Middleburg Holiday Homes from €87: Search Top House Rentals

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

A house with a garage, a chimney, and a lawn.

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

1. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm

Middleburg

10.0 out of 10, Exceptional, (20 reviews)

10/10

Exceptional

(20 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 €530

€530

includes taxes & fees

5 Oct - 6 Oct

Spacious Modern Home on Middleburg Horse Farm

2. DC Wine Country Farmhouse | 5 Peaceful Acres

DC Wine Country Farmhouse | 5 Peaceful Acres

Loudoun County

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

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

Michele B.

The price is €402

€402

includes taxes & fees

28 Sept - 29 Sept

DC Wine Country Farmhouse | 5 Peaceful Acres

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.

A dining area with a wooden table, white chairs, a chandelier, and large windows with views of greenery.

3. 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 €350

€350

includes taxes & fees

5 Oct - 6 Oct

1910 Farmhouse on 6 Acres • VA Wine Country

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

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

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.

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 €288

€288

includes taxes & fees

4 Oct - 5 Oct

Leesburg Hideaway- King Bed + Private Backyard

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

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

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

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

A deck with outdoor seating and a lake view.

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

A beach with two empty lounge chairs facing a calm lake, surrounded by a chain-link fence and a dock in the background.

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

6. 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

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 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 €203

€203

includes taxes & fees

13 Sept - 14 Sept

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

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

A wooden dresser with a mirror, a vase with flowers, and books.

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

A spacious cafe with a marble counter, wooden tables, and large windows offering a view of the outdoors.

7. 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, (73 reviews)

9.6/10

Exceptional

(73 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 €327

€327

includes taxes & fees

9 Sept - 10 Sept

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

A wooden deck with two Adirondack chairs and a small table, two wine glasses on the table, surrounded by lush green trees.

A hallway with a wooden door featuring a stained glass window, a wall with large red and blue letters, and a light switch on the wall.

A modern kitchen with wooden cabinets, a built-in oven, and a stainless steel refrigerator.

A two-story house with a porch and a staircase leading to the entrance.

8. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

Harpers Ferry

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "

Maeve K.

The price is €372

€372

includes taxes & fees

22 Sept - 23 Sept

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 €151

€151

includes taxes & fees

13 Sept - 14 Sept

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

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 wooden cabin with a deck, outdoor seating, and a covered area.

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

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

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Front Royal

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

A sectional sofa with a storage ottoman, a large potted plant, and a lamp.

A wooden console table with a lamp, a potted plant, and a notebook.

A laundry room with a sink, two washing machines, and a countertop with storage containers.

A modern kitchen with white cabinets, a granite countertop, stainless steel appliances, and a built-in oven.

11. Stylish Studio with Kitchenette

Stylish Studio with Kitchenette

Sterling

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very organized and had tons of quality of life features."

Hunter J.

The price is €180

€180

includes taxes & fees

22 Sept - 23 Sept

Stylish Studio with Kitchenette

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

A covered porch with white chairs and a table, large windows offering a view of greenery.

12. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom

Front Royal

9.0 out of 10, Wonderful, (32 reviews)

9.0/10

Wonderful

(32 reviews)

"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "

Elissa S.

The price is €265

€265

includes taxes & fees

8 Sept - 9 Sept

Mountain home w/ hot tub & sunroom

A modern kitchen with stainless steel appliances, grey cabinetry, and a black rug.

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

A modern kitchen with a dining area, wooden flooring, and a view of the outdoors.

13. 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.

Charming Cottage, Walk to Downtown, Porch Swings

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

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.

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

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

14. Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Well appointed and very walkable to nearby downtown."

Sean S.

The price is €436

€436

includes taxes & fees

9 Sept - 10 Sept

Quaint Royal Cottage @ Historic Leesburg

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

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

A stone-walled room with a fireplace, a sofa, and a wooden floor.

15. 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 €331

€331

includes taxes & fees

22 Sept - 23 Sept

Stone Cabin on Valley View: Fire Pit + Hot Tub

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

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

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

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

16. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything

Purcellville

9.6 out of 10, Exceptional, (8 reviews)

9.6/10

Exceptional

(8 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 €678

€678

includes taxes & fees

13 Sept - 14 Sept

Main Street USA -- Walk to Everything

A kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

A modern living room with a sectional sofa, a fireplace, and a large mirror.

A bedroom with a four-poster bed, a flat-screen TV, a wooden dresser, and a walk-in closet.

A modern dining area with a round table, white upholstered chairs, and a black vase with dried plants.

