
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.

Private Dock - Best Cabin Tims Ford Lake
Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

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.

Tennessee’s ONLY Luxury Safari Tent Getaway
Soak in sweeping mountain and valley views from your private hot tub at this remote, luxury safari tent. Unwind on a plush king bed, sip wine beside the glowing fire feature, and bask in unforgettable sunrises and sunsets. Surrounded by nature, peace, and starry skies, this hidden gem is the perfect escape. Just minutes from waterfalls and hiking, it’s glamping at its most magical—serene, stylish, and tucked far away from it all. Reconnect with what matters: nature, stillness, and yourself.

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.

The Nest at The Retreat @ Deer Lick Falls
The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

The Coalmont Cove - Romantic Lakefront Escape
The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. The Coalmont Cove is a tiny home that sits in the cove of a private lake. The definition of relaxation with adventure only minutes away, you'll find elevated decor, an inviting outdoor space, and beautiful scenery. The perfect retreat if you’re looking for a romantic getaway or a quiet place to disconnect or work remotely (1 GB fiber optic internet).

Sweet Dee's Tiny Home
FEATURES A HOT TUB! Relax in style at Sweet Dee's (formerly listed as The Alexander), a luxury tiny home in the Retreat at Deer Lick Falls. Serene, tranquil, rustic, wooded setting with relaxation stations throughout the community. The Retreat at Deer Lick Falls is a gated luxury tiny home community in southeast Tennessee. The community is only 15 minutes from the University of the South in Sewanee. Guests of the Retreat also have access to Retreat at Waters Edge and it's lake.

the tiny bungalow @ waters edge | tiny house
welcome to our favorite little bungalow. located in tracy city, tn @ the waters edge tiny house community. cozied in the woods, we love to host our guest not just with a retreat but an experience. we have deigned our place to have what you need, so you can show up and rest. our tiny bungalow is perfectly designed for that romantic getaway, a writers retreat, an escape for friends to connect over an open fire, or a family adventure hiking the trails + paddling out on the lake.

Cozy Cabin close to Tims Ford Lake & Jack Daniels
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.

Owl’s Nest Treehouse Getaway w/ Hot Tub & Fire Pit
Reconnect with nature at this unforgettable treehouse escape. One of the few treehouse cabins in Tracy City, located on 2 acres of beautiful wooded land. We are less than 1 mile from South Cumberland State Park with access to hiking trails, creeks, and Mountain views. Enjoy the sounds of the woods on our elevated deck, or relax in the private hot tub down below. The newly renovated outdoor space includes a grill, fire pit, pond & hanging egg chairs.

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.

Woodland Ct. Cottage
This one bedroom guesthouse is the perfect stay for you and your loved ones! Conveniently located in the heart of Tullahoma! Within walking distance of just about everything you need from grocery stores, restaurants, local coffee shops, and more! We are located just 20min from the famous Jack Daniels Distillery and 15 min from George Dickle! If you are interested in some nearby hiking be sure and check out Short Springs and Rutledge falls!
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

Luxury 3BR lakeside escape

Alpaca Ridge Ranch and Retreat

Lakeside Retreat at The Reserve w/ Golf Cart

Everly House in Deer Lick Falls

Serene Lake House Retreat with New Golf Cart

Cottage on Cedar

Cliffside Luxe Retreat w/Pool, Hot Tub, Views

Tims Ford Lake Getaway
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $246 SGD | $245 SGD | $249 SGD | $247 SGD | $333 SGD | $403 SGD | $402 SGD | $363 SGD | $277 SGD | $268 SGD | $290 SGD | $271 SGD |
| 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
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 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Winchester?
Experience the best of Winchester with our cottage rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Winchester have a kitchen?
Absolutely! We offer over 10 cottage 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 a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, 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 apartment rentals in Winchester have air conditioning?
Absolutely! We offer over 10 apartment 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 house rentals in Winchester have wifi?
Absolutely! We offer over 90 house 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 70 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 $26 SGD per night before taxes and fees

Verified guest reviews
Over 3,620 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
130 of Winchester holiday rentals include wifi 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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- Rentals with a washing machine and dryer Winchester
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- House rentals Winchester
- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Pet-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Family-friendly rentals Winchester
- Rentals with a firepit Winchester
- Rentals with lake access Winchester
- Rentals with a patio Winchester




