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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Farm stay in Shelbyville

4.99 out of 5 average rating, 141 reviews

Circle C Alpaca Farm - Entire apartment

No cleaning fees and we don’t ask our guests to do chores! Enjoy our detached 1-bedroom apartment on our 21-acre working alpaca farm. Country peace but close to Shelbyville, Tullahoma, and Lynchburg. Sleeps up to 3 guests on a king-sized bed and a full-size pull-out couch. There is also a twin-sized roll-away bed stored in the bedroom's walk-in closet. During your stay enjoy feeding, petting, or just watching the alpacas or enjoy a round of disc golf on the private 18 hole disc golf course).

Home in Manchester

4.91 out of 5 average rating, 114 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.

Cabin in Estill Springs

4.96 out of 5 average rating, 252 reviews

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.

Home in Winchester

4.93 out of 5 average rating, 107 reviews

Beautiful Tims Ford lakefront home

Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

Home in Winchester

4.96 out of 5 average rating, 117 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!

Cabin in Winchester

4.82 out of 5 average rating, 157 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

Cabin in Decherd

4.98 out of 5 average rating, 324 reviews

Scandanavian Style/ hot tub/view/gameroom/fire pit

This modern, Scandinavian style cabin, sits on 20 private acres at a 1360 ft. elevation. The style sets it apart from other cabins. It is 13 miles from The Caverns concert venue (about a 20 minute drive). The cabin is close to Sewanee, which has many hiking trails and is home to The University of the South (about 7 miles from our cabin/ a 16 minute drive.) Other local hiking and recreation options include the South Cumberland State Park and Tims Ford State Park.

Cabin in Tullahoma

4.95 out of 5 average rating, 147 reviews

Cozy Cabin Near Tims Ford Lake & Jack Daniel's

A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

Home in Winchester

4.92 out of 5 average rating, 116 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.

Barn in Tullahoma

4.97 out of 5 average rating, 153 reviews

The Barn @ Dreamcatcher Farm

Make sure to “heart” our listing so you can find us when you are ready to book. Did someone say baby goats?!?! Live the farming dream in Middle Tennessee on Dreamcatcher Farm. Our 13 acre farm is home to Nigerian Dwarf goats, Santa Gerturdus cattle, a couple of horses, and the Labs and barn cats that run the operation. Come enjoy some down time in a quiet country setting with friendly farm animals.

Guest suite in Manchester

4.98 out of 5 average rating, 381 reviews

Creekside at Rutledge Falls

Cozy nest right on the creek. Lots of privacy. Hiking trails and Waterfalls nearby. Listen to the water from a porch swing overlooking the creek. We have a double recliner for movies and popcorn. This efficiency apartment has a private entrance with private covered porch and a full kitchen. Work area with Wi-Fi. Pets are welcome - must be free of fleas and ticks.

Home in Estill Springs

5 out of 5 average rating, 33 reviews

Lakeside Paradise - Waterfront View & Private Dock

With private waterfront access and million-dollar lakeside views, this sunny slice of paradise is one of Estill Springs' most exclusive secrets. Indulge yourself with our waterfront outdoor lounge, tiki lamps, private dock and boat slip, luxurious jacuzzi tub with spa jets, sleepy sunroom, charcoal grill, 4K TV's, and fully inspired gourmet chef's kitchen.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

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Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Winchester vacation rentals

Free parking on premises

Air conditioning

Stay near Winchester's top sights

Twin Creeks Marina44 locals recommend

Piezan Pizzeria Italiano25 locals recommend

Walnut Hill Coffee Company19 locals recommend

Drafts & Watercrafts19 locals recommend

The Oldham16 locals recommend

SUNRISE (The Breakfast Place)16 locals recommend

Other great vacation rentals in Winchester

Home in Winchester

5 out of 5 average rating, 9 reviews

Lakeview Luxe-Just Steps to Lake & Pool Cozy Chic

Home in Winchester

4.91 out of 5 average rating, 45 reviews

Lakefront 6br@ Tim’s Ford w/ dock near Twin Creeks

Home in Winchester

4.99 out of 5 average rating, 67 reviews

Best Home on Tims Ford - Private Dock - Hot Tub

Home in Winchester

5 out of 5 average rating, 17 reviews

The Modern Mainstay at Barefoot Bay

Home in Winchester

5 out of 5 average rating, 14 reviews

Lakeshore Modern- steps to water

Home in Winchester

5 out of 5 average rating, 21 reviews

On Water w/ Private Dock, Entire Home, sleeps 14

Farm stay in Lynchburg

4.98 out of 5 average rating, 54 reviews

Coneflower Cottage

Cottage in Tullahoma

4.99 out of 5 average rating, 69 reviews

Lakeside Family Fun Retreat!

Quick stats about vacation rentals in Winchester

Total rentals
130 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool

Frequently Asked Questions

Do house rentals in Winchester have free parking?
Absolutely! We offer over 90 house rentals with free parking in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 30 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Winchester?
Experience the best of Winchester with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winchester have a kitchen?
Absolutely! We offer over 90 house rentals with a kitchen in Winchester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Winchester?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Winchester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Winchester, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Winchester have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winchester?
Winchester has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Winchester have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 80 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore