Title: Top Winchester Cabin Rentals | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cabins in Winchester for Rent from CA $990 - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&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 three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&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) ## Our top choices for Winchester cabin rentals ![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse Cabin vacation rentals in Berkshire County [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) Sheffield 10/10 Exceptional (9) "Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) deborah d. CA $568 CA $990 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/0a7211f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/40085f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/27f61679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/115000000/114850000/114848300/114848278/98e690c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Cabin with Sauna, Hot Tub & Cold Plunge [](https://www.expedia.ca/Cornwall-Bridge-Hotels-Cozy-Cabin-On-5-Acres-W-Hot-Tub-Fire-Pit.h114848278.Hotel-Information) Cornwall 10/10 Exceptional (5) "This cabin is so cute we had a relaxing time , will return" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candice S. [](https://www.expedia.ca/Cornwall-Bridge-Hotels-Cozy-Cabin-On-5-Acres-W-Hot-Tub-Fire-Pit.h114848278.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=2025-12-24&endDate=2025-12-25®ionId=553248635975869849&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FWinchester-Cabins.d553248635975869849-aaCabins.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cabins.d553248635975869849-aaCabins.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Clean room, staff were friendly, helpful and kind. Quiet even with planes landing right next door. Can't compliment this place enough." [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "Great customer service!" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Simsbury Inn](https://images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8_y.jpg) ### Simsbury Inn 10/10 Excellent "The personnel was very helpful & accomodating, both at the front desk & upstairs restaurant. I appreciated that they set out two rooms as adjoining even before I asked. " [](https://expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.Hotel-Information) ![DoubleTree by Hilton Hotel Bristol, Connecticut](https://images.trvl-media.com/lodging/1000000/10000/5300/5265/7a34507b_y.jpg) ### DoubleTree by Hilton Hotel Bristol, Connecticut 10/10 Excellent "Every thing exceeded expectations" [](https://expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hotel-Bristol.h5265.Hotel-Information) ![Homewood Suites by Hilton Hartford-Farmington](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/4f26a2b3_y.jpg) ### Homewood Suites by Hilton Hartford-Farmington 10/10 Excellent "Friendly staff, quick check in. Room is quiet and clean." [](https://expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information) ![Home2 Suites by Hilton Bristol](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00_y.jpg) ### Home2 Suites by Hilton Bristol 10/10 Excellent "spotless" [](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Yes" [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](https://images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Clean " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Days Inn by Wyndham Torrington](https://images.trvl-media.com/lodging/1000000/50000/50000/49932/c8b8e6a2_y.jpg) ### Days Inn by Wyndham Torrington 10/10 Excellent "Clean comfortable room,great parking and local shopping " [](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ## Find out more about Winchester ## Winchester Cabin Rentals information | Number of reviews | 14 | | ----------------- | ---------------- | | Accommodation | 12 Cabin Rentals | | Lowest Price | CA $990 | | Highest Price | CA $990 | ## Frequently asked questions ### What are the best cabins near Winchester? ### Are there cheap cabins near Winchester? ### What are the best mountain cabins near Winchester? ### What are the best river cabins near Winchester? ### What are the best cabins with pools near Winchester? ### Can I find beach cabins near Winchester? ### What are the best weekend cabin rentals in Winchester? ### What are the best cabin prices near Winchester? ### Can I find log cabins in Winchester? ### What are the highest-rated cabins in Winchester? ### Why should I book a cabin in Winchester? ### What are the top nature cabins in Winchester? ## Explore a world of travel with Expedia - 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