Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

Home in Winchester

5.0 out of 5 average rating, 23 reviews

Cozy Lake Cottage W/ Kayaks, SUPs, Pool & Firepit

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 has lake views from the front porch. 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 also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

Feb 6 – 13

ﺩ.ﺇ498 per night

Guest favorite

Cabin in Estill Springs

4.95 out of 5 average rating, 239 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.

Mar 27 – Apr 3

ﺩ.ﺇ409 per night

Guest favorite

Cabin in Lynchburg

4.95 out of 5 average rating, 146 reviews

Cozy Cabin on Tims Ford Lake

Come stay at a hand built log cabin nestled right on Tims Ford Lake. Enjoy a cup of coffee and watch birds fly in a rocking chair on the front porch. Relax in the porch swing as you see fish jump from the water. Grill out on the back porch while watching the sun set. There is a dock available for fishing. The cabin is five miles from Tims Ford State Park, eight miles from Jack Daniels Distillery and downtown Lynchburg, eleven miles from Tullahoma, and fifteen miles from Winchester.

May 30 – Jun 6

ﺩ.ﺇ535 per night

Guest favorite

Cottage in Pelham

5.0 out of 5 average rating, 387 reviews

The Milk Barn Cottage

Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about 8 minutes away. Pelham has a coffee shop and quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

Dec 29 – Jan 5

ﺩ.ﺇ578 per night

Superhost

Cabin in Winchester

4.81 out of 5 average rating, 151 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.

Dec 24 – 31

ﺩ.ﺇ564 per night

Superhost

Tiny home in Sewanee

4.86 out of 5 average rating, 207 reviews

¡Mi Cabana! Tiny Home. Big Personality.

¡Mi Cabana! offers THE BEST woodland, tiny home retreat on the mountain. A 10 minute drive will have you visiting all that Sewanee has to offer, only to return to the cozy bosom of the cabin, questioning why you even went out. Built before tiny homes were even cool way back in 2005, and friendly to the planet at every point of its construction, the cabin is 100% pure organic*, gluten free*, and locally sourced Sewanee at its finest. *please do not eat this cabin

Jun 22 – 29

ﺩ.ﺇ320 per night

Guest favorite

Cottage in Hillsboro

4.86 out of 5 average rating, 255 reviews

Eva’s Country Cottage

Our little cottage is halfway between Nashville and Chattanooga. It is only an hour to either city. The Caverns, Bluegrass Underground, is just 15 minutes away. Bonnaroo is just 7 miles up the road and Jack Daniels Distillery and Lynchburg are only 30-45 minutes away. Large lakes and winding rivers are not far away. A quaint older building that was originally built as a church, it was converted into a home in 1964 and has recently been updated and remodeled.

Feb 24 – Mar 3

ﺩ.ﺇ296 per night

Guest favorite

Home in Winchester

5.0 out of 5 average rating, 78 reviews

Historic Home - Walk to Downtown Winchester TN!

Welcome to our beautifully renovated historic home just three blocks from the downtown Winchester square. Walk to see a movie at our historic two-screen theater, grab pizza at Piezan, coffee at Walnut Hill, or dinner and drinks at our new upscale Tavern - Filo's. Of course, we are so close to Tim's Ford Lake and all that has to offer: fishing, boating, water sports. We restored this home from the ground up to create the perfect Airbnb experience.

Oct 21 – 28

ﺩ.ﺇ527 per night

Guest favorite

Cottage in Winchester

4.9 out of 5 average rating, 41 reviews

Peaceful 3 Bedroom Modern Cottage

Relax with the whole family at this peaceful retreat. Conveniently located in Winchester adjacent to Twin Creeks Village. Less than a mile to boat ramp, marina, Drafts and Water Crafts restaurant, Walnut Hill Coffee shop, Piezan Pizzeria, Orange Blossom restaurant, and public beach. Plenty of space for boat parking or rent one at the marina. Less than a half hour to Sewanne/ Monteagle community. Approximately 20 min to Jack Daniels Distillery.

