Vacation rentals in Pittsboro, IN

60 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Pittsboro, IN

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! - Pittsboro, IN

5 Mi to Eagle Creek Park: Home w/ Fenced Yard!

Holiday Home, Pittsboro

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! is a holiday home in Pittsboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 5 Mi to Eagle Creek Park: Home w/ Fenced Yard!

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! is a holiday home in Pittsboro, 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 $991.

From$66/night
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Sweet Home in Danville near Speedway Inidanapolis! - Pittsboro, IN

Sweet Home in Danville near Speedway Inidanapolis!

Apartment, Pittsboro

Sweet Home in Danville near Speedway Inidanapolis! is a apartment in Pittsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sweet Home in Danville near Speedway Inidanapolis!

Sweet Home in Danville near Speedway Inidanapolis! is a apartment in Pittsboro, 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 $930.

From$89/night
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Indys Hidden Gem - Pittsboro, IN

Indys Hidden Gem

Homestay, Pittsboro

Indys Hidden Gem is a homestay in Pittsboro, with parking. 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 Indys Hidden Gem

Indys Hidden Gem is a homestay in Pittsboro, 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, for couples, couple massage, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $893.

From$100/night
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Indys Hidden Gem - Pittsboro, IN

Indys Hidden Gem

Homestay, Pittsboro

Indys Hidden Gem is a homestay in Pittsboro, with parking. 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 Indys Hidden Gem

Indys Hidden Gem is a homestay in Pittsboro, 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 $893.

From$100/night
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Browse Vacation Rentals with a Pool in Pittsboro, IN

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

IRIE Living-Cozy Retreat 2BR House with Pool Gym - Pittsboro, IN

IRIE Living-Cozy Retreat 2BR House with Pool Gym

Holiday Home, Pittsboro

IRIE Living-Cozy Retreat 2BR House with Pool Gym is a holiday home in Pittsboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About IRIE Living-Cozy Retreat 2BR House with Pool Gym

IRIE Living-Cozy Retreat 2BR House with Pool Gym is a holiday home in Pittsboro, with pool access, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,174.

From$116/night
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IRIE Living-Haven 2BR Home with Pool Gym Access - Pittsboro, IN

IRIE Living-Haven 2BR Home with Pool Gym Access

Holiday Home, Pittsboro

IRIE Living-Haven 2BR Home with Pool Gym Access is a holiday home in Pittsboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About IRIE Living-Haven 2BR Home with Pool Gym Access

IRIE Living-Haven 2BR Home with Pool Gym Access is a holiday home in Pittsboro, with pool access, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,305.

From$131/night
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IRIE Living-Modern Kg 2Bd Gym Pool, NEW! - Pittsboro, IN

IRIE Living-Modern Kg 2Bd Gym Pool, NEW!

Holiday Home, Pittsboro

IRIE Living-Modern Kg 2Bd Gym Pool, NEW! is a holiday home in Pittsboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About IRIE Living-Modern Kg 2Bd Gym Pool, NEW!

IRIE Living-Modern Kg 2Bd Gym Pool, NEW! is a holiday home in Pittsboro, with pool access, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,386.

From$140/night
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Vintage Danville Retreat | 4BR • Patio • Sleeps 9 - Pittsboro, IN

Vintage Danville Retreat | 4BR • Patio • Sleeps 9

Holiday Home, Pittsboro

Vintage Danville Retreat · 4BR · Patio · Sleeps 9 is a holiday home in Pittsboro, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for…

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About Vintage Danville Retreat | 4BR • Patio • Sleeps 9

Vintage Danville Retreat · 4BR · Patio · Sleeps 9 is a holiday home in Pittsboro, with pet-friendly space, pool access, and outdoor 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,688.

From$196/night
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Best Pittsboro, IN vacation rentals with parking

Find vacation rentals that make arriving by car easier.

New Downtown Apartment | Next to Motor Speedway! - Pittsboro, IN

New Downtown Apartment | Next to Motor Speedway!

Condo, Pittsboro

New Downtown Apartment · Next to Motor Speedway! is a condo in Pittsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About New Downtown Apartment | Next to Motor Speedway!

New Downtown Apartment · Next to Motor Speedway! is a condo in Pittsboro, 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 $988.

From$96/night
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Cozy 3-Bedroom Ranch style house with Huge Backyard & Fire pit - Pittsboro, IN

Cozy 3-Bedroom Ranch style house with Huge Backyard & Fire pit

Holiday Home, Pittsboro

Cozy 3-Bedroom Ranch style house with Huge Backyard & Fire pit is a holiday home in Pittsboro, with parking and room for a group. This stay gives travelers a comfortable base for exploring…

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About Cozy 3-Bedroom Ranch style house with Huge Backyard & Fire pit

Cozy 3-Bedroom Ranch style house with Huge Backyard & Fire pit is a holiday home in Pittsboro, with parking 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,052.

From$111/night
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Modern King Bed | Relax & Stay - Pittsboro, IN

Modern King Bed | Relax & Stay

Apartment, Pittsboro

Modern King Bed · Relax & Stay is a apartment in Pittsboro, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Modern King Bed | Relax & Stay

Modern King Bed · Relax & Stay is a apartment in Pittsboro, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,112.

From$122/night
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Refined Comforts: Luxe Stay in Whitestown Indiana - Pittsboro, IN

Refined Comforts: Luxe Stay in Whitestown Indiana

Apartment, Pittsboro

Refined Comforts: Luxe Stay in Whitestown Indiana is a apartment in Pittsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Refined Comforts: Luxe Stay in Whitestown Indiana

Refined Comforts: Luxe Stay in Whitestown Indiana is a apartment in Pittsboro, 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 $1,069.

From$123/night
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Best Pet-Friendly Vacation Rentals in Pittsboro, IN

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

Clean Spacious Home | 3 Bedrooms | Close to Airport - Pittsboro, IN

Clean Spacious Home | 3 Bedrooms | Close to Airport

Holiday Home, Pittsboro

Clean Spacious Home · 3 Bedrooms · Close to Airport is a holiday home in Pittsboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Clean Spacious Home | 3 Bedrooms | Close to Airport

Clean Spacious Home · 3 Bedrooms · Close to Airport is a holiday home in Pittsboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,180.

From$104/night
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Illustrious Suite Spacious 2BR 2BA 2 King Beds WFH - Pittsboro, IN

Illustrious Suite Spacious 2BR 2BA 2 King Beds WFH

Apartment, Pittsboro

Illustrious Suite Spacious 2BR 2BA 2 King Beds WFH is a apartment in Pittsboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Illustrious Suite Spacious 2BR 2BA 2 King Beds WFH

Illustrious Suite Spacious 2BR 2BA 2 King Beds WFH is a apartment in Pittsboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,270.

From$122/night
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20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym - Pittsboro, IN

20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

Apartment, Pittsboro

20 mins DT · Sleeps 9 · Sunrise Glow Spacious Gym is a apartment in Pittsboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About 20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

20 mins DT · Sleeps 9 · Sunrise Glow Spacious Gym is a apartment in Pittsboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,321.

From$130/night
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Decadent Haven Spacious 2BR 2BA King Beds WFH GYM - Pittsboro, IN

Decadent Haven Spacious 2BR 2BA King Beds WFH GYM

Apartment, Pittsboro

Decadent Haven Spacious 2BR 2BA King Beds WFH GYM is a apartment in Pittsboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Decadent Haven Spacious 2BR 2BA King Beds WFH GYM

Decadent Haven Spacious 2BR 2BA King Beds WFH GYM is a apartment in Pittsboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,333.

From$132/night
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Best Pittsboro, IN vacation rentals with a kitchen

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

Speedway Casa Verde: Convenient location to IMS, Indy attractions and hospitals. - Pittsboro, IN

Speedway Casa Verde: Convenient location to IMS, Indy attractions and hospitals.

