Title: Book the Best ROMANTIC Hotels in Winchester, TN from CA $85 - 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 $85 ![](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 Romantic Hotels Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=177515&startDate=2025-10-10&endDate=2025-10-11&adults=2&travelerType=ROMANTIC&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&travelerType=ROMANTIC&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&travelerType=ROMANTIC&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&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) ![1 Bedroom Timber Frame Cabin | Exterior](https://images.trvl-media.com/lodging/1000000/580000/574500/574462/16c47c0d.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 (1138) "Rustic, private, dog friendly cabin was great!" CA $74 CA $85 total includes taxes & fees Oct 28 - Oct 29 [](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) ![Free daily full breakfast](https://images.trvl-media.com/lodging/7000000/6620000/6619800/6619724/455d24c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Kimball Jasper 9.0/10 Wonderful (617) "It was wonderful " CA $160 CA $183 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chattanooga-Hotels-Hampton-Inn-Kimball.h6619724.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) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/30000000/29490000/29482500/29482406/ae72547f.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) ### A very rustic converted pole barn unique cozy cabin Estill Springs 10/10 Exceptional (141) "Super awesome place to stay! The antiques were pretty cool to check out. I would totally recommend this place. " CA $133 CA $223 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Estill-Springs-Hotels-Our-Unique-Cozy-Cabin.h29482406.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/a6967d61.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) ![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 (378) "Beautiful boutique hotel" CA $315 CA $367 total includes taxes & fees Oct 26 - Oct 27 [](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) ![Grand Cabin](https://images.trvl-media.com/lodging/117000000/116670000/116662100/116662011/4ab96a75.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 $245 CA $282 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/South-Pittsburg-Hotels-Sasquatch-Farm.h116662011.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/f9e2cd0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/18ccf56c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/0a77e852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/60000000/59900000/59898700/59898638/2ffcabb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Calming Cabin: Relaxing | Park-Like | Close to Hikes, Waterfalls, The Caverns Tracy City 10/10 Exceptional (61) "Everything we needed for a quick weekend visit with family in the area!" CA $121 CA $290 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Monteagle-Hotels-Calming-Cabin-Comfy.h59898638.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) ![TV](https://images.trvl-media.com/lodging/73000000/72290000/72284600/72284515/cbd1c13b.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 9.8/10 Exceptional (7) "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 $141 CA $395 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Tracy-City-Hotels-Shore-Beats-Work-At-The-Retreat-At-Waters-Edge.h72284515.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 $138 CA $375 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Monteagle-Hotels-Cozy-Cottage-At-The-Retreat-At-Deer-Lick-Falls.h64107466.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/73000000/72290000/72284500/72284494/faa75697.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 (12) "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 $141 CA $395 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Tracy-City-Hotels-Lakeview-Oasis-At-The-Retreat-At-Waters-Edge.h72284494.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18800000/18790500/18790418/d24fc917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18800000/18790500/18790418/ab9f588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18800000/18790500/18790418/87391f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18800000/18790500/18790418/a4296817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast Mulberry 10/10 Exceptional (44) "Beautiful property and wonderful proprietors." CA $244 CA $403 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Mulberry-Hotels-Cozy-Cottage-At-Lavender-Farm-Near-Jack-Daniels-Distillery.h18790418.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&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![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 Smokehouse Lodge and Cabins](//images.trvl-media.com/lodging/1000000/580000/574500/574462/d6395701_y.jpg) ### The Smokehouse Lodge and Cabins 10/10 Excellent "Rustic, private, dog friendly cabin was great!" [](https://expedia.ca/Tullahoma-Hotels-The-Smokehouse-Lodge-And-Cabins.h574462.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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