Vacation rentals in Philomont, VA

58 available vacation rental offers

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Best vacation rentals and Airbnb offers in Philomont, VA

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. - Philomont, VA

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Apartment, Philomont

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. is a apartment in Philomont, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. is a apartment in Philomont, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$173/night
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6 Mi to Historic Leesburg: Apt w/ On-site Dining - Philomont, VA

6 Mi to Historic Leesburg: Apt w/ On-site Dining

Apartment, Philomont

6 Mi to Historic Leesburg: Apt w/ On-site Dining is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 6 Mi to Historic Leesburg: Apt w/ On-site Dining

6 Mi to Historic Leesburg: Apt w/ On-site Dining is a apartment in Philomont, 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 $1,550.

From$175/night
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Gastropub On-site: Loudoun Wine Country Apartment - Philomont, VA

Gastropub On-site: Loudoun Wine Country Apartment

Apartment, Philomont

Gastropub On-site: Loudoun Wine Country Apartment is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Gastropub On-site: Loudoun Wine Country Apartment

Gastropub On-site: Loudoun Wine Country Apartment is a apartment in Philomont, 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 $1,550.

From$175/night
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Near Loudoun Wine Trail: Apt w/ Restaurant On-site - Philomont, VA

Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Apartment, Philomont

Near Loudoun Wine Trail: Apt w/ Restaurant On-site is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Near Loudoun Wine Trail: Apt w/ Restaurant On-site is a apartment in Philomont, 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 $1,550.

From$175/night
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Vacation rentals with a pool in Philomont, VA

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

Shiloh, Shiloh Renovated Farm House in Purcellville - Philomont, VA

Shiloh, Shiloh Renovated Farm House in Purcellville

Holiday Home, Philomont

Shiloh, Shiloh Renovated Farm House in Purcellville is a holiday home in Philomont, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Shiloh, Shiloh Renovated Farm House in Purcellville

Shiloh, Shiloh Renovated Farm House in Purcellville is a holiday home in Philomont, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,565.

From$795/night
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2 minutes to the Upperville Horse Show - Philomont, VA

2 minutes to the Upperville Horse Show

Holiday Home, Philomont

2 minutes to the Upperville Horse Show is a holiday home in Philomont, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 minutes to the Upperville Horse Show

2 minutes to the Upperville Horse Show is a holiday home in Philomont, 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 $8,497.

From$1,214/night
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Luxury Villa w/ Private Pool & Game Lounge Charming 3-bedroom and private pool - Philomont, VA

Luxury Villa w/ Private Pool & Game Lounge Charming 3-bedroom and private pool

Holiday Home, Philomont

Luxury Villa w/ Private Pool & Game Lounge Charming 3-bedroom and private pool is a holiday home in Philomont, with pool access and room for a group. This stay gives travelers a comfortable…

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About Luxury Villa w/ Private Pool & Game Lounge Charming 3-bedroom and private pool

Luxury Villa w/ Private Pool & Game Lounge Charming 3-bedroom and private pool is a holiday home in Philomont, 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,496.

From$1,357/night
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Inn at Evergreen - Philomont, VA

Inn at Evergreen

B & B, Philomont

Inn at Evergreen is a b & b in Philomont, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Evergreen

Inn at Evergreen is a b & b in Philomont, 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 breakfast, pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,652.

From$332/night
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Vacation rentals with parking in Philomont, VA

Find vacation rentals that make arriving by car easier.

6 Mi to Historic Leesburg: Apt w/ On-Site Dining - Philomont, VA

6 Mi to Historic Leesburg: Apt w/ On-Site Dining

Apartment, Philomont

6 Mi to Historic Leesburg: Apt w/ On-Site Dining is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 6 Mi to Historic Leesburg: Apt w/ On-Site Dining

6 Mi to Historic Leesburg: Apt w/ On-Site Dining is a apartment in Philomont, 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 $1,231.

From$176/night
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Gastropub On-Site: Loudoun Wine Country Apartment - Philomont, VA

Gastropub On-Site: Loudoun Wine Country Apartment

Apartment, Philomont

Gastropub On-Site: Loudoun Wine Country Apartment is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Gastropub On-Site: Loudoun Wine Country Apartment

Gastropub On-Site: Loudoun Wine Country Apartment is a apartment in Philomont, 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 $1,231.

From$176/night
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Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues - Philomont, VA

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

Apartment, Philomont

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues is a apartment in Philomont, 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 $1,544.

From$221/night
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Historic Farmhouse, Fully Renovated in Fall 2023 - Philomont, VA

Historic Farmhouse, Fully Renovated in Fall 2023

Country House, Philomont

Historic Farmhouse, Fully Renovated in Fall 2023 is a country house in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Historic Farmhouse, Fully Renovated in Fall 2023

Historic Farmhouse, Fully Renovated in Fall 2023 is a country house in Philomont, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,734.

From$391/night
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Pet-friendly vacation rentals in Philomont, VA

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

Harpers Ferry Cabin - Walk to Private Lake! - Philomont, VA

Harpers Ferry Cabin - Walk to Private Lake!

Holiday Home, Philomont

Harpers Ferry Cabin - Walk to Private Lake! is a holiday home in Philomont, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Harpers Ferry Cabin - Walk to Private Lake!

Harpers Ferry Cabin - Walk to Private Lake! is a holiday home in Philomont, 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 $1,570.

From$140/night
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Harpers Ferry Cabin - Walk to Private Lake! - Philomont, VA

Harpers Ferry Cabin - Walk to Private Lake!

Cabin, Philomont

Harpers Ferry Cabin - Walk to Private Lake! is a cabin in Philomont, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Harpers Ferry Cabin - Walk to Private Lake!

Harpers Ferry Cabin - Walk to Private Lake! is a cabin in Philomont, 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 $1,377.

From$197/night
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Magical Log Cabin w/Fireplace/ 15 min to Harpers - Philomont, VA

Magical Log Cabin w/Fireplace/ 15 min to Harpers

Cabin, Philomont

Magical Log Cabin w/Fireplace/ 15 min to Harpers is a cabin in Philomont, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Magical Log Cabin w/Fireplace/ 15 min to Harpers

Magical Log Cabin w/Fireplace/ 15 min to Harpers is a cabin in Philomont, 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 $1,492.

From$213/night
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Lamontagne Farmhouse a Rural Pristine Setting - Philomont, VA

Lamontagne Farmhouse a Rural Pristine Setting

Holiday Home, Philomont

Lamontagne Farmhouse a Rural Pristine Setting is a holiday home in Philomont, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lamontagne Farmhouse a Rural Pristine Setting

Lamontagne Farmhouse a Rural Pristine Setting is a holiday home in Philomont, 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 $2,824.

From$403/night
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Vacation rentals with a kitchen in Philomont, VA

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

Near Loudoun Wine Trail: Apt w/ Restaurant On-Site - Philomont, VA

Near Loudoun Wine Trail: Apt w/ Restaurant On-Site

Apartment, Philomont

Near Loudoun Wine Trail: Apt w/ Restaurant On-Site is a apartment in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Near Loudoun Wine Trail: Apt w/ Restaurant On-Site

Near Loudoun Wine Trail: Apt w/ Restaurant On-Site is a apartment in Philomont, 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 $1,231.

From$176/night
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Charming, Cozy, Mountain Cabin in the Woods<br> - Philomont, VA

Charming, Cozy, Mountain Cabin in the Woods<br>

Cabin, Philomont

Charming, Cozy, Mountain Cabin in the Woods<br> is a cabin in Philomont, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming, Cozy, Mountain Cabin in the Woods<br>

Charming, Cozy, Mountain Cabin in the Woods<br> is a cabin in Philomont, 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 $1,495.

From$214/night
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The Serenity Cabin | Firepit | Wineries | Hiking - Philomont, VA

The Serenity Cabin | Firepit | Wineries | Hiking

Cabin, Philomont

The Serenity Cabin · Firepit · Wineries · Hiking is a cabin in Philomont, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Serenity Cabin | Firepit | Wineries | Hiking

The Serenity Cabin · Firepit · Wineries · Hiking is a cabin in Philomont, 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 $1,534.

From$219/night
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Historic home nestled in the heart of horse and wine country. Kids/pet friendly! - Philomont, VA

Historic home nestled in the heart of horse and wine country. Kids/pet friendly!

Holiday Home, Philomont

Historic home nestled in the heart of horse and wine country. Kids/pet friendly! is a holiday home in Philomont, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Historic home nestled in the heart of horse and wine country. Kids/pet friendly!

Historic home nestled in the heart of horse and wine country. Kids/pet friendly! is a holiday home in Philomont, 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 $2,287.

From$327/night
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Family-friendly vacation rentals in Philomont, VA

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

Harpers Ferry Cabin - Walk to Private Lake! - Philomont, VA

Harpers Ferry Cabin - Walk to Private Lake!

Cottage, Philomont

Harpers Ferry Cabin - Walk to Private Lake! is a cottage in Philomont, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Harpers Ferry Cabin - Walk to Private Lake!

Harpers Ferry Cabin - Walk to Private Lake! is a cottage in Philomont, 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 $1,542.

From$173/night
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Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area - Philomont, VA

Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area

Cottage, Philomont

Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area is a cottage in Philomont, with a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area

Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area is a cottage in Philomont, with 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,308.

From$187/night
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A Restored Wagon Barn On A 1790's Farm. - Philomont, VA

A Restored Wagon Barn On A 1790's Farm.

Cottage, Philomont

A Restored Wagon Barn On A 1790's Farm. is a cottage in Philomont, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A Restored Wagon Barn On A 1790's Farm.

A Restored Wagon Barn On A 1790's Farm. is a cottage in Philomont, 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 $1,600.

From$229/night
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Lovely Guest House 2.5 miles from downtown Middleburg - Philomont, VA

Lovely Guest House 2.5 miles from downtown Middleburg

Cottage, Philomont

Lovely Guest House 2.5 miles from downtown Middleburg is a cottage in Philomont, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lovely Guest House 2.5 miles from downtown Middleburg

Lovely Guest House 2.5 miles from downtown Middleburg is a cottage in Philomont, 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 $2,412.

From$345/night
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