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Winchester Vacation Homes and Villas with Pools

Find Luxury Places to Stay Near Winchester with a Swimming Pool. Find pool in Winchester, Tennessee.

Pool

Only stays with pool access are shown on this page

6 stays

a house with a blue door and a gray at Cozy Lake Cottage W/ Kayaks, SUPs, Pool & Firepit in Winchester

From US $221

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

9.8 (13 Reviews) Holiday_home

The entire place is yours • 142 m² size • Kitchen

Winchester Twin Creeks Marina & Resort • 1.5km from Twin Creeks Marina & Resort

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an aerial view of a row of houses on the water at The Modern Mainstay at Barefoot Bay in Winchester

From US $453

The Modern Mainstay at Barefoot Bay Pool available

9.5 (6 Reviews) Holiday_home

The entire place is yours • 158 m² size • Free on-site parking

Winchester Twin Creeks Marina & Resort • 1.5km from Twin Creeks Marina & Resort

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a white house with a brown roof at Lake Home Retreat w/Lake/Marina Access Golf Cart in Winchester

From US $271

Lake Home Retreat w/Lake/Marina Access Golf Cart Pool available

10.0 (4 Reviews) Holiday_home

The entire place is yours • 278 m² size • Kitchen

Winchester Twin Creeks Marina & Resort • 347m from Twin Creeks Marina & Resort

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a blue house with a garage at Barefoot Retreat in Winchester

From US $229

Barefoot Retreat Pool available

10.0 (3 Reviews) Holiday_home

The entire place is yours • 163 m² size • Free on-site parking

Winchester Twin Creeks Marina & Resort • 1.5km from Twin Creeks Marina & Resort

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a porch with a couch and a view of a field at Tim Ford Lake House in Twin Creeks TN in Winchester

From US $450

Tim Ford Lake House in Twin Creeks TN Pool available

10.0 (3 Reviews) Villa

The entire place is yours • 260 m² size • Free on-site parking

Winchester Twin Creeks Marina & Resort • 673m from Twin Creeks Marina & Resort

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an aerial view of a river with green forests at Luxurious Lake Getaway in Winchester

From US $369

Luxurious Lake Getaway Pool available

10.0 (3 Reviews) Holiday_home

The entire place is yours • 279 m² size • Free on-site parking

Winchester Twin Creeks Marina & Resort • 1.5km from Twin Creeks Marina & Resort

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About Winchester Vacation Rentals with Pools on NearbyHoliday

Looking for pool in Winchester? Compare top options in Tennessee.

Find Winchester Rentals, Hotels, and Resorts with Swimming Pools.

Discover 6 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Winchester that feature indoor, outdoor, or private pools.

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Vacation Rentals with Pools: Explore Top Destinations

Stay Near Winchester's Top Attractions

NearbyHoliday can help you find hotels, resorts, and rentals near many of Winchester's top attractions, neighborhoods, and points of interest. Find pool in Winchester for easier access to nearby attractions.

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Frequently Asked Questions About Vacation Rentals With Pools in Winchester

There are a lot of vacation rentals with pools in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Winchester: