Title: Top Winchester Cabin Rentals | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000435714.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Cabins in Winchester for Rent from CA $177 - ![](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 Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Cabin Rentals ![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-bbfcfe44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-6bba3640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w547h683x240y0-d6fb1b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w906h683x60y0-f10f078b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL Jacksonville 10/10 Exceptional (15) "My 2nd stay! I stayed here about 6weeks prior, enroute to visit my daughter at Mizzou. It was so nice that I decided to stay again on my way to her graduation. It was perfect again! It was warm and beautiful in the morning so I even used the outdoor tub." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly W. CA $139 CA $177 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1021h680x0y0-e4ca8d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1015h683x4y0-0f291390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1014h683x5y0-7d846d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville Jacksonville 10/10 Exceptional (8) "Quiet and cozy, just what we needed! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle D. CA $181 CA $222 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/304bbf41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/9aafb100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1080h1437x0y3-5f7123c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-36d6779a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland Pittsfield CA $353 CA $495 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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=2025-11-19&endDate=2025-11-20®ionId=3000435714&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.d3000435714-aaCabins.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cabins.d3000435714-aaCabins.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sleep Inn & Suites](//images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Quite and very pleasing staff." [](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Best Western Jacksonville Inn](//images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "I booked my room in advance,however I couldn't get in until 3pm! When check-out time is 11am! I didn't like that at all." [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![William Watson Hotel](//images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg) ### William Watson Hotel 10/10 Excellent "Everything about our stay was great. We will stay here again. The parking was good, as it was in front of the building. The restaurant was excellent." [](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Super 8 by Wyndham Jacksonville](//images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg) ### Super 8 by Wyndham Jacksonville 10/10 Excellent "Good service " [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Hampton Inn Jacksonville](//images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "My stay was great! Relaxing after a full day of work. But the best part of the trip was how wonderful your staff treated me! Madison was awesome and so kind! She offered great advice on local sites, restaurants and answered my queries with great enthusiasm. I missed her on her days off! So glad she was at the front desk the day I checked in! Also, I met another lady while staying here and we are now friends! See the attached picture of all of us… " [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Quality Inn Jacksonville near I-72](//images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "Easy check in and out very personable and friendly staff" [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](//images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw." [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!](//images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/3f150da0_y.jpg) ### PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods! 10/10 Excellent "Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. " [](https://expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.Hotel-Information) ![Baymont by Wyndham Jacksonville](//images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/w3837h2569x3y3-79e6a5e0_y.jpg) ### Baymont by Wyndham Jacksonville 10/10 Excellent "Everything new and clean " [](https://expedia.ca/Springfield-Hotels-Baymont-By-Wyndham-Jacksonville.h1304355.Hotel-Information) ## Find out more about Winchester ## Winchester Cabin Rentals information | Number of reviews | 23 | | --- | --- | | Accommodation | 5 Cabin Rentals | | Lowest Price | CA $177 | | Highest Price | CA $495 | ## Frequently asked questions ### What are the best cabins near Winchester? > Ranging from small and rustic to those full of luxury and style, you have 24 cabins to take your pick of in and around Winchester. Some popular options include [Cabin - Spacious Riverfront Perch/easy Access To St. Charles Less Than 1 Hr To St. Louis](https://www.expedia.ca/Winfield-Hotels-Spacious-Riverfront-PerchEasy-Access-To-StCharles-Less-Than-1-Hr-To-St-Louis.h34085284.Hotel-Information) and [Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions](https://www.expedia.ca/Family-Friendly-And-Perfect-For-Large-Groups-And-Family-Reunions.h33492156.Hotel-Information). ### Are there cheap cabins in Winchester? > Priced from CA $177 to CA $495 per night, getting away with the family is easy and affordable. Rent one of our cheap cabins in Winchester and enjoy some outdoorsy fun without breaking your budget.