Title: Winchester Cottages from CA $91 | 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) # Search Winchester Cottage Rentals from CA $91 - ![](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 Cottages We don't have any properties that match your exact search [See all properties in Winchester](https://expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20®ionId=3000435714&adults=2) ## Recommended hotels in Winchester ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/c30882b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/1baf1987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/fc256dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/513649eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Jacksonville Inn Jacksonville 8.4/10 Very good (733) "Nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jacob CA $105 CA $120 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/2a692595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/c41d8356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/5c8e6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites South Jacksonville Jacksonville 9.4/10 Exceptional (608) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis CA $113 CA $125 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/3b913bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/bb05caaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/c2f3b0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG Jacksonville 7.8/10 Good (432) "It was clean with friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $91 CA $101 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/dc6867b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/22fcac0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/df8698e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Jacksonville near I-72 Jacksonville 7.8/10 Good (415) "Easy check in and out very personable and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $84 CA $93 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/132a4454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/3c66858b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Jacksonville Jacksonville 8.2/10 Very good (609) "Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayla CA $80 CA $91 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/b5efafaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8fabc5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (Double Queen Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8f50dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/e9628a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### William Watson Hotel Pittsfield 9.2/10 Wonderful (344) "Small town feel, felt safe walking around at all times of the day. Was in town for a wedding and the location was perfect. AC worked great and beds were comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $114 CA $126 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/24c58aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/3cd6537f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/9192d41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Jacksonville Jacksonville 8.8/10 Excellent (487) "Great spot " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $114 CA $130 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/b4ce7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/873e4e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/47811fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites Pittsfield 9.6/10 Exceptional (57) "Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake CA $165 CA $181 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/c466d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (New building)](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/2c579c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Acres Hotel Pittsfield 8.6/10 Excellent (140) "Best room for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $209 CA $230 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/e975b6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/92a8744a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/w3837h2569x3y3-79e6a5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/b7e82af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Jacksonville Jacksonville 7.0/10 Good (847) "Clean Rooms, friendly atmosphere. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $96 CA $106 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Springfield-Hotels-Baymont-By-Wyndham-Jacksonville.h1304355.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/74c9995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/13f55165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/16c3be32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield 6.8/10 (122) "Quick easy check-in, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $88 CA $96 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/e9218eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/70af4e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/d188b5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/b9129591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knights Inn Jacksonville East Morton Ave Jacksonville 6.8/10 (163) "Great value. Nice, comfy bed, clean bedding, no-stink room. Did not expect to like this accommodation so much, but they surprised us!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $90 CA $103 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Springfield-Hotels-Knights-Inn-Jacksonville-East-Morton-Ave.h9309491.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w905h683x60y0-bbfcfe44.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) ![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) ### 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 11 - Nov 12 [](https://www.expedia.ca/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/ad1fc48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, printers](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/0e153112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/17bf5b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/ff0589d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Farmhouse Loft "Greene County's Guesthouse" Carrollton 9.8/10 Exceptional (60) "Communication was excellent, got to check in early. Love this place, cozy, will definitely stay again when visiting friends and relatives" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jo M. CA $119 CA $231 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Carrollton-Hotels-The-Farmhouse-Loft-Greene-Countys-Guesthouse.h20348849.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/0a889b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/0aadb1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/64202e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22130000/22120700/22120643/c9590e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful studio retreat surrounded by prairie, wildlife, and open skies. Murrayville 10/10 Exceptional (25) "Great spot for our weekend away!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin M. CA $121 CA $158 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Native-Prairie-Setting-Pets-Allowed.h22120643.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/64356a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/0778f0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/09335ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa DeWolf Jacksonville 10/10 Exceptional (10) "If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine [](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/w3096h4111x0y17-1e7de191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/270-0cf1fa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/b424f2b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. Murrayville 9.8/10 Exceptional (58) "Kevin is a fantastic host! A serene setting nestled in with nature!We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $107 CA $143 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/9b551050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/7adb2ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/60663cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38760000/38750700/38750608/3b40112f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS! Bluffs 10/10 Exceptional (58) "Beautiful home on the most beautiful property and the most friendly owners! We will be back to stay at this location for sure." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) morgan a. CA $252 CA $306 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Completely-Renonvated-Country-Home-With-Llamas-Just-Outside-THE-Windows.h38750608.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) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109410000/109404500/109404431/w1079h1437x0y3-bfee123b.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 7 - Nov 8 [](https://www.expedia.ca/Pittsfield-Hotels-Lakeside-Lodge-Of-LEGENDS-A-Wilderness-Wanderers-Wonderland.h109404431.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) ![Interior](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c.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) ![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 11 - Nov 12 [](https://www.expedia.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.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-Cottages.d3000435714-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Cottages.d3000435714-aaCottages.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 Cottages information | Number of reviews | 5,094 | | --- | --- | | Accommodation | 2 Cottages | | Lowest Price | CA $91 | | Highest Price | CA $495 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Alsey Hotels](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Arcadia](https://www.expedia.ca/Arcadia-Apartments.d553248635975871406-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Arenzville](https://www.expedia.ca/Arenzville-Cabins.d3000346095-aaCabins.Travel-Guide-Accommodation) - 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