Entire home

Charming Writer's Cottage in the Heart of Middleburg

Photo gallery for Charming Writer's Cottage in the Heart of Middleburg

A small, green wooden structure with a sloped roof and two windows with shutters.
A living room with a sofa, armchairs, a coffee table, and lamps. There are framed pictures on the walls and a window with blinds.
A bedroom with a bed, two bedside tables, a lamp, a bookshelf, and a window with curtains.
A dining area with a round wooden table, chairs, a vase with flowers, a bookshelf, and a staircase.
A white building with black shutters, a red door, and a black metal archway.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Middleburg Historic District
1 bedroom1+ bathroomSleeps 2

Popular amenities

  • Patio
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Internet
  • Washing machine

Explore the area

View map
Middleburg, VA
  • Place, Middleburg Historic District
    ‪6 min walk‬
  • Place, Red Fox Fine Art
    ‪6 min walk‬
  • Place, The Byrne Gallery
    ‪6 min walk‬
  • Airport, Washington, DC (IAD-Washington Dulles Intl.)
    ‪34 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom, 1 half bathroom

Bathroom 1

Toilet · Shower only · Hair dryer

Bathroom 2

Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

About this property

Charming Writer's Cottage in the Heart of Middleburg

Come and stay, be inspired, write a best seller or spend a cozy weekend shopping and dining in the heart of Virginia horse country.

From this fully updated 1820 historic home that was once the dormitory for the original Middleburg Academy, you can walk to many fine restaurants, and enjoy premier shopping and antiques. The only known fully permitted historic vacation property actually in the Old Town of Middleburg!
The downstairs features a nicely appointed furnished living room that includes cable television, comfortable seating, with an adjoining half bath; a stately tavern room that disguises a home office with full internet access and a working Royal Deluxe typewriter that Ernest Hemingway would surely envy; and an eat-in kitchen with all necessary cooking items, adjoining a door to the deck and spacious back yard.
Note that although this historic cottage has two front doors, it is a single family home - the doors likely being a vestige of its dormitory origin.

The upstairs features a large bedroom with a very comfortable Queen-sized bed adjoining an over-sized full bath with a walk-in shower. This home is ready for you to enjoy - stay a while - use the typewriter!! Begin the story . . . . .

1 Bedroom, 1.5 Baths, Eat In country kitchen, Dining area Hard Wood Floors, Great home office area, washer/dryer, large back yard, off street parking, Cable and High Speed internet.
Pets accepted with deposit on a case by case basis.

Please note that the price listed by this site of $259+ per night is only an average based upon taking into consideration the weekly and monthly rate discounts. The price per day based upon rentals for under a week is a reasonable $255 before taxes and VRBO fees.

Add dates for prices

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
Well Behaved Pets are allowed upon approval.
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Smoking

Smoking is not permitted
The Golden Rule - Respect the property and leave it like you found it.

Important information

You need to know

Property # 4040604
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Middleburg

Middleburg is home to this cottage. The Boxwood Winery and Greenhill Winery & Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Bull Run Mountains State Natural Area and Sky Meadows State Park. Looking to enjoy an event or a game while in town? See what's happening at Purcellville Skating Rink or Haymarket IcePlex. Take the opportunity to explore the area for outdoor excitement like horse riding and other activities like birdwatching.
View more Cottages in MiddleburgOpens in a new window
Map
Middleburg, VA

What's nearby

  • Middleburg Historic District - 6 min walk - 0.6 km
  • Red Fox Fine Art - 6 min walk - 0.6 km
  • The Byrne Gallery - 6 min walk - 0.6 km
  • Museum of Hounds & Hunting North America - 6 min walk - 0.6 km
  • Middleburg Community Center - 9 min walk - 0.8 km

Getting around

  • Washington Dulles International Airport (IAD) - 35 min drive

Restaurants

  • ‪Red Horse Tavern - ‬9 min walk
  • ‪The Red Fox Inn & Tavern - ‬6 min walk
  • ‪Boxwood Estate Winery - ‬4 min drive
  • ‪Lost Barrel Brewing - ‬4 min drive
  • ‪Middleburg Common Grounds - ‬8 min walk

Frequently asked questions

Is Charming Writer's Cottage in the Heart of Middleburg pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at Charming Writer's Cottage in the Heart of Middleburg?

