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Holiday Rentals in Leesburg

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50 rentals in Leesburg.
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Tentrr Signature Site - Nut Orchard Retreat, holiday rental in Leesburg
Tentrr Signature Site - Nut Orchard Retreat, holiday rental in Leesburg
Tentrr Signature Site - Nut Orchard Retreat, holiday rental in Leesburg

Tentrr Signature Site - Nut Orchard Retreat

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage on King St | Historic Charm | Modern Living, holiday rental in Leesburg
Cottage on King St | Historic Charm | Modern Living, holiday rental in Leesburg
Cottage on King St | Historic Charm | Modern Living, holiday rental in Leesburg

Cottage on King St | Historic Charm | Modern Living

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Country Living | 10 acres | Views!, holiday rental in Leesburg
Luxury Country Living | 10 acres | Views!, holiday rental in Leesburg
Luxury Country Living | 10 acres | Views!, holiday rental in Leesburg

Luxury Country Living | 10 acres | Views!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues, holiday rental in Leesburg
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues, holiday rental in Leesburg
Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues, holiday rental in Leesburg

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg, holiday rental in Leesburg
East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg, holiday rental in Leesburg
East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg, holiday rental in Leesburg

East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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The PINK PEARL in Historic Leesburg, holiday rental in Leesburg
The PINK PEARL in Historic Leesburg, holiday rental in Leesburg
The PINK PEARL in Historic Leesburg, holiday rental in Leesburg

The PINK PEARL in Historic Leesburg

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic and Updated Farmhouse Built in 1808, holiday rental in Leesburg
Historic and Updated Farmhouse Built in 1808, holiday rental in Leesburg
Historic and Updated Farmhouse Built in 1808, holiday rental in Leesburg

Historic and Updated Farmhouse Built in 1808

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Cottage on Royal - Historic Leesburg Home, holiday rental in Leesburg
The Cottage on Royal - Historic Leesburg Home, holiday rental in Leesburg
The Cottage on Royal - Historic Leesburg Home, holiday rental in Leesburg

The Cottage on Royal - Historic Leesburg Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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WINDRIDGE = Romantic, Fun, Log House; Close to Historic Sites, Wineries & Shops, holiday rental in Leesburg
WINDRIDGE = Romantic, Fun, Log House; Close to Historic Sites, Wineries & Shops, holiday rental in Leesburg
WINDRIDGE = Romantic, Fun, Log House; Close to Historic Sites, Wineries & Shops, holiday rental in Leesburg

WINDRIDGE = Romantic, Fun, Log House; Close to Historic Sites, Wineries & Shops

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Large Nice Home in Leesburg, holiday rental in Leesburg
Large Nice Home in Leesburg, holiday rental in Leesburg
Large Nice Home in Leesburg, holiday rental in Leesburg

Large Nice Home in Leesburg

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Secluded Leesburg Retreat w/ Private Hot Tub!, holiday rental in Leesburg
NEW! Secluded Leesburg Retreat w/ Private Hot Tub!, holiday rental in Leesburg
NEW! Secluded Leesburg Retreat w/ Private Hot Tub!, holiday rental in Leesburg

NEW! Secluded Leesburg Retreat w/ Private Hot Tub!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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&#39;Thomson Farm&#39; Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg
&#39;Thomson Farm&#39; Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg
&#39;Thomson Farm&#39; Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg

&#39;Thomson Farm&#39; Classic Home < 10 Mi to Vineyards!

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
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Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia, holiday rental in Leesburg
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia, holiday rental in Leesburg
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia, holiday rental in Leesburg

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
More info
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Charming Cottage convenient to Leesburg.  Wineries, Hiking and more., holiday rental in Leesburg
Charming Cottage convenient to Leesburg.  Wineries, Hiking and more., holiday rental in Leesburg
Charming Cottage convenient to Leesburg.  Wineries, Hiking and more., holiday rental in Leesburg

Charming Cottage convenient to Leesburg. Wineries, Hiking and more.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Vineyard View *M&M Farm, holiday rental in Leesburg
The Vineyard View *M&M Farm, holiday rental in Leesburg
The Vineyard View *M&M Farm, holiday rental in Leesburg

The Vineyard View *M&M Farm

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Karens Cottage, holiday rental in Leesburg
Karens Cottage, holiday rental in Leesburg
Karens Cottage, holiday rental in Leesburg

Karens Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Waterford Cottage King The Village, holiday rental in Leesburg
Waterford Cottage King The Village, holiday rental in Leesburg
Waterford Cottage King The Village, holiday rental in Leesburg

Waterford Cottage King The Village

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Waterford Reservations Guest Cottage, holiday rental in Leesburg
Waterford Reservations Guest Cottage, holiday rental in Leesburg
Waterford Reservations Guest Cottage, holiday rental in Leesburg

Waterford Reservations Guest Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Privacy on 3 gorgeous acres, holiday rental in Leesburg
Privacy on 3 gorgeous acres, holiday rental in Leesburg
Privacy on 3 gorgeous acres, holiday rental in Leesburg

