Middleburg Holiday House Rentals from AU$243: Search Holiday Homes

Middleburg Holiday Homes
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Our top choices for Middleburg holiday homes

A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view through a glass door.

A living room with a fireplace, a beige armchair, and a black ottoman.

A covered porch with stone flooring, two chairs, a rug, and a glass door with a black frame.

A modern living room with a dining area, large windows, and a sofa with a red cushion.

1. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm

Middleburg

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"

Denise B.

The price is AU$827

AU$827

includes taxes & fees

5 Oct - 6 Oct

Spacious Modern Home on Middleburg Horse Farm

A two-story house with a porch, surrounded by trees and grass.

A living room with a sofa, TV, fireplace, and large windows.

A porch with wooden rocking chairs, a potted plant, a doormat, and a ceiling fan.

An American flag hanging from a porch, surrounded by greenery and trees.

2. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"We love this house. It was super quiet and cozy. The kitchen is the best stocked Vrbo kitchen we have ever encountered. If there is a drawback, I would say that it is the antique/original doorknobs. They do need to be repaired or replaced for ease of use. But on the other hand, no biggie and kind of add to the charm. We thoroughly enjoyed our stay!"

Mark H.

The price is AU$526

AU$526

includes taxes & fees

24 Sept - 25 Sept

1910 Farmhouse on 6 Acres • VA Wine Country

3. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres

Loudoun County

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a great stay. House is beautiful and clean and owner was highly responsive. "

Michele B.

The price is AU$635

AU$635

includes taxes & fees

29 Sept - 30 Sept

DC Wine Country Farmhouse | 5 Peaceful Acres

A modern living room with a sofa, yellow chairs, a dining table, and a TV mounted on the wall.

A small, single-story house with a front porch, a small garden, and a tree.

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a patterned rug.

A bedroom with a wooden bed, white bedding, a ceiling fan, bedside lamps, a small stool, and a window with blinds.

4. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard

Leesburg

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Clean sweet place to stay and relax. Couldn't have been nicer."

Avis V.

The price is AU$445

AU$445

includes taxes & fees

27 Sept - 28 Sept

Leesburg Hideaway- King Bed + Private Backyard

A hot tub in a forested area with a rocky ground and trees.

A modern kitchen with white cabinets, a stainless steel refrigerator, and an oven.

A living room with a blue sofa, a coffee table, and artwork on the wall.

A bedroom with a bed, a ceiling fan, two windows, a nightstand, a lamp, and a painting.

5. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub

Harpers Ferry

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "

Brett D.

The price is AU$510

AU$510

includes taxes & fees

24 Sept - 25 Sept

The Blue Jay | New House in the Woods w/ Hot Tub

A single-story house with a porch, a swing, and an American flag.

A house with a porch, a flag, and a swing set.

6. Charming Cottage, Walk to Downtown, Porch Swings

Charming Cottage, Walk to Downtown, Porch Swings

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"it was a clean house and quite area. perfect!"

John S.

The price is AU$534

AU$534

includes taxes & fees

30 Sept - 1 Oct

Charming Cottage, Walk to Downtown, Porch Swings

A deck with outdoor seating and a lake view.

A garden with a stone pathway, surrounded by various plants and trees.

A spacious living area with wooden flooring, a dining table, chairs, a coffee table, and a ceiling fan.

A spacious kitchen with wooden flooring, a dining area with a wooden table and chairs, and a stone accent wall.

7. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Harpers Ferry

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "

Liz P.

The price is AU$383

AU$383

includes taxes & fees

28 Sept - 29 Sept

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

A modern kitchen with a large island, bar stools, pendant lighting, and a view of the outside through a window.

A house with a stone staircase leading to a wooden deck.

A house with a stone staircase leading to a door, a small patio with a table and two chairs, and flower boxes on the windowsills.

A modern kitchen with white cabinets, a central island, and hanging pendant lights. There are three bar stools and a round woven ottoman in the dining area.

8. Retreat in Historic Downtown Leesburg - Walkable to Everything!

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Leesburg's Old and Historic District

9.8 out of 10, Exceptional, (28 reviews)

9.8/10

Exceptional

(28 reviews)

"Excellent location and nice little house."

Ann B.

The price is AU$654

AU$654

includes taxes & fees

24 Sept - 25 Sept

Retreat in Historic Downtown Leesburg - Walkable to Everything!

A bedroom with a large bed, two bedside lamps, a potted plant, and a small ottoman.

A living room with a brick fireplace, a television displaying 'NETFLIX', two armchairs, a small table with a lace tablecloth, and decorative items.

A two-story house with a brick foundation, a front door with a black trim, and a small front yard with a tree and shrubs.

A living room with a brick fireplace, a television mounted above it, and a coffee table with a remote control.

9. Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.

Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.

Sterling

9.8 out of 10, Exceptional, (120 reviews)

9.8/10

Exceptional

(120 reviews)

"We had a quick stay but it was perfect for what we needed. "

Deana B.

The price is AU$243

AU$243

includes taxes & fees

5 Oct - 6 Oct

Comfortable. Spacious. Quiet. 3 miles from Dulles Airport.

A large estate with multiple buildings, expansive outdoor seating areas, and surrounding vineyards.

A yellow house with a porch, a front door, and two windows.

A spacious living room with a sofa, armchair, and a coffee table. There is a wooden dresser, a lamp, and a television.

A room with a wooden dresser, a mirror, a vase with flowers, a chair, and a window with blinds.

10. Storybook cottage on Leesburg's most historic block — walk to everything

Storybook cottage on Leesburg's most historic block — walk to everything

Leesburg's Old and Historic District

9.6 out of 10, Exceptional, (76 reviews)

9.6/10

Exceptional

(76 reviews)

"Spotless and super comfortable—exactly what we needed. We loved our quick weekend getaway here. The location is fantastic, just steps from downtown Leesburg’s charming shops, restaurants, and everything else. Highly recommend!"

draje7

The price is AU$646

AU$646

includes taxes & fees

19 Oct - 20 Oct

Storybook cottage on Leesburg's most historic block — walk to everything

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a sofa and coffee tables.

A bedroom with bunk beds, a desk, a chair, a lamp, and a patterned rug.

A kitchen with white cabinets, a microwave, a coffee maker, a sink, and a window.

A narrow hallway with a wooden floor, white walls, and a skylight.

11. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Front Royal

The price is AU$574

AU$574

includes taxes & fees

29 Sept - 30 Sept

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

A backyard with a fire pit surrounded by Adirondack chairs, a wooden deck, and string lights.

A bedroom with a bed, a window with blinds, a door leading to a bathroom, and a shower area.

A modern kitchen with white cabinetry, a stainless steel oven, a microwave, and a red toaster.

A backyard with a fire pit, Adirondack chairs, and a wooden deck.

12. Downtown Cottage with Fire Pit

Downtown Cottage with Fire Pit

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Delightful cottage, super convenient, and our host was extremely nice and attentive. "

Mark M.

The price is AU$716

AU$716

includes taxes & fees

19 Oct - 20 Oct

Downtown Cottage with Fire Pit

A spacious dining area with a wooden table and chairs, large windows with a view of trees, and a stone wall in the background.

A dining area with a wooden table, green chairs, and a white cabinet with glass doors.

A spacious living room with a stone fireplace, wooden ceiling beams, large windows, and a modern entertainment unit.

An aerial view of a house with a large deck, surrounded by trees and a dry landscape.

13. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub

Harpers Ferry

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Beautiful scenery! Beautiful home! Wonderful hosts!"

Brian S.

The price is AU$557

AU$557

includes taxes & fees

6 Oct - 7 Oct

Stone Cabin on Valley View: Fire Pit + Hot Tub

A hot tub under a wooden pergola with a view of autumn trees.

A dining area with a long table set for a meal, a hanging light fixture, and a sofa in the background.

