate=2025-10-18®ionId=6005399&adults=2&lodging=CONDO&sort=RECOMMENDED&openPlayBack=true) ![](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.d6005399-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Condos.d6005399-aaCondos.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great place! Food excellent ss well!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Tru by Hilton Chicopee Springfield](//images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Pleasant stay" [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Quality Inn West Springfield](//images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg) ### Quality Inn West Springfield 10/10 Excellent "Clean place " [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Hotel is nice and rooms are nice. They could use some updating of the furniture in the room I stayed at but overall a nice place with a nice breakfast included " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Quality Inn Chicopee - Springfield](//images.trvl-media.com/lodging/1000000/860000/856300/856259/4454c273_y.jpg) ### Quality Inn Chicopee - Springfield 10/10 Excellent "The staff was very friendly and professional. Rooms are very clean and quiet. Will definitely stay again." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](//images.trvl-media.com/lodging/1000000/20000/15800/15705/43807f20_y.jpg) ### Baldwin Inn & Suites, SureStay Collection by Best Western 10/10 Excellent "We stayed here when we went to an event at the eastern states exposition. It was coles, by so we were able to walk from the hotel to the fairgrounds" [](https://expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Courtyard by Marriott West Springfield](//images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "Ryan at front desk was friendly and courteous over the phone and upon arrival! " [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ![The Ellery](//images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 10/10 Excellent "Great stay" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Chester ## Chester Condo Rentals information | Number of reviews | 2 | | --- | --- | | Accommodation | 11 Condo Rentals | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [B&B in Becket](https://www.expedia.ca/Becket-Bed-And-Breakfast.d6005395-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Becket](https://www.expedia.ca/Becket-Chalets.d6005395-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Becket](https://www.expedia.ca/Becket-Guest-Houses.d6005395-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Cheap-Hotels.0-0-d6005395-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Luxury-Hotel.0-0-d6005395-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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