17. Renovated 3B/3B Home | Downtown | Private Fire Pit

Renovated 3B/3B Home | Downtown | Private Fire Pit

Leesburg's Old and Historic District

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

Exceptional

(42 reviews)

"Great location, would stay again."

Eric D S.

Renovated 3B/3B Home | Downtown | Private Fire Pit

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

A room with a door leading to a balcony, a mirror on the wall, and a welcome mat at the entrance.

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.

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

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"Excellent location and nice little house."

Ann B.

The price is €457

€457

includes taxes & fees

9 Sept - 10 Sept

Retreat in Historic Downtown Leesburg - Walkable to Everything!

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

A living room with a brown sofa, a grey armchair, a glass coffee table, and a patterned rug.

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.

19. The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home

Leesburg's Old and Historic District

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

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

Mark M.

The Cottage on Royal - Historic Leesburg Home

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

A large, modern house with a balcony, surrounded by a forest and rocky terrain.

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

20. 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)

"Welcoming host, great place!"

Amanda M.

The price is €336

€336

includes taxes & fees

8 Sept - 9 Sept

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

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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Top Middleburg Hotel Reviews

The Westin Washington Dulles Airport

10/10 Excellent

"Enjoyed my stay at the Westin Dulles. Was there for an event. The hotel was very nice, the staff were very friendly, and the event was enjoyable."

John 2-night trip

Posted 5 hours ago

The Westin Washington Dulles Airport

Embassy Suites by Hilton Dulles Airport

8/10 Good

"Breakfast, clean room, hot tub and staff."

Denise 1-night trip

Posted 8 hours ago

Embassy Suites by Hilton Dulles Airport

DoubleTree by Hilton Washington Dulles Airport

10/10 Excellent

"Missed our connecting flight and had to stay near IAD overnight. Nice property, gave us late checkout and helpful staff. Highly recommend."

Donald 1-night trip

Posted 11 hours ago

DoubleTree by Hilton Washington Dulles Airport

Holiday Inn Washington-Dulles International Airport by IHG

10/10 Excellent

"Great stay"

Alexandre 1-night trip

Posted 11 hours ago

Holiday Inn Washington-Dulles International Airport by IHG

Comfort Suites Manassas Battlefield Park

8/10 Good

"House keeper came in 2 hours before check out while we were asleep kinda nerve racking waking up to lol but good experience over all"

Brooke 1-night trip

Posted 1 day ago

Comfort Suites Manassas Battlefield Park

Lansdowne Resort and Spa

10/10 Excellent

"A lovely place to spend a weekend. Staff was helpful and friendly. Everything was great"

Donald 1-night trip

Posted 2 days ago

Lansdowne Resort and Spa

Courtyard by Marriott Dulles Airport Herndon

10/10 Excellent

"Location and access to numerous attractions in the area."

Cheri 1-night trip

Posted 2 days ago

Courtyard by Marriott Dulles Airport Herndon

Holiday Inn Chantilly - Dulles Arpt Area by IHG

10/10 Excellent

"The rooms were very clean. The staff was very friendly, especially Kiarah that works at the restaurant. The Airport shuttle took an hour to pick me up after I called and said I was ready for pick up."

Pamela 1-night trip

Posted 5 days ago

Holiday Inn Chantilly - Dulles Arpt Area by IHG

The Red Fox Inn & Tavern

10/10 Excellent

"The delivery of the delicious breakfast and pot of perfect coffee was my favorite!"

Audra 5-night trip

Posted 9 days ago

The Red Fox Inn & Tavern

Find out more about Middleburg

Middleburg Holiday Homes information

Number of reviews	3,413
Accommodation	290 Holiday Homes
Lowest Price	€87
Highest Price	€760

Holiday Homes in Middleburg

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middleburg holiday homes

1. Spacious Modern Home on Middleburg Horse Farm

2. DC Wine Country Farmhouse | 5 Peaceful Acres

3. 1910 Farmhouse on 6 Acres • VA Wine Country

4. Leesburg Hideaway- King Bed + Private Backyard

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

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

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

8. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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

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

11. Stylish Studio with Kitchenette

12. Mountain home w/ hot tub & sunroom

13. Charming Cottage, Walk to Downtown, Porch Swings

14. Quaint Royal Cottage @ Historic Leesburg

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

16. Main Street USA -- Walk to Everything

17. Renovated 3B/3B Home | Downtown | Private Fire Pit

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

19. The Cottage on Royal - Historic Leesburg Home

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

Find holiday rentals that suit your style

Top Middleburg Hotel Reviews

The Westin Washington Dulles Airport

Find out more about Middleburg

Middleburg Holiday Homes information