Vacation rentals in Winchester, TN

98 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Winchester, TN

Beautifully Renovated Studio 2 Miles From Marina! - Winchester, TN

Beautifully Renovated Studio 2 Miles From Marina!

Apartment, Winchester

Beautifully Renovated Studio 2 Miles From Marina! is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Beautifully Renovated Studio 2 Miles From Marina!

Beautifully Renovated Studio 2 Miles From Marina! is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $707.

From$77/night
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Newly Renovated Cozy Place Minutes From The Lake - Winchester, TN

Newly Renovated Cozy Place Minutes From The Lake

Apartment, Winchester

Newly Renovated Cozy Place Minutes From The Lake is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Newly Renovated Cozy Place Minutes From The Lake

Newly Renovated Cozy Place Minutes From The Lake is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $831.

From$91/night
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Renovated Cozy Home Minutes from Tims Ford Lake - Winchester, TN

Renovated Cozy Home Minutes from Tims Ford Lake

Apartment, Winchester

Renovated Cozy Home Minutes from Tims Ford Lake is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Renovated Cozy Home Minutes from Tims Ford Lake

Renovated Cozy Home Minutes from Tims Ford Lake is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $797.

From$114/night
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Beautifully Renovated Studio 2 miles from the Marina - Winchester, TN

Beautifully Renovated Studio 2 miles from the Marina

Apartment, Winchester

Beautifully Renovated Studio 2 miles from the Marina is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Beautifully Renovated Studio 2 miles from the Marina

Beautifully Renovated Studio 2 miles from the Marina is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $798.

From$114/night
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Browse Vacation Rentals with a Pool in Winchester, TN

Add a pool to the search when you want an easy place to cool off between outings.

Tims Ford Lake, Sewanee, and Historic Downtown Winchester - Winchester, TN

Tims Ford Lake, Sewanee, and Historic Downtown Winchester

Holiday Home, Winchester

Tims Ford Lake, Sewanee, and Historic Downtown Winchester is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Tims Ford Lake, Sewanee, and Historic Downtown Winchester

Tims Ford Lake, Sewanee, and Historic Downtown Winchester is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,717.

From$245/night
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Lake Home Retreat w/Lake/Marina Access Golf Cart - Winchester, TN

Lake Home Retreat w/Lake/Marina Access Golf Cart

Holiday Home, Winchester

Lake Home Retreat w/Lake/Marina Access Golf Cart is a holiday home in Winchester, with pool access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Lake Home Retreat w/Lake/Marina Access Golf Cart

Lake Home Retreat w/Lake/Marina Access Golf Cart is a holiday home in Winchester, with pool access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,550.

From$265/night
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Circle E,Lake,Caverns,Sewanee &Jack Daniel’s close by with a jacuzzi waiting - Winchester, TN

Circle E,Lake,Caverns,Sewanee &Jack Daniel’s close by with a jacuzzi waiting

Country House, Winchester

Circle E,Lake,Caverns,Sewanee &Jack Daniel’s close by with a jacuzzi waiting is a country house in Winchester, with pool access and parking. This stay gives travelers a comfortable base for…

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About Circle E,Lake,Caverns,Sewanee &Jack Daniel’s close by with a jacuzzi waiting

Circle E,Lake,Caverns,Sewanee &Jack Daniel’s close by with a jacuzzi waiting is a country house in Winchester, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,115.

From$302/night
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Lake House Dreams in this Fabulous 4-bedroom house in charming Winchester - Winchester, TN

Lake House Dreams in this Fabulous 4-bedroom house in charming Winchester

Holiday Home, Winchester

Lake House Dreams in this Fabulous 4-bedroom house in charming Winchester is a holiday home in Winchester, with pool access and room for a group. This stay gives travelers a comfortable…

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About Lake House Dreams in this Fabulous 4-bedroom house in charming Winchester

Lake House Dreams in this Fabulous 4-bedroom house in charming Winchester is a holiday home in Winchester, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,288.

From$327/night
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Best Winchester, TN vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Guest Suite in Cowan with private entrance: 10 min to University of the South - Winchester, TN

Guest Suite in Cowan with private entrance: 10 min to University of the South

Apartment, Winchester

Guest Suite in Cowan with private entrance: 10 min to University of the South is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the…

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About Guest Suite in Cowan with private entrance: 10 min to University of the South

Guest Suite in Cowan with private entrance: 10 min to University of the South is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $929.

From$133/night
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Tims Ford Lake! Modern farmhouse right across street from State Park - Winchester, TN

Tims Ford Lake! Modern farmhouse right across street from State Park

Country House, Winchester

Tims Ford Lake! Modern farmhouse right across street from State Park is a country house in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Tims Ford Lake! Modern farmhouse right across street from State Park

Tims Ford Lake! Modern farmhouse right across street from State Park is a country house in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,295.

From$185/night
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Cozy4-Bd in Estill Springs 1 min drive to Rock Creek Boat Ramp @ Tims Ford Lake. - Winchester, TN

Cozy4-Bd in Estill Springs 1 min drive to Rock Creek Boat Ramp @ Tims Ford Lake.