A two-story cabin with a balcony, surrounded by trees with autumn foliage.

A living room with a fireplace, a sofa, a chair, a coffee table, and a TV mounted on the wall.

14. Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Harpers Ferry

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"We had a great stay "

Lauren O.

The price is AU$752

AU$752

includes taxes & fees

27 Sept - 28 Sept

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

A spacious living room with a green sofa set, a coffee table, and a fireplace. There is a kitchen in the background with a large window overlooking a deck.

A modern living room with two leather chairs, a small table, a rug, and a large window with a view of trees.

A modern living room with a sofa, coffee table, and TV. There is a dining area with chairs and a table in the background.

A modern kitchen with white cabinets, stainless steel appliances, and a view of the outdoors.

15. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Harpers Ferry

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We loved it! So peaceful and beautiful property. Andrea is a great host!"

Erin C.

The price is AU$559

AU$559

includes taxes & fees

28 Sept - 29 Sept

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, and a window providing natural light.

A modern living room with a flat-screen TV, a unique wooden coffee table, a gray sofa, and a colorful cow painting.

A bedroom with two beds, white headboards, and a window with blinds.

A modern living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a flat-screen TV mounted on the wall.

16. Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Well appointed and very walkable to nearby downtown."

Sean S.

The price is AU$731

AU$731

includes taxes & fees

22 Oct - 23 Oct

Quaint Royal Cottage @ Historic Leesburg

A modern living room with a sectional sofa, a coffee table, a fireplace, and a large flat-screen TV mounted on the wall.

A bathroom with a white sink, a mirror with a gold frame, and a light fixture above the mirror.

A backyard with a red shed, a brick wall, and a tree.

A floor plan of a modern apartment with a living area, dining space, kitchen, and a staircase.

17. Downtown Retreat with 2 Primary Suites

Downtown Retreat with 2 Primary Suites

Leesburg

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very clean, larger unit than expected. Very comfortable and close to many shops and restaurants. Would highly recommend! We had a wonderful stay."

Tyler W.

The price is AU$566

AU$566

includes taxes & fees

4 Oct - 5 Oct

Downtown Retreat with 2 Primary Suites

A bar area with wooden beams, hanging light fixtures, and a bar counter with stools.

A bedroom with a bed, bedside tables, a chair, a dresser, and a window with curtains.

A dining area with a wooden ceiling, a kitchen with blue cabinets, and a tiled floor.

A sign for Walsh Family Wine Tasting Room with a wooden fence and greenery in the background.

18. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything

Purcellville

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"The property was great! Very clean and walkable to town. We had a wonderful time and Joe was great to work with! We would absolutely love to stay here again!"

melissa b.

The price is AU$1,103

AU$1,103

includes taxes & fees

29 Sept - 30 Sept

Main Street USA -- Walk to Everything

A wooden deck with a view of a forested landscape and a sunset.

A living room with a wooden floor, a sofa, a coffee table with board games, books, and a gaming console. There is a TV and speakers in the background.

An aerial view of a house surrounded by dense forest, with a clear sky above.

19. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Harpers Ferry

9.0 out of 10, Wonderful, (14 reviews)

9.0/10

Wonderful

(14 reviews)

"House was clean and loaded with required amenities. We loved the backyard view and the proximity to the lakeside picnic area."

henu m.

The price is AU$535

AU$535

includes taxes & fees

28 Sept - 29 Sept

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A sign for Antietam National Battlefield, part of the National Park Service, with a stone wall and flowers in the foreground.

A covered patio with a brick wall, a glass table, and blue chairs.

A neatly made bed with a quilt, pillows, and a bedside table with a lamp.

A living room with a sofa, coffee table, and a TV stand.

20. Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Harpers Ferry

7.4 out of 10, Good, (28 reviews)

7.4/10

Good

(28 reviews)

"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."

Melissa H.

The price is AU$489

AU$489

includes taxes & fees

13 Oct - 14 Oct

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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