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best family cabins near Winchester? > Treat your kids to an exciting escape in one of our Winchester family cabins. [Cabin - Luxurious Otter Pointe](https://www.expedia.ca/Girard-Hotels-Luxurious-Otter-Pointe.h33004397.Hotel-Information) is an excellent option. It comes with ample amenities to make you and your crew comfy, including a toaster and children's activities. Or, make some lovely new memories together at [Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions](https://www.expedia.ca/Family-Friendly-And-Perfect-For-Large-Groups-And-Family-Reunions.h33492156.Hotel-Information). Children's activities and on-site watersports are two conveniences that await you here. ### What are the best river cabins near Winchester? > If you're searching for a comfy getaway steps from the water, a Winchester river cabin is an excellent choice. Head for [Exclusive" River Cabin On Stilts](https://www.expedia.ca/House.h70415238.Hotel-Information) and let any stresses scurry away downstream. Amenities here include outdoor furniture and a firepit. Another leading riverside property is [Little Red Cabin By The Spoon River](https://www.expedia.ca/Ipava-Hotels-Little-Red-Country-Cabin-Across-From-The-Spoon-River.h66724301.Hotel-Information). It comes with outdoor furniture, a queen bed and more. ### What are the best romantic cabins near Winchester? > Whisk your sweetheart away for a few heavenly nights at one of our romantic cabin rentals near Winchester. [Cabin - Spacious Riverfront Perch/easy Access To St. Charles Less Than 1 Hr To St. Louis](https://www.expedia.ca/Winfield-Hotels-Spacious-Riverfront-PerchEasy-Access-To-StCharles-Less-Than-1-Hr-To-St-Louis.h34085284.Hotel-Information) is a popular option for starry-eyed lovebirds. Quality amenities here include a king-sized bed and a patio. Alternatively, pop open the Champagne and curl up together at [Peaceful Cozy Cabin, With Fireplace](https://www.expedia.ca/Fieldon-Hotels-Peaceful-Cozy-Cabin.h88175786.Hotel-Information). A king-sized bed and winery tours will help fan the flames of romance. ### What are some great Winchester cabins? > From plush pads with all the fancy perks to rustic retreats that won't break the bank, Expedia has cabin rentals to suit every budget and style. Spend a few days relaxing in nature at [Little Red Cabin By The Spoon River](https://www.expedia.ca/Ipava-Hotels-Little-Red-Country-Cabin-Across-From-The-Spoon-River.h66724301.Hotel-Information). Conveniences here include an electric car charging station and a fireplace. Another quality option is [Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions](https://www.expedia.ca/Family-Friendly-And-Perfect-For-Large-Groups-And-Family-Reunions.h33492156.Hotel-Information). It offers a firepit, a nearby waterfront and more. ### What are the best weekend cabin rentals in Winchester? > Nothing's as good as a weekend cabin getaway after a big week at work. Swap the office for a few days or more in the great outdoors at [Cabin - Luxurious Otter Pointe](https://www.expedia.ca/Girard-Hotels-Luxurious-Otter-Pointe.h33004397.Hotel-Information). A patio and a fireplace are some of the conveniences it comes with. Alternatively, forget all about work at [Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions](https://www.expedia.ca/Family-Friendly-And-Perfect-For-Large-Groups-And-Family-Reunions.h33492156.Hotel-Information). Spend your nights here and make use of on-site watersports and a firepit. ### What are the best cabin prices in Winchester? > If you want to save on your stay, Expedia has some great deals on Winchester cabins that won't put a dent in your budget. Like the sound of CA $177 per night? ### What are the highest-rated cabins in Winchester? > Expedia cabin travellers just keep returning to [Cabin - Family - Friendly And Perfect For Large Groups And Family Reunions](https://www.expedia.ca/Family-Friendly-And-Perfect-For-Large-Groups-And-Family-Reunions.h33492156.Hotel-Information). This outstanding option comes with a host of useful amenities including on-site watersports and a firepit. It won't take you long to understand why [Cabin - Luxurious Otter Pointe](https://www.expedia.ca/Girard-Hotels-Luxurious-Otter-Pointe.h33004397.Hotel-Information) is also popular with travellers. Conveniences such as a patio and a fireplace will help make your stay even more comfortable. ### Why should I book a cabin in Winchester? > Affordability, rustic charm, nature-filled surroundings — there are loads of great reasons to stay in a Winchester cabin. Get away from the cacophony of the city and wake up to the sweet sound of birdsong. There's ample adventure just around the corner too. Whether you're travelling with friends, family or your special someone, you'll discover the perfect rental cabin on Expedia. ### What are the top nature cabins in Winchester? > Our nature cabins in Winchester come in assorted styles, sizes and budgets, but there's one feature they all share — excellent access to the great outdoors. [Exclusive" River Cabin On Stilts](https://www.expedia.ca/House.h70415238.Hotel-Information) is a magnet for adventure seekers. Amenities such as a barbecue grill and a firepit only make it more inviting. Whether you'd rather get your feet wandering or just put them up, do it at [Little Red Cabin By The Spoon River](https://www.expedia.ca/Ipava-Hotels-Little-Red-Country-Cabin-Across-From-The-Spoon-River.h66724301.Hotel-Information). 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