Holiday Home, Winchester

Cozy4-Bd in Estill Springs 1 min drive to Rock Creek Boat Ramp @ Tims Ford Lake. is a holiday home in Winchester, with parking and kitchen access. This stay gives travelers a comfortable…

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About Cozy4-Bd in Estill Springs 1 min drive to Rock Creek Boat Ramp @ Tims Ford Lake.

Cozy4-Bd in Estill Springs 1 min drive to Rock Creek Boat Ramp @ Tims Ford Lake. is a holiday home in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,392.

From$199/night
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Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart - Winchester, TN

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

Holiday Home, Winchester

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,171.

From$310/night
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Best Pet-Friendly Vacation Rentals in Winchester, TN

Bring your pet along with stays that welcome four-legged travelers.

Queen ensuite room in historic railroad inn & town. Continental breakfast. - Winchester, TN

Queen ensuite room in historic railroad inn & town. Continental breakfast.

Holiday Home, Winchester

Queen ensuite room in historic railroad inn & town. Continental breakfast. is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Queen ensuite room in historic railroad inn & town. Continental breakfast.

Queen ensuite room in historic railroad inn & town. Continental breakfast. is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $748.

From$107/night
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A very rustic converted pole barn unique cozy cabin - Winchester, TN

A very rustic converted pole barn unique cozy cabin

Cabin, Winchester

A very rustic converted pole barn unique cozy cabin is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $800.

From$114/night
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Near Tims Ford Lake: Peaceful Retreat w/ Patio - Winchester, TN

Near Tims Ford Lake: Peaceful Retreat w/ Patio

Holiday Home, Winchester

Near Tims Ford Lake: Peaceful Retreat w/ Patio is a holiday home in Winchester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Near Tims Ford Lake: Peaceful Retreat w/ Patio

Near Tims Ford Lake: Peaceful Retreat w/ Patio is a holiday home in Winchester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,375.

From$196/night
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Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient! - Winchester, TN

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Holiday Home, Winchester

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient! is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay…

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About Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient! is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,464.

From$209/night
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Best Winchester, TN vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Artsy pet-friendly queen room/historic railroad inn & town. - Winchester, TN

Artsy pet-friendly queen room/historic railroad inn & town.

Holiday Home, Winchester

Artsy pet-friendly queen room/historic railroad inn & town. is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Artsy pet-friendly queen room/historic railroad inn & town.

Artsy pet-friendly queen room/historic railroad inn & town. is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $897.

From$128/night
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1st floor private dog-friendly open plan L/D/K apARTment w/ private Q ensuite BR - Winchester, TN

1st floor private dog-friendly open plan L/D/K apARTment w/ private Q ensuite BR

Holiday Home, Winchester

1st floor private dog-friendly open plan L/D/K apARTment w/ private Q ensuite BR is a holiday home in Winchester, with pet-friendly space, kitchen access, and room for a group. This stay…

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About 1st floor private dog-friendly open plan L/D/K apARTment w/ private Q ensuite BR

1st floor private dog-friendly open plan L/D/K apARTment w/ private Q ensuite BR is a holiday home in Winchester, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,195.

From$171/night
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Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn - Winchester, TN

Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn

Holiday Home, Winchester

Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn

Lake, Caverns, Sewanee, & Jack Daniel’s All Nearby! Boat, RV, Camping, Barn is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,241.

From$320/night
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Shoreside Getaway on Tims Ford Lake w/ Pool Access - Winchester, TN

Shoreside Getaway on Tims Ford Lake w/ Pool Access

Cottage, Winchester

Shoreside Getaway on Tims Ford Lake w/ Pool Access is a cottage in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Shoreside Getaway on Tims Ford Lake w/ Pool Access

Shoreside Getaway on Tims Ford Lake w/ Pool Access is a cottage in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,090.

From$351/night
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Our Favorite Family-Friendly Vacation Rentals in Winchester, TN

Plan a trip with stays that give families more room to spread out.

Tiny Home w/ RV Hookups - Winchester, TN

Tiny Home w/ RV Hookups

Cottage, Winchester

Tiny Home w/ RV Hookups is a cottage in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups is a cottage in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $897.

From$128/night
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Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town. - Winchester, TN

Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town.

Holiday Home, Winchester

Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town. is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town.

Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town. is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $933.

From$133/night
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Near Tims Ford Lake: Peaceful Retreat w/ Patio - Winchester, TN

Near Tims Ford Lake: Peaceful Retreat w/ Patio

Cottage, Winchester

Near Tims Ford Lake: Peaceful Retreat w/ Patio is a cottage in Winchester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Near Tims Ford Lake: Peaceful Retreat w/ Patio

Near Tims Ford Lake: Peaceful Retreat w/ Patio is a cottage in Winchester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,756.

From$190/night
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Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends. - Winchester, TN

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.

Holiday Home, Winchester

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for…

Read more

About Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends. is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,485.

From$212/night
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