Vacation rentals in Chester County, TN

Best vacation rentals and Airbnb offers in Chester County, TN

One Bedroom One Bath Apartment

Apartment, Chester County

One Bedroom One Bath Apartment is a apartment in Chester County, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About One Bedroom One Bath Apartment

One Bedroom One Bath Apartment is a apartment in Chester County, with 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $538.

From$77/night

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The Alexandria House #1

Apartment, Chester County

The Alexandria House #1 is a apartment in Chester County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About The Alexandria House #1

The Alexandria House #1 is a apartment in Chester County. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $657.

From$94/night

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Peaceful Getaway In Charming Tiny House

Holiday Home, Chester County

Peaceful Getaway In Charming Tiny House is a holiday home in Chester County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peaceful Getaway In Charming Tiny House

Peaceful Getaway In Charming Tiny House is a holiday home in Chester County, 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 $681.

From$97/night

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Tiny home cabin by the pond

Cabin, Chester County

Tiny home cabin by the pond is a cabin in Chester County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Tiny home cabin by the pond

Tiny home cabin by the pond is a cabin in Chester County, 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 $686.

From$98/night

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Vacation rentals with a pool in Chester County, TN

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

Cozy 1-bedroom apartment in tranquil Jackson with WiFi, AC, pool

Apartment, Chester County

Cozy 1-bedroom apartment in tranquil Jackson with WiFi, AC, pool is a apartment in Chester County, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 1-bedroom apartment in tranquil Jackson with WiFi, AC, pool

Cozy 1-bedroom apartment in tranquil Jackson with WiFi, AC, pool is a apartment in Chester County, 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,161.

From$166/night

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Guesthouse Rear Suite

Holiday Home, Chester County

Guesthouse Rear Suite is a holiday home in Chester County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guesthouse Rear Suite

Guesthouse Rear Suite is a holiday home in Chester County, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,466.

From$495/night

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Guesthouse Front Suite

Holiday Home, Chester County

Guesthouse Front Suite is a holiday home in Chester County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Guesthouse Front Suite

Guesthouse Front Suite is a holiday home in Chester County, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,074.

From$582/night

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Pet-friendly vacation rentals in Chester County, TN

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

Country Cabin in the Woods

Cabin, Chester County

Country Cabin in the Woods is a cabin in Chester County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Country Cabin in the Woods

Country Cabin in the Woods is a cabin in Chester County, 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 $779.

From$111/night

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2-Bedroom Sweet Retreat in Lexington

Holiday Home, Chester County

2-Bedroom Sweet Retreat in Lexington is a holiday home in Chester County, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About 2-Bedroom Sweet Retreat in Lexington

2-Bedroom Sweet Retreat in Lexington is a holiday home in Chester County, with pet-friendly space, room for a group, 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, hot tub, free wifi, pet friendly, and pets friendly.

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

From$114/night

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Charming 3-bedroom house located in the heart of Jackson.

Holiday Home, Chester County

Charming 3-bedroom house located in the heart of Jackson. is a holiday home in Chester County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 3-bedroom house located in the heart of Jackson.

Charming 3-bedroom house located in the heart of Jackson. is a holiday home in Chester County, 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 $911.

From$130/night

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Vacation rentals with a kitchen in Chester County, TN

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

2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views

Cabin, Chester County

2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views is a cabin in Chester County, with kitchen access and room for a group. This stay gives travelers a…

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About 2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views

2-Bedroom Tiny Home with full kitchen, laundry, wifi, and beautiful pond views is a cabin in Chester County, with 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $875.

From$125/night

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Peaceful 2 Bedroom, 1 bath ~ the Lana Landing ~

Holiday Home, Chester County

Peaceful 2 Bedroom, 1 bath ~ the Lana Landing ~ is a holiday home in Chester County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Peaceful 2 Bedroom, 1 bath ~ the Lana Landing ~

Peaceful 2 Bedroom, 1 bath ~ the Lana Landing ~ is a holiday home in Chester County, 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 $984.

From$141/night

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Highland Manor, King size Beds, Game Room with Treadmill.

Holiday Home, Chester County

Highland Manor, King size Beds, Game Room with Treadmill. is a holiday home in Chester County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Highland Manor, King size Beds, Game Room with Treadmill.

Highland Manor, King size Beds, Game Room with Treadmill. is a holiday home in Chester County, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,049.

From$150/night

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The Perfect Spot #2

Apartment, Chester County

The Perfect Spot #2 is a apartment in Chester County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Perfect Spot #2

The Perfect Spot #2 is a apartment in Chester County, 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 $1,108.

From$158/night

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Family-friendly vacation rentals in Chester County, TN

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

Dog-friendly Jackson Home Near Downtown Hub!

Cottage, Chester County

Dog-friendly Jackson Home Near Downtown Hub! is a cottage in Chester County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Dog-friendly Jackson Home Near Downtown Hub!

Dog-friendly Jackson Home Near Downtown Hub! is a cottage in Chester County, 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 $1,638.

From$169/night

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Covered Patio! Modern Home in Jackson

Cottage, Chester County

Covered Patio! Modern Home in Jackson is a cottage in Chester County, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Covered Patio! Modern Home in Jackson

Covered Patio! Modern Home in Jackson is a cottage in Chester County, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,760.

From$181/night

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Tennessee River Retreat: Multi-level Deck & Views

Cottage, Chester County

Tennessee River Retreat: Multi-level Deck & Views is a cottage in Chester County, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base…

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About Tennessee River Retreat: Multi-level Deck & Views

Tennessee River Retreat: Multi-level Deck & Views is a cottage in Chester County, 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 $2,285.

From$246/night

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Outdoor family time on the patio, at the pool-pool house, or on the boat dock!

Apartment, Chester County

Outdoor family time on the patio, at the pool-pool house, or on the boat dock! is a apartment in Chester County, with pool access, outdoor space, and kitchen access. This stay gives…

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About Outdoor family time on the patio, at the pool-pool house, or on the boat dock!

Outdoor family time on the patio, at the pool-pool house, or on the boat dock! is a apartment in Chester County, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,046.

From$292/night

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