Title: Book the Best ROMANTIC Hotels in Winchester, TN from CA $82 - Winchester Romantic Getaways | 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 Romantic Hotels in Winchester, TN from CA $82 ![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 availability on Winchester Romantic Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-09-27&endDate=2025-09-28&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-09-28&endDate=2025-09-29&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-03&endDate=2025-10-05&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Romantic Hotels ![Coffee/tea maker](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/d6395701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/70506202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/c7d55e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/aee2f9a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Smokehouse Lodge and Cabins Monteagle 8.6/10 Excellent (1137) "Great place!" CA $71 CA $82 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Tullahoma-Hotels-The-Smokehouse-Lodge-And-Cabins.h574462.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/bdd47495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/e7b9c704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/c88996d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/af5232e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Kimball Jasper 9.0/10 Wonderful (614) "Fantastic Stay 5/5, stays true to the Hampton Brand" CA $165 CA $189 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chattanooga-Hotels-Hampton-Inn-Kimball.h6619724.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/254f5123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/46510bb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/6d79c1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/8000000/7110000/7101200/7101157/0c3af528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sewanee Inn Sewanee 9.8/10 Exceptional (375) "Nice place" CA $320 CA $373 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Tullahoma-Hotels-The-Sewanee-Inn.h7101157.Hotel-Information) ![Couples treatment rooms, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/c153b036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![58-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/59be8a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/6e667d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/c3f6850d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sasquatch Farm South Pittsburg 8.0/10 Very good (1) "The cabin was fine but they said it was a 2 bedroom. It wasn't. Couch is second bedroom. Next . Not equipped at all . Nothing. No toilet paper . No plates . No paper towel . No cutlery . The grill worked but a hassle to hook up . No extra blankets . None . Had to borrow the top sheet from the bedroom for a blanket . No napkins . Nothing . " CA $244 CA $280 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/South-Pittsburg-Hotels-Sasquatch-Farm.h116662011.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64110000/64107500/64107466/7b191bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64110000/64107500/64107466/44e6338d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64110000/64107500/64107466/e80ce4ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64110000/64107500/64107466/57bdc8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage at The Retreat at Deer Lick Falls Monteagle 10/10 Exceptional (17) "Had an awesome time staying at this location. Perfect for a concert at the Caverns and hiking the the South Cumberland. " CA $133 CA $360 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Monteagle-Hotels-Cozy-Cottage-At-The-Retreat-At-Deer-Lick-Falls.h64107466.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/33a79d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/81e97b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/75a48c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/5d6fb7f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A very rustic converted pole barn unique cozy cabin Estill Springs 10/10 Exceptional (141) "We had a great stay! " CA $132 CA $222 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Estill-Springs-Hotels-Our-Unique-Cozy-Cabin.h29482406.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72284600/72284515/e0a9d38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72284600/72284515/0d01620d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72290000/72284600/72284515/48971531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72284600/72284515/5e88937f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shore Beats Work at The Retreat at Water's Edge Tracy City 10/10 Exceptional (5) "The resort area is beautiful and clean. There are multiple homes for rent within walking distance of each other. Our family rented 3 homes. The lake setting with outdoor amenities is relaxing and enjoyable. Everything about the house we rented was clean, well maintained and beautifully decorated. It was comfortable and relaxing." CA $140 CA $388 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Tracy-City-Hotels-Shore-Beats-Work-At-The-Retreat-At-Waters-Edge.h72284515.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/03026449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/4573d11f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/d7bace20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/2ff79d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Calming Cabin: Peaceful | Country Chic | Hikes, Waterfalls, The Caverns Nearby Tracy City 10/10 Exceptional (61) "Close to the caverns and hiking, " CA $99 CA $263 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Monteagle-Hotels-Calming-Cabin-Comfy.h59898638.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72290000/72284500/72284494/c18a7f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72290000/72284500/72284494/75cb2387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72290000/72284500/72284494/885c9544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72290000/72284500/72284494/cdbefc0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview Oasis at The Retreat at Water's Edge Tracy City 9.6/10 Exceptional (11) "Lakeview Oasis is just as the name describes. This tiny home is charming and comfortable. I highly recommend it for anyone who seeks a quiet getaway." CA $140 CA $388 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Tracy-City-Hotels-Lakeview-Oasis-At-The-Retreat-At-Waters-Edge.h72284494.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=2025-10-11&endDate=2025-10-12®ionId=177515&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![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 "Great value for the money" [](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 "Thank you for an excellent stay!" [](https://expedia.ca/Tullahoma-Hotels-Best-Western-Inn.h517564.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Winchester? > Are you in need of a romantic getaway? You might consider checking out some of the nearby sights and attractions such as Twin Creeks Marina, Tim's Ford Marina, or Tims Ford State Park. If you'd like to stay close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Winchester? > If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winchester: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Winchester is 64 inches. ### What is there to do in Winchester? > There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Winchester has to offer. A visit to Twin Creeks Marina, Tim's Ford Marina, or Tims Ford State Park might be just the ticket when you're checking out the sights. ### What's the best way to get to Winchester and around town during my romantic getaway? > This information about transportation options in Winchester might help your romantic trip go off without a hitch: The closest major airport is Chattanooga Metropolitan Airport (CHA), located 52.8 mi (85 km) from the city center. 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