Holiday houses in Winchester
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Top-rated holiday rentals in Winchester
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Winchester's Premier Downtown Loft!
Escape to The Heritage Lofts, just off of the thriving Winchester square. Only minutes from Tims Ford Lake, this fabulously-renovated apartment has all of the comfort and amenities you need to feel right at home during your stay in Winchester. See the local scene in style with one of our bike or paddle board rentals, and shop til you drop on our thriving downtown square. Then grab a meal before relaxing in the comfortable confines of your spacious loft. There isn't a better spot to stay in town!
Lakefront Haven | Hot Tub | Kayaks, Firepit
Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square
Location, location, location!
No detail has been left undone when it comes to cleanliness, decor, or amenities. Tims Ford Boat Launch <1/4 mile, walk to Twin Creeks, Walk to historic Winchester square (< 1mile) where you can enjoy several dining/shopping options. Hike the mountains, tour Sewanee, Jack Daniels or Dickel, boat at Tims Ford, float the Elk, or just relax at this oh so quaint home. The location is also convenient for concerting at The Caverns. If you are tired of boring and unclean rentals, look no further!
Tiny House
You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.
Best Views on Lake, TIki Hut, Boat Rental + More
If you are looking for the perfect getaway to a luxury lake home that has countless amenities and postcard like views then look no further! This newly renovated lake front home boasts the best views on the lake, tiki hut, multiple outdoor decks, covered patio, hot tub, game room, theatre, kayaks, SUPs and plenty more! We even have a 2022 Crest tritoon with a 200 HP motor that is available to rent for experienced boaters! This is truly a one of kind property. We look forward to serving you!
Private dock/gazebo on quiet cove. Tims Ford Lake!
Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!
Barefoot Dreams
Barefoot Dreams is a newer custom lake home vacation rental in the gated community of Barefoot Bay on Tims Ford Lake in Winchester TN. This luxury lake house rental is perfect for families and groups seeking a Tims Ford Lake cabin, waterfront getaway, or Tennessee lake vacation home. Enjoy stunning water views, modern design, and an open-concept layout. Ideal for boating, fishing, swimming, and lakefront relaxation. A peaceful yet fun-filled family vacation rental on the lake.
The Modern Mainstay at Barefoot Bay
Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.
Clean Lines and Simple Comfort
This 2 bed, 2 bath apartment duplex is located just two miles from Tims Ford Lake. Whether you’re in town for a weekend or an extended stay, this space offers everything you need for a relaxing and comfortable visit. Each room features a comfortable queen bed, fresh linens and ample closet space. The kitchen is stocked with cookware, stainless steel appliances, and a coffee maker for your morning brew. Book your stay and enjoy an experience that’s clean with a blend of style.
The Hangout on Heath Lane
Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.
Lakeside Manor Retreat
Enjoy your stay at this gorgeous modern style sanctuary, nestled on 2 acres near Tim’s Ford Lake. A private oasis, only 2 blocks from Twin Creeks Community & 6 blocks from Historic Downtown. Featuring gorgeous kitchen w/bar, wine fridge, ice machine, granite islands ,2 master suits with XL soaking tubs, 4 bedrooms, 3.5 baths, 7 TVs, air hockey & more! Sleeps 12. Plenty of parking. Message us with any questions. Thank you for your interest in Lakeside Manor Retreat
Basecamp Retreat TimsFordLake
Welcome to Basecamp Retreat! Modern lake luxury on Tims Ford Lake. This 3-bedroom, 2.5 bath cozy retreat, located in the gated community of Barefoot Bay, is the perfect home base for your visit. Offering modern comforts and convenience in a prime location with picturesque lake views, Basecamp provides a comfortable and inviting space to relax and recharge. Located 2 miles from Twin Creeks Marina & Resort and 1 mile from downtown Winchester.
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
HideAway @ Tim's Ford Lake 4BR/3BA - Private Dock
The Yellow Cottage by Tims Ford Lake
Cottage on Cedar
Lakefront luxury retreat- with private dock.
Huge lakefront retreat w/ views, dock, decks & bar
AquaHallics Retreat 2
The Owl’s Nest: A Private Mountain Top Escape
Just Around the Corner
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $303 NZD | $274 NZD | $318 NZD | $324 NZD | $436 NZD | $528 NZD | $526 NZD | $475 NZD | $363 NZD | $373 NZD | $364 NZD | $307 NZD |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
Frequently Asked Questions
What are the best places to stay in Winchester?
