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Leesburg Holiday Apartments

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50 rentals in Leesburg.
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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 4
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Vineyard View Lodge, holiday rental in Leesburg
Vineyard View Lodge, holiday rental in Leesburg
Vineyard View Lodge, holiday rental in Leesburg

Vineyard View Lodge

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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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'Thomson Farm' Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg
'Thomson Farm' Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg
'Thomson Farm' Classic Home < 10 Mi to Vineyards!, holiday rental in Leesburg

'Thomson Farm' Classic Home < 10 Mi to Vineyards!

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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1920s Historic Bungalow Luxury Finishes Cozy Charm, holiday rental in Leesburg
1920s Historic Bungalow Luxury Finishes Cozy Charm, holiday rental in Leesburg
1920s Historic Bungalow Luxury Finishes Cozy Charm, holiday rental in Leesburg

1920s Historic Bungalow Luxury Finishes Cozy Charm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Huge home in Leesburg, holiday rental in Leesburg
Huge home in Leesburg, holiday rental in Leesburg
Huge home in Leesburg, holiday rental in Leesburg

Huge home in Leesburg

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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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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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
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Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, holiday rental in Leesburg
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, holiday rental in Leesburg
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, holiday rental in Leesburg

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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 6
Match: Sleeps
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Country Cottage on 1700’s Horse Farm/Wedding Venue, holiday rental in Leesburg
Country Cottage on 1700’s Horse Farm/Wedding Venue, holiday rental in Leesburg
Country Cottage on 1700’s Horse Farm/Wedding Venue, holiday rental in Leesburg

Country Cottage on 1700’s Horse Farm/Wedding Venue

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Leesburg
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Leesburg
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Leesburg

Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Guest House at 1796 Historic Plantation Farm in Wine Country, holiday rental in Leesburg
Guest House at 1796 Historic Plantation Farm in Wine Country, holiday rental in Leesburg
Guest House at 1796 Historic Plantation Farm in Wine Country, holiday rental in Leesburg

Guest House at 1796 Historic Plantation Farm in Wine Country

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lux 5BD + Private Theatre, Gym, Game Room, Parking, holiday rental in Leesburg
Lux 5BD + Private Theatre, Gym, Game Room, Parking, holiday rental in Leesburg
Lux 5BD + Private Theatre, Gym, Game Room, Parking, holiday rental in Leesburg

Lux 5BD + Private Theatre, Gym, Game Room, Parking

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi  ***ASK FOR NEW YEAR'S QUOTE***, holiday rental in Leesburg
Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi  ***ASK FOR NEW YEAR'S QUOTE***, holiday rental in Leesburg
Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi  ***ASK FOR NEW YEAR'S QUOTE***, holiday rental in Leesburg

Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi ***ASK FOR NEW YEAR'S QUOTE***

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, holiday rental in Leesburg
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, holiday rental in Leesburg
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, holiday rental in Leesburg

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Middleburg Home with 4 Bedrooms and 2 Full Baths, holiday rental in Leesburg
Luxury Middleburg Home with 4 Bedrooms and 2 Full Baths, holiday rental in Leesburg
Luxury Middleburg Home with 4 Bedrooms and 2 Full Baths, holiday rental in Leesburg

Luxury Middleburg Home with 4 Bedrooms and 2 Full Baths

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Paradise in Horse Country, holiday rental in Leesburg
Paradise in Horse Country, holiday rental in Leesburg
Paradise in Horse Country, holiday rental in Leesburg

Paradise in Horse Country

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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Spacious One Bedroom Apartment With Private Entrance, holiday rental in Leesburg
Spacious One Bedroom Apartment With Private Entrance, holiday rental in Leesburg
Spacious One Bedroom Apartment With Private Entrance, holiday rental in Leesburg

Spacious One Bedroom Apartment With Private Entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Your Best Stay! Cozy Abode on the Potomac River, holiday rental in Leesburg
Your Best Stay! Cozy Abode on the Potomac River, holiday rental in Leesburg
Your Best Stay! Cozy Abode on the Potomac River, holiday rental in Leesburg

Your Best Stay! Cozy Abode on the Potomac River

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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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
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The Van Gogh Room in Villa, holiday rental in Leesburg
The Van Gogh Room in Villa, holiday rental in Leesburg
The Van Gogh Room in Villa, holiday rental in Leesburg

The Van Gogh Room in Villa

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
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Modern Farmhouse Getaway, holiday rental in Leesburg
Modern Farmhouse Getaway, holiday rental in Leesburg
Modern Farmhouse Getaway, holiday rental in Leesburg

Modern Farmhouse Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Country Home With 3 Plus Bedrooms, holiday rental in Leesburg
Private Country Home With 3 Plus Bedrooms, holiday rental in Leesburg
Private Country Home With 3 Plus Bedrooms, holiday rental in Leesburg

Private Country Home With 3 Plus Bedrooms

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Leesburg
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Leesburg
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Leesburg

Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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
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Sterling Townhome - Private & Santized, in a Quiet & Safe neighborhood. Self che, holiday rental in Leesburg
Sterling Townhome - Private & Santized, in a Quiet & Safe neighborhood. Self che, holiday rental in Leesburg
Sterling Townhome - Private & Santized, in a Quiet & Safe neighborhood. Self che, holiday rental in Leesburg

Sterling Townhome - Private & Santized, in a Quiet & Safe neighborhood. Self che

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hunt Box on 1700's Horse Farm/Wedding Venue, holiday rental in Leesburg
Hunt Box on 1700's Horse Farm/Wedding Venue, holiday rental in Leesburg
Hunt Box on 1700's Horse Farm/Wedding Venue, holiday rental in Leesburg

Hunt Box on 1700's Horse Farm/Wedding Venue

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
2 bathrooms
Sleeps 6
Match: Sleeps
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Hidden View - All 5-Suites, holiday rental in Leesburg
Hidden View - All 5-Suites, holiday rental in Leesburg
Hidden View - All 5-Suites, holiday rental in Leesburg

Hidden View - All 5-Suites

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, holiday rental in Leesburg
Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, holiday rental in Leesburg
Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, holiday rental in Leesburg

Your own amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool

Holiday Rental House
9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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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
1 bathroom
Sleeps 3
Match: Sleeps
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French Farm house /Apartment., holiday rental in Leesburg
French Farm house /Apartment., holiday rental in Leesburg
French Farm house /Apartment., holiday rental in Leesburg

French Farm house /Apartment.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Catoctin Valley Country Home, holiday rental in Leesburg
Catoctin Valley Country Home, holiday rental in Leesburg
Catoctin Valley Country Home, holiday rental in Leesburg

Catoctin Valley Country Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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Corporate Housing/Relocation/LongTermStay-60D, holiday rental in Leesburg
Corporate Housing/Relocation/LongTermStay-60D, holiday rental in Leesburg
Corporate Housing/Relocation/LongTermStay-60D, holiday rental in Leesburg

Corporate Housing/Relocation/LongTermStay-60D

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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“Virginian retreat” (15 minutes from IAD Airport ), holiday rental in Leesburg
“Virginian retreat” (15 minutes from IAD Airport ), holiday rental in Leesburg
“Virginian retreat” (15 minutes from IAD Airport ), holiday rental in Leesburg

“Virginian retreat” (15 minutes from IAD Airport )

Holiday Rental House
1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
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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
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Top Rated Townhome - Our reviews say it all. Large discount during pandemic. Sel, holiday rental in Leesburg
Top Rated Townhome - Our reviews say it all. Large discount during pandemic. Sel, holiday rental in Leesburg
Top Rated Townhome - Our reviews say it all. Large discount during pandemic. Sel, holiday rental in Leesburg

Top Rated Townhome - Our reviews say it all. Large discount during pandemic. Sel

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
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Corporate Housing/Relocation.LongTermStay/30D, holiday rental in Leesburg
Corporate Housing/Relocation.LongTermStay/30D, holiday rental in Leesburg
Corporate Housing/Relocation.LongTermStay/30D, holiday rental in Leesburg

Corporate Housing/Relocation.LongTermStay/30D

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Couple's romantic getaway. Minutes from IAD airport( Short term stays only), holiday rental in Leesburg
Couple's romantic getaway. Minutes from IAD airport( Short term stays only), holiday rental in Leesburg
Couple's romantic getaway. Minutes from IAD airport( Short term stays only), holiday rental in Leesburg

Couple's romantic getaway. Minutes from IAD airport( Short term stays only)

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxury Townhome - Largest Corner unit with Patio, Deck, basement, and all new lu, holiday rental in Leesburg
Luxury Townhome - Largest Corner unit with Patio, Deck, basement, and all new lu, holiday rental in Leesburg
Luxury Townhome - Largest Corner unit with Patio, Deck, basement, and all new lu, holiday rental in Leesburg

Luxury Townhome - Largest Corner unit with Patio, Deck, basement, and all new lu

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Farm View Cottage With Pond, holiday rental in Leesburg
Farm View Cottage With Pond, holiday rental in Leesburg
Farm View Cottage With Pond, holiday rental in Leesburg

Farm View Cottage With Pond

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Townhome Hosted by Super Host! Private & Sanitized, Self checkin. Long stays wel, holiday rental in Leesburg
Townhome Hosted by Super Host! Private & Sanitized, Self checkin. Long stays wel, holiday rental in Leesburg
Townhome Hosted by Super Host! Private & Sanitized, Self checkin. Long stays wel, holiday rental in Leesburg

Townhome Hosted by Super Host! Private & Sanitized, Self checkin. Long stays wel

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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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
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Ste Gannon Way

Hosted by Newman Hospitality - Sprightly - Remote worker paradis, holiday rental in Leesburg
Ste Gannon Way

Hosted by Newman Hospitality - Sprightly - Remote worker paradis, holiday rental in Leesburg
Ste Gannon Way

Hosted by Newman Hospitality - Sprightly - Remote worker paradis, holiday rental in Leesburg

Ste Gannon Way Hosted by Newman Hospitality - Sprightly - Remote worker paradis

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
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