Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Superhost

Home in Winchester

4.82 out of 5 average rating, 130 reviews

Beautiful And Spacious Fully Renovated Farmhouse

Beautifully renovated 4 bedroom, 3 bathroom, spacious home. Roku TV, fast internet, large yard where you can see the sunrise in the back of the home and the sunset in the front of the home. Very close to the lake (less than 10 minute drive), close to many great nature spots, and University of the South, Downtown Winchester area, and the famous Jack Daniels Distillery. 8 people can be comfortably accommodated, and if extra sleeping arrangements are needed, we have a comfy couch! W

Top guest favourite

Home in Winchester

5 out of 5 average rating, 25 reviews

Cottage on Cedar

This beautiful 1930s cottage has been updated to resemble its old charm. Warm and cozy with incredibly comfortable beds and quality linens. Bedrooms have their on TVs along with main TV in the living area The bathroom is a tub/shower and is very spacious- supplied with towels, soap/ shampoos, hairdryer. Kitchen is fully furnished for cooking. Dishwasher a plus Granite countertops Keurig coffee maker Washer/ Dryer for your convenience. Cottage also has a new heat and air unit Gonna love this

Top guest favourite

Flat in Winchester

4.96 out of 5 average rating, 28 reviews

Unbeatable Charm & Convenience On The Square!

Escape to The Heritage Lofts, just off of the thriving Winchester square. Just minutes from Tims Ford Lake, this fabulous newly-renovated apartment has it all! Stock up for your next adventure downstairs at Russells Outdoor and Trading Company then head next door to Walnut Hill for coffee and breakfast before setting out for the day. Grab a bite to eat at Jefferson's a few doors down and relax in the comfortable confines of your cozy king-sized bed. There isn't a more convenient spot in town!

Top guest favourite

Home in Manchester

4.94 out of 5 average rating, 155 reviews

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Top guest favourite

Tiny home in Winchester

5 out of 5 average rating, 44 reviews

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.

Top guest favourite

Townhouse in Winchester

5 out of 5 average rating, 5 reviews

Lovin Lake Life

Relax and unwind at this spacious 5BR/7-bed townhome just 1-2 minutes from Twin Creeks Marina & Dry Creek Beach! Take the complimentary golf cart and relax by the pool or head to the marina to rent a boat, shop at the store, or eat/drink at Drafts & Watercrafts Bar & Grill. Enjoy cozy furnishings, relax on the screened in porch, or challenge your group to a game of ping pong. This home is perfect for families, groups, and lake lovers looking for a fun and easy getaway in Winchester, TN.

Top guest favourite

Home in Cowan

4.94 out of 5 average rating, 35 reviews

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. We are a 10 minute drive to Tim’s Ford Lake, Twin Creeks Marina & historic downtown Winchester + 15 minutes from University of the South. This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Enjoy the private, quiet back porch with a view of the pond and the farm. Beautiful sunrise + sunset views too!

Top guest favourite

Home in Winchester

5 out of 5 average rating, 19 reviews

1940's Cottage Near Square/Lake

WELCOME to this beautiful, newly renovated COTTAGE near the Winchester Square and Tim's Ford Lake. This Historic Home, built in 1948 is full of CHARACTER but yet modern and stylishly furnished. Within walking distance to the Winchester Square and just 1 mile from Twin Creeks Marina this beautiful home in convenient, comfortable, and welcoming for all guests. This is the home that you have been looking for that is BUDGET friendly but also packed with AMENITIES in the perfect location!

Superhost

Flat in Winchester

4.84 out of 5 average rating, 45 reviews

Just Around the Corner

You will love this duplex centrally located in town off the square by the old jail for all the history buffs. It is a historical landmark overlooking the lake. I know the family that lived upstairs in the old jail and their father was the jailer. They have a lot of old stories to tell. It is within walking distance to great restaurants, grocery store, shops and businesses on the square and it is pet friendly! It can sleep 6, 2 Queen beds and a couch that pulls out to a full size bed.

Top guest favourite

Home in Winchester

5 out of 5 average rating, 23 reviews

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.

Guest favourite

Home in Winchester

4.93 out of 5 average rating, 122 reviews

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Guest favourite

Home in Chattanooga

4.98 out of 5 average rating, 181 reviews

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS and WITHOUT TV!*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.