Jul 10 – 17

ﺩ.ﺇ339 per night

Guest favorite

Guesthouse in Tullahoma

4.99 out of 5 average rating, 81 reviews

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!

Oct 3 – 10

ﺩ.ﺇ450 per night

Guest favorite

Barn in Tullahoma

4.97 out of 5 average rating, 124 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.

Sep 16 – 23

ﺩ.ﺇ405 per night

Guest favorite

Guest suite in Manchester

4.98 out of 5 average rating, 349 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.

Oct 22 – 29

ﺩ.ﺇ424 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winchester's top sights

Western Sirloin Steak House9 locals recommend

Holt's Diner6 locals recommend

SUNRISE (The Breakfast Place)16 locals recommend

Las Margaritas6 locals recommend

Kroger14 locals recommend

The Home Depot3 locals recommend

Other great vacation rentals in Winchester

Guest favorite

Tiny home in Tullahoma

5.0 out of 5 average rating, 18 reviews

Whiskey Woods Retreat-Hot Tub

May 31 – Jun 7

ﺩ.ﺇ373 per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 34 reviews

Basecamp Retreat TimsFordLake

Mar 10 – 17

ﺩ.ﺇ881 per night

Guest favorite

Farm stay in Shelbyville

4.98 out of 5 average rating, 65 reviews

Circle C Alpaca Farm - Entire apartment

Jul 27 – Aug 3

ﺩ.ﺇ380 per night

Guest favorite

Cabin in Winchester

5.0 out of 5 average rating, 17 reviews

The Cabins At Rivers Edge

May 24 – 31

ﺩ.ﺇ611 per night

Guest favorite

Home in Decherd

5.0 out of 5 average rating, 59 reviews

Near The Caverns and Sewanee w/ Tesla / EV charger

Feb 14 – 21

ﺩ.ﺇ615 per night

Guest favorite

Home in Winchester

5.0 out of 5 average rating, 17 reviews

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

Nov 27 – Dec 4

ﺩ.ﺇ1,018 per night

Guest favorite

Vacation home in Winchester

4.93 out of 5 average rating, 14 reviews

Lakeside Laurel | Community Pool & Lake Access

Aug 18 – 25

ﺩ.ﺇ742 per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 74 reviews

Beautiful Tim's Ford Lake House (Sleeps 20)

Mar 26 – Apr 2

ﺩ.ﺇ2,632 per night

Show all

Quick stats about vacation rentals in Winchester

Total rentals
120 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees

Frequently Asked Questions

Do cottage rentals in Winchester have free parking?
Absolutely! We offer over 10 cottage 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 $90 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 80 house rentals with a kitchen in Winchester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winchester?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with air conditioning, over 80 homes with a kitchen, over 80 homes with free parking, over 80 homes with wifi, 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 house rentals in Winchester have air conditioning?
Absolutely! We offer over 80 house 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 110 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.

Vacation rentals in Winchester

Top-rated vacation rentals in Winchester

Vacation rentals for every style

Cabins

Houses

Hotels

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Other great vacation rentals in Winchester

Tiny home in Tullahoma

Home in Winchester

Farm stay in Shelbyville

Cabin in Winchester

Home in Decherd

Home in Winchester

Vacation home in Winchester

Home in Winchester

Quick stats about vacation rentals in Winchester

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cottage rentals in Winchester have free parking?

Are there pet-friendly vacation rentals in Winchester?

How much does it cost to stay in cottage rentals in Winchester?

Do house rentals in Winchester have a kitchen?

What are the most popular amenities for House Rentals in Winchester?

Are there Winchester vacation rentals on Airbnb with pools?

Do house rentals in Winchester have air conditioning?

Are there family-friendly vacation rentals in Winchester?

Do cottage rentals in Winchester have wifi?

Are there vacation rentals with a dedicated workspace in Winchester?

Destinations to explore