Privacy on 3 gorgeous acres

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Peaceful Waterford Farmhouse in a Bucolic Setting, holiday rental in Leesburg
Peaceful Waterford Farmhouse in a Bucolic Setting, holiday rental in Leesburg
Peaceful Waterford Farmhouse in a Bucolic Setting, holiday rental in Leesburg

Peaceful Waterford Farmhouse in a Bucolic Setting

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Take a Walk Around The Lake - Close to many attractions and Airport., holiday rental in Leesburg
Take a Walk Around The Lake - Close to many attractions and Airport., holiday rental in Leesburg
Take a Walk Around The Lake - Close to many attractions and Airport., holiday rental in Leesburg

Take a Walk Around The Lake - Close to many attractions and Airport.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming Schoolhouse Retreat, holiday rental in Leesburg
Charming Schoolhouse Retreat, holiday rental in Leesburg
Charming Schoolhouse Retreat, holiday rental in Leesburg

Charming Schoolhouse Retreat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Romantic Stone Cottage Circa 1869-75 acres to Hike, holiday rental in Leesburg
Romantic Stone Cottage Circa 1869-75 acres to Hike, holiday rental in Leesburg
Romantic Stone Cottage Circa 1869-75 acres to Hike, holiday rental in Leesburg

Romantic Stone Cottage Circa 1869-75 acres to Hike

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Don Rea Luxury Villa, holiday rental in Leesburg
Don Rea Luxury Villa, holiday rental in Leesburg
Don Rea Luxury Villa, holiday rental in Leesburg

Don Rea Luxury Villa

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Restored 1820 Waterford Village Farmhouse, holiday rental in Leesburg
Restored 1820 Waterford Village Farmhouse, holiday rental in Leesburg
Restored 1820 Waterford Village Farmhouse, holiday rental in Leesburg

Restored 1820 Waterford Village Farmhouse

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Cottage at Oakland Green Farm, holiday rental in Leesburg
The Cottage at Oakland Green Farm, holiday rental in Leesburg
The Cottage at Oakland Green Farm, holiday rental in Leesburg

The Cottage at Oakland Green Farm

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Couple's romantic getaway, holiday rental in Leesburg
Couple's romantic getaway, holiday rental in Leesburg
Couple's romantic getaway, holiday rental in Leesburg

Couple's romantic getaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Relaxing, Comfy, Pet Friendly 2/2 Apartment w/ Gym, holiday rental in Leesburg
Relaxing, Comfy, Pet Friendly 2/2 Apartment w/ Gym, holiday rental in Leesburg
Relaxing, Comfy, Pet Friendly 2/2 Apartment w/ Gym, holiday rental in Leesburg

Relaxing, Comfy, Pet Friendly 2/2 Apartment w/ Gym

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Historic Waterford House -  King Bed Walk To Winery, holiday rental in Leesburg
Historic Waterford House -  King Bed Walk To Winery, holiday rental in Leesburg
Historic Waterford House -  King Bed Walk To Winery, holiday rental in Leesburg

Historic Waterford House - King Bed Walk To Winery

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Sheraton Vistiana , holiday rental in Leesburg
Sheraton Vistiana , holiday rental in Leesburg
Sheraton Vistiana , holiday rental in Leesburg

Sheraton Vistiana

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Cottage at Twin Notch Farm, holiday rental in Leesburg
The Cottage at Twin Notch Farm, holiday rental in Leesburg
The Cottage at Twin Notch Farm, holiday rental in Leesburg

The Cottage at Twin Notch Farm

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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A unique mountaintop getaway overlooking Willow Croft Winery across the street, holiday rental in Leesburg
A unique mountaintop getaway overlooking Willow Croft Winery across the street, holiday rental in Leesburg
A unique mountaintop getaway overlooking Willow Croft Winery across the street, holiday rental in Leesburg

A unique mountaintop getaway overlooking Willow Croft Winery across the street

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, holiday rental in Leesburg
Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, holiday rental in Leesburg
Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, holiday rental in Leesburg

Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Luxury End Unit Townhome Just 40 Minutes from DC, Pet-Friendly, Privacy Fenced, holiday rental in Leesburg
Luxury End Unit Townhome Just 40 Minutes from DC, Pet-Friendly, Privacy Fenced, holiday rental in Leesburg
Luxury End Unit Townhome Just 40 Minutes from DC, Pet-Friendly, Privacy Fenced, holiday rental in Leesburg

Luxury End Unit Townhome Just 40 Minutes from DC, Pet-Friendly, Privacy Fenced

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Leesburg Spacious Home, holiday rental in Leesburg
Leesburg Spacious Home, holiday rental in Leesburg
Leesburg Spacious Home, holiday rental in Leesburg

Leesburg Spacious Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Country Cottage nestled in Wine Country, holiday rental in Leesburg
Modern Country Cottage nestled in Wine Country, holiday rental in Leesburg
Modern Country Cottage nestled in Wine Country, holiday rental in Leesburg

Modern Country Cottage nestled in Wine Country

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Purcellville Near Leesburg Harpers Ferry Wineries, holiday rental in Leesburg
Purcellville Near Leesburg Harpers Ferry Wineries, holiday rental in Leesburg
Purcellville Near Leesburg Harpers Ferry Wineries, holiday rental in Leesburg