Holiday Home, Pittsboro

Speedway Casa Verde: Convenient location to IMS, Indy attractions and hospitals. is a holiday home in Pittsboro, with parking and kitchen access. This stay gives travelers a comfortable…

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About Speedway Casa Verde: Convenient location to IMS, Indy attractions and hospitals.

Speedway Casa Verde: Convenient location to IMS, Indy attractions and hospitals. is a holiday home in Pittsboro, 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 $1,285.

From$130/night
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Modern, marble-accented studio for comfort - Pittsboro, IN

Modern, marble-accented studio for comfort

Apartment, Pittsboro

Modern, marble-accented studio for comfort is a apartment in Pittsboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Modern, marble-accented studio for comfort

Modern, marble-accented studio for comfort is a apartment in Pittsboro, 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 $1,221.

From$136/night
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Fabulous 4 Bed /2.5 Bath - Near Speedway, Sleeps 8 - Pittsboro, IN

Fabulous 4 Bed /2.5 Bath - Near Speedway, Sleeps 8

Holiday Home, Pittsboro

Fabulous 4 Bed /2.5 Bath - Near Speedway, Sleeps 8 is a holiday home in Pittsboro, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Fabulous 4 Bed /2.5 Bath - Near Speedway, Sleeps 8

Fabulous 4 Bed /2.5 Bath - Near Speedway, Sleeps 8 is a holiday home in Pittsboro, with parking, 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 parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,396.

From$141/night
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4 Mi to Dtwn: Danville Home w/ Patio & Yard - Pittsboro, IN

4 Mi to Dtwn: Danville Home w/ Patio & Yard

Holiday Home, Pittsboro

4 Mi to Dtwn: Danville Home w/ Patio & Yard is a holiday home in Pittsboro, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 4 Mi to Dtwn: Danville Home w/ Patio & Yard

4 Mi to Dtwn: Danville Home w/ Patio & Yard is a holiday home in Pittsboro, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,055.

From$176/night
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Our Favorite Family-Friendly Vacation Rentals in Pittsboro, IN

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

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! - Pittsboro, IN

5 Mi to Eagle Creek Park: Home w/ Fenced Yard!

Cottage, Pittsboro

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! is a cottage in Pittsboro, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 5 Mi to Eagle Creek Park: Home w/ Fenced Yard!

5 Mi to Eagle Creek Park: Home w/ Fenced Yard! is a cottage in Pittsboro, 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 $1,051.

From$109/night
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8 Mi to Dtwn Indianapolis: Family Home w/ Yard! - Pittsboro, IN

8 Mi to Dtwn Indianapolis: Family Home w/ Yard!

Holiday Home, Pittsboro

8 Mi to Dtwn Indianapolis: Family Home w/ Yard! is a holiday home in Pittsboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 8 Mi to Dtwn Indianapolis: Family Home w/ Yard!

8 Mi to Dtwn Indianapolis: Family Home w/ Yard! is a holiday home in Pittsboro, 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 $1,596.

From$138/night
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Kid Friendly 2 Bedroom Home with Washer & Dryer - Pittsboro, IN

Kid Friendly 2 Bedroom Home with Washer & Dryer

Holiday Home, Pittsboro

Kid Friendly 2 Bedroom Home with Washer & Dryer is a holiday home in Pittsboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Kid Friendly 2 Bedroom Home with Washer & Dryer

Kid Friendly 2 Bedroom Home with Washer & Dryer is a holiday home in Pittsboro, 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 $1,369.

From$139/night
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4 Mi to Dtwn: Danville Home w/ Patio & Yard - Pittsboro, IN

4 Mi to Dtwn: Danville Home w/ Patio & Yard

Cottage, Pittsboro

4 Mi to Dtwn: Danville Home w/ Patio & Yard is a cottage in Pittsboro, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 4 Mi to Dtwn: Danville Home w/ Patio & Yard

4 Mi to Dtwn: Danville Home w/ Patio & Yard is a cottage in Pittsboro, 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 $2,089.

From$225/night
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