Holiday houses 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

4.96 out of 5 average rating, 28 reviews

Apartment in Winchester

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!

4.94 out of 5 average rating, 155 reviews

Home in Manchester

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.

5 out of 5 average rating, 44 reviews

Tiny home in Winchester

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.

4.96 out of 5 average rating, 268 reviews

Cabin in Estill Springs

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

4.94 out of 5 average rating, 35 reviews

Home in Cowan

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!

Superhost

Apartment 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.

4.97 out of 5 average rating, 37 reviews

Barefoot Retreat w/kayaks/SUP/Game Room/Pool

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This cozy cottage is in a beautiful gated community and sits close to the lake. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for kayaks and paddleboards that we include for you! This beautiful home boasts indoor/outdoor fireplaces & fire pit for your family to enjoy! You are also centrally located and only 5 minutes from Twin Creeks Marina and downtown!

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.

Superhost

Apartment in Winchester

New place to stay

Clean Lines and Simple Comfort

This 2 bedroom, 2 bath apartment 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.

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.

4.98 out of 5 average rating, 180 reviews

Home in Chattanooga

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.

Holiday rentals for every style

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Stylish accommodation and amenities

Popular amenities for Winchester holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winchester

5 out of 5 average rating, 22 reviews

Luxury 3BR lakeside escape

MikeRating, 5 stars3 days ago

A very beautiful home. Well stocked and clean. We would definitely stay again if the need arises.

5 out of 5 average rating, 10 reviews

The Hangout on Heath Lane

AngelinaRating, 5 stars1 day ago

Corey was super responsive and friendly. The place was clean and cozy. Would definitely book again!

4.88 out of 5 average rating, 16 reviews

TC Easy Breeezee

LauraRating, 5 stars2 weeks ago

Lovely home, perfect for me and my toddler. He especially loved the bunk bed room. Plenty of towels, good coffee marker and nice bedding. Communication with the owner was pleasant and clear. I’d recommend and would stay at this home again.

5 out of 5 average rating, 13 reviews

Home in Estill Springs

Timberhill Home-Walk to the Lake!

NoyRating, 5 stars3 weeks ago

This place was exactly as listed and was very comfortable and cozy! The location was great and we had a great time staying here with my family 😊

4.97 out of 5 average rating, 60 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

AmandaRating, 5 stars2 weeks ago

Linda’s house on the Lake was one of the best. Linda herself went out of her way to make sure we felt at home and added things to kitchen that would accommodate our very late check in with kids. She also had kayaks and a paddle board to use out on the lake which my kids thought was the best part. We felt the house was very clean and yet had everything we needed for a group of 7. Tons of extra towels and bedding. The kitchen was fully stocked with everything you would need to cook. And she had a book that had all sorts of recommendations and extra information. Then on top of that she was fabulous at communicating and checking in if there was anything else we needed.

5 out of 5 average rating, 11 reviews

Charming Barefoot Bay Bungalow

JenniferRating, 5 stars10 months ago

Beautiful place looks like brand new construction, great location, everything was done with excellence!

4.96 out of 5 average rating, 76 reviews

Cabin in Monteagle

Modern Monteagle A-frame with Hot Tub

WendyRating, 5 stars2 weeks ago

Loved this place I definitely recommend! It was private but also had other homes nearby so you weren’t completely alone in the woods haha. They recommended amazing hiking spots that my husband and I went to see and it was so fun. We’re from Illinois so it’s mostly corn fields so hiking through mountains and seeing the waterfalls was just an amazing experience. Overall this home was lovely and our hosts were friendly/great people. Must see.