Holiday rentals in Winchester

4.82 out of 5 average rating, 131 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

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

4.9 out of 5 average rating, 10 reviews

Dry Jack Tim- Water Views, Pool, Outdoor Fireplace

This beautiful Lake home is located in the pristine community of Twin Creeks, has water views, steps from the pool, and 3 min to the marina. Bring your own boat to launch at the marina private dock. No boat? no problem! The Marina offers the following rentals: pontoon boats, kayaks and paddle boards. The on-site store will take care of all of your boating needs including gas, beverages, sunscreen, snacks etc… Drafts and Watercrafts bar and grill frequently features live music on the weekends.

4.96 out of 5 average rating, 28 reviews

Flat 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!

5 out of 5 average rating, 42 reviews

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private

Welcome to your retreat at Tims Ford Lake! Hidden away on 2.5 acres, surrounded by trees, complete privacy with no neighbors in sight! Enjoy peace and quiet, TVA land between you and the lake. Plenty to do..whiskey trail, fishing/kayaking Elk River, boating Tims Ford Lake to name a few! 16 minutes to Jack Daniel's Distillery Property is less than a mile from boat ramp! Ride the UTV down to the lake! ***IMPORTANT: For UTV & craft info, please see below in Other Things to Note for details.

5 out of 5 average rating, 47 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.

Superhost

5 out of 5 average rating, 4 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

Welcome to Sunset Cottage, a spacious and serene lakeside escape nestled in the heart of Winchester. Located less than a mile from the town square, this charming cottage offers both the tranquility of lakefront living and the convenience of nearby dining and shopping. Relax as you take in breathtaking sunset views from the back covered porch. With a private boat dock, you can easily set out for a day on the water. Designed for comfort and relaxation, Sunset Cottage is the ideal getaway.

4.96 out of 5 average rating, 119 reviews

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!

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

Flat 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.

4.91 out of 5 average rating, 11 reviews

Flat in Winchester

Winchester Nomad Downtown Suites On The Square!

Recreated mid-century charm centrally located on the square in Downtown Winchester. Every room has unique themes, and the living room features some great arcade classics. Within a few steps of 1930 The Oldham Theater, restaurants, and coffee! Near Jack Daniels Distillery, Caverns, Bonnaroo, Tims Ford Lake & Bear Trace Golf Course. Also, short drive of great hikes, other outdoor activity. 1.5 hr to Chattanooga 1.5 hr to Nashville Ready for you to make memories!

5 out of 5 average rating, 8 reviews

Cottage in Winchester

Waterfront Cottage #7 - "Dog Daze" PET friendly!

Discover serenity at our Cottage nestled directly on the shores of Tims Ford Lake. Experience ultimate privacy in this hidden gem, where you'll be enveloped by nature's beauty with all the conveniences of our Resort amenities. Step inside to find a charming space adorned with a unique theme, creating an atmosphere of warmth and character. With every modern amenity provided, from a fully-equipped kitchen to cozy sleeping quarters, we ensure you will feel right at home.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

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Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Winchester holiday rentals

Kitchen

Wifi

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 stars1 week ago

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

5 out of 5 average rating, 11 reviews

The Hangout on Heath Lane

AngelinaRating, 5 stars1 week ago

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

4.91 out of 5 average rating, 11 reviews

Twin Creeks Getaway, Pet Friendly!

CharlotteRating, 5 stars1 month ago

We have stayed here twice and it was great both times. We feel right at home. We love sitting on the front upstairs porch in the mornings and evenings. The inside is very nice and comfortable and has everything we need. It's a great location to walk down to the marina for lunch or dinner and to rent a boat. However, it is far enough away that you don't feel crowded by the busyness of the marina.

4.97 out of 5 average rating, 60 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

AmandaRating, 5 stars4 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.

4.93 out of 5 average rating, 54 reviews

Tim’s Ford Lake 6BR private dock near Twin Creeks

KathyRating, 5 stars4 weeks ago

Our stay at Julie’s place was so good. All our family was there except one granddaughter. We had a great time on the water in spite of some rain. We rented a pontoon for Saturday and it was a hit for everyone. The house is well stocked and very spacious. It was helpful to have access to 2 kitchens. But just know there is nothing in the way of dishes or utensils downstairs. The game area was awesome and enjoyable for everyone. The downstairs bathroom needs a new shower because even though it’s clean it looks dirty. We had an issue with the AC when we got there and Julie jumped right on it and had someone there that night. (Even though she was in Italy!). We also found that the downstairs patio area had not been cleaned in a while and cushions were very dirty. We had to clean the two porches floors and cushions but I think no one had used the house for a while. Again she got someone there the next morning who power washed the patio and cushions outside. Julie is a great host.

5 out of 5 average rating, 4 reviews

Lake Lagoon

CarlRating, 5 stars3 months ago

VERY Nice house, with a flat lot on Tims Ford Lake, no stairs to the water! The house was very upscale and won't disappoint you compared to the photos. Very nice beds, tv's in all bedrooms, big spaces for a small home. Back porch, hot tub, and privacy all stood out as fantastic. The house is a few streets away from downtown Winchester which has a theater, restaurants, coffee shops, all you need! I would definitely stay here again!

4.95 out of 5 average rating, 20 reviews

Huge lakefront retreat w/ views, dock, decks & bar

SummerRating, 5 stars6 months ago

Beautiful home with high end finishes. Lots of space for all to sleep, hang out, play games, etc. One bedroom is open to the stairs that leads to the room with 6 beds so that bedroom has little privacy. (They did provide a foldable screen.) Industrial kitchen made meal times a cinch. We had 15 in our group and there were plenty of beds for everyone.