Purcellville Near Leesburg Harpers Ferry Wineries

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Laurel Hill Farm, private Pre-Revolution Farmhouse in Virginia Wine Country, holiday rental in Leesburg
Laurel Hill Farm, private Pre-Revolution Farmhouse in Virginia Wine Country, holiday rental in Leesburg
Laurel Hill Farm, private Pre-Revolution Farmhouse in Virginia Wine Country, holiday rental in Leesburg

Laurel Hill Farm, private Pre-Revolution Farmhouse in Virginia Wine Country

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Tall Oaks Cabin, Walk to Wineries and Breweries!, holiday rental in Leesburg
Tall Oaks Cabin, Walk to Wineries and Breweries!, holiday rental in Leesburg
Tall Oaks Cabin, Walk to Wineries and Breweries!, holiday rental in Leesburg

Tall Oaks Cabin, Walk to Wineries and Breweries!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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3BR TH 40 Mins from DC, Pets OK, Fenced Yard, holiday rental in Leesburg
3BR TH 40 Mins from DC, Pets OK, Fenced Yard, holiday rental in Leesburg
3BR TH 40 Mins from DC, Pets OK, Fenced Yard, holiday rental in Leesburg

3BR TH 40 Mins from DC, Pets OK, Fenced Yard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Leesburg 26-acre Farm IAD/12mi Wine/11mi *** ASK FOR X-MAS QUOTE ***, holiday rental in Leesburg
Leesburg 26-acre Farm IAD/12mi Wine/11mi *** ASK FOR X-MAS QUOTE ***, holiday rental in Leesburg
Leesburg 26-acre Farm IAD/12mi Wine/11mi *** ASK FOR X-MAS QUOTE ***, holiday rental in Leesburg

Leesburg 26-acre Farm IAD/12mi Wine/11mi *** ASK FOR X-MAS QUOTE ***

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Rare 5BR/3.5BA Townhome in No VA, Family Community, Pet Friendly, Fast WiFi, holiday rental in Leesburg
Rare 5BR/3.5BA Townhome in No VA, Family Community, Pet Friendly, Fast WiFi, holiday rental in Leesburg
Rare 5BR/3.5BA Townhome in No VA, Family Community, Pet Friendly, Fast WiFi, holiday rental in Leesburg

Rare 5BR/3.5BA Townhome in No VA, Family Community, Pet Friendly, Fast WiFi

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg
Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg
Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg

Lux 5BD - Theater, Gym, Game Room, Parking & more!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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Gorgeous, Wooded 3 Acre Estate -5 Bed/4  Bath-Leesburg/Brambleton/Aldie area, holiday rental in Leesburg
Gorgeous, Wooded 3 Acre Estate -5 Bed/4  Bath-Leesburg/Brambleton/Aldie area, holiday rental in Leesburg
Gorgeous, Wooded 3 Acre Estate -5 Bed/4  Bath-Leesburg/Brambleton/Aldie area, holiday rental in Leesburg

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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4 Bdr. Suburban Home | Near D.C, Perfect for Families, 24 Hr. Pro Host Support, holiday rental in Leesburg
4 Bdr. Suburban Home | Near D.C, Perfect for Families, 24 Hr. Pro Host Support, holiday rental in Leesburg
4 Bdr. Suburban Home | Near D.C, Perfect for Families, 24 Hr. Pro Host Support, holiday rental in Leesburg

4 Bdr. Suburban Home | Near D.C, Perfect for Families, 24 Hr. Pro Host Support

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg
Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg
Lux 5BD - Theater, Gym, Game Room, Parking & more!, holiday rental in Leesburg

Lux 5BD - Theater, Gym, Game Room, Parking & more!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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Lovely Single Family 3-bedroom townhouse ~ Quiet neighborhood, holiday rental in Leesburg
Lovely Single Family 3-bedroom townhouse ~ Quiet neighborhood, holiday rental in Leesburg
Lovely Single Family 3-bedroom townhouse ~ Quiet neighborhood, holiday rental in Leesburg

Lovely Single Family 3-bedroom townhouse ~ Quiet neighborhood

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Trinity Farm Estate: Magnolia 1775 Historical Farmhouse, holiday rental in Leesburg
Trinity Farm Estate: Magnolia 1775 Historical Farmhouse, holiday rental in Leesburg
Trinity Farm Estate: Magnolia 1775 Historical Farmhouse, holiday rental in Leesburg

Trinity Farm Estate: Magnolia 1775 Historical Farmhouse

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Bluebell Overlook with firepit, holiday rental in Leesburg
Bluebell Overlook with firepit, holiday rental in Leesburg
Bluebell Overlook with firepit, holiday rental in Leesburg

Bluebell Overlook with firepit

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Trinity Farm Manor: Private Lake Retreat and Soccer Arena, holiday rental in Leesburg
Trinity Farm Manor: Private Lake Retreat and Soccer Arena, holiday rental in Leesburg
Trinity Farm Manor: Private Lake Retreat and Soccer Arena, holiday rental in Leesburg

Trinity Farm Manor: Private Lake Retreat and Soccer Arena

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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