Vacation rentals around Winchester’s downtown neighborhoods and near the lakeside provide relaxed settings. Areas close to parks, shops, and community spaces are frequently favored by visitors.
What are the best things to do in Winchester with kids?
Kids can explore playgrounds, enjoy lakeside parks, and participate in fishing or boating. Attending seasonal events and visiting small museums around the town square is also popular with families.
What are some of the best things to do in Winchester?
Explore the historic town square, enjoy water activities at area lakes, and visit small museums or local shops. Outdoor recreation, seasonal festivals, and community gatherings are frequently suggested.
How is the weather in Winchester?
Winchester has cooler winters around 32–51°F (0–11°C), and warmer summers near 71–91°F (22–33°C), with rainfall throughout the year. Spring and fall bring comfortable temperatures and are popular seasons for outdoor activities.
When is the best time to visit Winchester?
Late spring and early fall are often recommended, with milder temperatures between 50–84°F (10–29°C) and less rainfall. Summer draws visitors for outdoor recreation and community festivals near the lake.
What are the best places to visit in Winchester?
Explore Winchester’s historic town square, lakeside parks, and small museums that share local heritage. Antique shops and public green spaces frequently attract visitors year-round.
What are some hiking trails in Winchester?
Winchester has easy nature walks and longer trails around local parks and the lake area. Trailheads frequently include shaded paths, water views, and spaces for birdwatching.
What are some family activities we can do in Winchester?
Families can enjoy lakeside parks, fishing, playgrounds, and small museums around Winchester. Seasonal events on the town square and water activities at area lakes are often favorite outings.
What are some of the best day trip ideas from Winchester?
Consider exploring natural areas, state parks, or neighboring small towns with distinct local culture and shops. Regional wineries, historic sites, and hiking trails are frequently suggested for day outings.
Are there any pet friendly accommodations available in Winchester?
Winchester has pet friendly vacation rentals in neighborhoods near parks and the lake. Some hosts also provide outdoor spaces or walking trails for guests traveling with pets.
What are some local tips for visiting Winchester?
Locals suggest exploring both downtown shops and the lake area, especially for outdoor recreation. Arrive early for community events, and enjoy regional foods at neighborhood diners for an authentic experience.
What is Winchester known for?
Winchester is known for its historic town square, nearby lakes, and regional traditions rooted in Southern culture. The area often draws visitors for fishing, boating, and community celebrations.
What are the best hidden gems to explore in Winchester?
Explore local antique shops, small-town museums, and quiet nature trails around Winchester. Some visitors discover riverside parks and scenic spots just outside the main town area.
What are the best foods to try in Winchester?
Winchester has locally rooted Southern dishes, including barbecue, fried catfish, and seasonal produce. Bakeries and cafes frequently suggest homemade pies and country breakfasts as regional specialties.
What should I bring for a trip to Winchester?
Pack comfortable clothing suitable for outdoor activities, as local weather varies from 32–91°F (0–33°C) through the year. Include sturdy shoes for hiking, sun protection, and light rain gear, especially in spring and summer.
What is the nightlife in Winchester like?
Winchester’s nightlife centers around casual gathering spots, including locally run cafes, laid-back bars, and venues with live music. Social evenings often take place near the town square or around lakeside restaurants.
What are the most popular events or festivals in Winchester?
Winchester frequently hosts community fairs, seasonal festivals, and locally rooted celebrations around the town square. Summer often features events near public parks and lakefront areas, drawing both residents and visitors.
Are there family friendly vacation rentals in Winchester?
Winchester has a selection of vacation rentals that welcome families, with some homes featuring spacious layouts, yards, and access to nearby parks. Look for stays around peaceful neighborhoods or near recreational lakes.
Quick stats about holiday rentals in Winchester
Total holiday rentals
Explore 130 holiday rentals in Winchester
Nightly prices starting at
Winchester holiday rentals start at $17 NZD per night before taxes and fees
Verified guest reviews
Over 4,020 verified reviews to help you choose
Family-friendly holiday rentals
130 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 40 rentals that welcome pets
Holiday rentals with a pool
40 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
130 of Winchester holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals
4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Chattanooga Choo Choo
- Coolidge Park
- Hunter Museum of American Art
- Point Park
- South Cumberland State Park
- Creative Discovery Museum
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Old Stone Fort State Archaeological Park
- U.S. Space & Rocket Center
- Von Braun Center, North Hall
- Short Mountain Distillery
- Cathedral Caverns State Park
- Cumberland Caverns
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Chattanooga Convention Center
- Tennessee River Park