Title: Book the Best Winchester Hotels with FREE WIFI in 2025 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d177515.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d177515.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d177515.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d177515.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d177515.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 Hotels with Wifi in Winchester, TN from CA $162 ![](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 availability on Winchester Hotels with Wifi Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-10&endDate=2025-10-11&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with Wifi ![Suite, 1 King Bed, Jetted Tub (Oversized Room)](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/8a05d9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/0466e8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/8ea1a1cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/04dcd9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Inn Winchester 8.8/10 Excellent (642) "Clean room, friendly staff. " CA $142 CA $162 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Tullahoma-Hotels-Best-Western-Inn.h517564.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/37c03de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/bfd6d021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/a20dabb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194115/0eb1729a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful And Spacious Fully Renovated Farmhouse Winchester 9.4/10 Exceptional (29) "Great location for our family with young adult children to enjoy Targhee and Grand Tetons! Driggs was an unexpected treasure of a town, too." CA $175 CA $503 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Beautiful-And-Spacious-Fully-Renovated-Farmhouse.h78194115.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/df013be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/4290815c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/f44eb6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103950000/103947800/103947795/4269963e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Home w/ RV Hookups Winchester 8.6/10 Excellent (7) "Very clean highly recommend if you are looking to get away and relax " CA $187 CA $352 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Tiny-Home-W-RV-Hookups.h103947795.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/b916db0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/35b5b720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/87589e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844265/77bb0e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis on the Square Winchester 9.6/10 Exceptional (8) "Great accommodations in downtown Winchester! " CA $89 CA $214 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Old-Town-Oasis-Charm-Convenience-On-The-Square.h103844265.Hotel-Information) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/9cc274bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/de62040b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/3e529494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/79000000/78200000/78194100/78194091/ce0e0b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautifully Renovated Studio 2 miles from the Marina Winchester 9.8/10 Exceptional (15) "One-night stay to go to the lake next day. Close to the town square and about 15 min from Tim’s Ford Marina. " CA $91 CA $250 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winchester-Hotels-Beautifully-Renovated-Studio-2-Miles-From-The-Marina.h78194091.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/6ccd36a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/5a194f67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/1f2a6628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108476300/108476215/3cab0c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lakeside Getaway Winchester 9.6/10 Exceptional (5) "Incredible " CA $76 CA $678 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-The-Lakefront-Getaway.h108476215.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/5e9f2180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/5e255398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/129115b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103850000/103844300/103844252/70246f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester's Premier Downtown Loft! Winchester 9.6/10 Exceptional (8) "We thoroughly enjoyed our stay in this comfortable and beautiful apartment, right in the heart of Winchester. It’s walkable to several restaurants and a great ice cream shop. Check-in and communication were smooth. " CA $97 CA $224 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Winchester-Hotels-Winchesters-Premier-Downtown-Loft.h103844252.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/f2f49cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/606af038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/edfc7e0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108930000/108926900/108926864/5c6ce0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview Luxe - Lake Access + Pool Winchester 10/10 Exceptional (3) "Beautiful home. Very well kept. Hosts were very helpful. Short distance from restaurants and town square. " CA $213 CA $846 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Winchester-Hotels-Lakeview-Luxe-In-Gated-Barefoot-Bay-Steps-To-Lakefront.h108926864.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/be1f9671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/33c98354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/995b6b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110010000/110001600/110001577/57778f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxurious Lakefront Home- Marina, Boats, and Kayaks! Winchester 10/10 Exceptional (1) "We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again." CA $82 CA $684 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Luxurious-Lakefront-Home-Marina.h110001577.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/519b63fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/dcc8c8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/21ff0fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78200000/78194200/78194127/178d4db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Renovated Home with Open Floor Plan and Large Lot Winchester 9.0/10 Wonderful (16) "Peaceful, relaxing and pet friendly great location!" CA $126 CA $435 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Winchester-Hotels-Gorgeous-Renovated-Home-With-Open-Floor-Plan-And-Large-Lot.h78194127.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=2025-10-24&endDate=2025-10-25®ionId=177515&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Red Roof Inn Monteagle - I-24](//images.trvl-media.com/lodging/1000000/20000/11800/11756/67fa466b_y.jpg) ### Red Roof Inn Monteagle - I-24 10/10 Excellent "Away from road nice and quiet" [](https://expedia.ca/Tullahoma-Hotels-Red-Roof-Inn-Monteagle-I-24.h11756.Hotel-Information) ![The Smokehouse Lodge and Cabins](//images.trvl-media.com/lodging/1000000/580000/574500/574462/d6395701_y.jpg) ### The Smokehouse Lodge and Cabins 10/10 Excellent "Loved everything about the place and the area! My only complaint was that the bar/grill wasn’t open while we were there." [](https://expedia.ca/Tullahoma-Hotels-The-Smokehouse-Lodge-And-Cabins.h574462.Hotel-Information) ![Best Western Inn](//images.trvl-media.com/lodging/1000000/520000/517600/517564/8a05d9db_y.jpg) ### Best Western Inn 10/10 Excellent "Clean room, friendly staff. " [](https://expedia.ca/Tullahoma-Hotels-Best-Western-Inn.h517564.Hotel-Information) ![The Sewanee Inn](//images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/254f5123_y.jpg) ### The Sewanee Inn 10/10 Excellent "This hotel is nice! It was nice that the rooms are on one side and the restaurant is on the other. Beautiful lobby and entryway. There was a fire going in the lobby when we arrived which made it feel cozy. The beds were soft which made for a great nights sleep! We definitely would stay here again! We stayed here to go to The Caverns for an event so it was ideal location." [](https://expedia.ca/Tullahoma-Hotels-The-Sewanee-Inn.h7101157.Hotel-Information) ![Microtel Inn & Suites by Wyndham Manchester](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916021/4fbfd2df_y.jpg) ### Microtel Inn & Suites by Wyndham Manchester 10/10 Excellent "Very clean and had a nice selection of breakfast items. Easy to get to from interstate. " [](https://expedia.ca/Tullahoma-Hotels-Microtel-Inn-Suites-By-Wyndham-Manchester.h1916021.Hotel-Information) ![Best Western Fayetteville Inn](//images.trvl-media.com/lodging/1000000/10000/7100/7100/060b2bd3_y.jpg) ### Best Western Fayetteville Inn 10/10 Excellent "Pleasantly surprised with the renovations. The shower pressure was great. " [](https://expedia.ca/Tullahoma-Hotels-Best-Western-Fayetteville-Inn.h7100.Hotel-Information) ![Sleep Inn & Suites Manchester near Arnold AFB](//images.trvl-media.com/lodging/3000000/2720000/2716700/2716644/7de41e72_y.jpg) ### Sleep Inn & Suites Manchester near Arnold AFB 10/10 Excellent "Great bed, quiet neighborhooo." [](https://expedia.ca/Tullahoma-Hotels-Sleep-Inn-And-Suites-Manchester.h2716644.Hotel-Information) ![Comfort Suites Manchester near Arnold AFB](//images.trvl-media.com/lodging/3000000/2570000/2561100/2561048/527e1a97_y.jpg) ### Comfort Suites Manchester near Arnold AFB 10/10 Excellent "Great hotel with very friendly staff. " [](https://expedia.ca/Tullahoma-Hotels-Comfort-Suites-Manchester.h2561048.Hotel-Information) ![Best Western Shelbyville Inn and Suites Celebration Inn](//images.trvl-media.com/lodging/1000000/20000/13000/12971/e9125ab2_y.jpg) ### Best Western Shelbyville Inn and Suites Celebration Inn 10/10 Excellent "Very good overall . No complaints . 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