As of 4 Oct 2026, prices found for a 1-night stay for 2 adults at Charming Writer's Cottage in the Heart of Middleburg on 27 Oct 2026 start from AU$975, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming Writer's Cottage in the Heart of Middleburg?

On-site parking is available at the property.

What time is check-in at Charming Writer's Cottage in the Heart of Middleburg?

Check-in begins at 3:00 PM.

What time is check-out at Charming Writer's Cottage in the Heart of Middleburg?

Checkout is at 11:00 AM.

Where is Charming Writer's Cottage in the Heart of Middleburg located?

Situated in Middleburg, this cottage is within a 10-minute walk of Red Fox Fine Art, Middleburg Historic District and The Byrne Gallery. Museum of Hounds & Hunting North America and Middleburg Community Center are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 156 out of 174 reviews
Rating 8 - Good. 13 out of 174 reviews
Rating 6 - Okay. 4 out of 174 reviews
Rating 4 - Poor. 0 out of 174 reviews
Rating 2 - Terrible. 1 out of 174 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It’s a very cool space with awesome location.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The history and the location of the cottage made this the perfect spot for a Middleburg stay.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location to everything!
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a lovely charming place to stay in Middleburg. It was such an easy walk to town. You never needed to get into your car. Great restaurants, nearby and great shopping. Michael was very attentive and there if you need him.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The best part about this house is its location! You can walk to all the shops and restaurants downtown with ease.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about my stay was perfect!! Michael the host was amazing with his timely responses. We Highly recommend this place if your coming to middleburg.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming and conveniently located.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, host, and house!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay. Cozy and convenient to everything Middleburg had to offer. Host was very friendly and responsive.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent place! Great host with good communication.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was absolutely adorable. Very clean. Michael was so easy to work with and always available for any communication we needed. We would definitely stay here again.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming place in walking distance to town. Perfect for a weekend getaway. The home is well-appointed with everything you could need and the host is super kind and responsive. Will stay again!
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location, very cute cottage
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice little cottage walking distance from everything in Middleburg. Would definitely stay again!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We can’t say enough wonderful things about Michael and his beautiful home in Middleburg! The location was perfection - walking distance to central downtown allowed us to really make the most of our time. There’s ample private parking, the house was adorable and very comfortable, and Michael was so kind and helpful. He’s a great communicator and gave us such a warm welcome! Thank you for the wonderful stay, Michael! The house made our weekend unforgettable and we’ll absolutely be back!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely charming cottage with so many thoughtful details. I just loved it. Great location -in walking distance to town. And the owners were responsive.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, cozy, lovely cottage. Friendly and accommodating host. Great location.
Stayed 2 nights in Nov 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home with a lot of historic charm located with walking distance to the Main Street of Middleburg. Perfect spot for our short stay. Home is also well equipped and cozy!
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay in Middleburg

The house is in a great location and Michael was a fantastic host. Would definitely stay there again
Stayed 2 nights in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This charming historic property is ideally located in order to enjoy the Christmas Parade in Middleburg. We loved staying here and the house was perfect for us. The owner was great with getting us in and settled. We couldn’t have asked for a better experience.
Stayed 2 nights in Dec 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kitchen was well stocked
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great cottage good location

Walking distance to everything Cottage comfortable, clean and well stocked
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay in Middleburg! The house looked just like the photos, and Michael was extremely nice and communicative before our arrival. This location can't be beat. Perfect for a couple with a dog to stay and enjoy a long weekend.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Michael is great and very responsive. The location is wonderful for activities in and around Middleburg.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is perfectly located to walk the downtown which oozes charm.Michael was an excellent host with the best communication we have experienced with VRBO.Would highly recommend to anyone wishing to experience Middleburg and Loudoun county.
Stayed 2 nights in Oct 2025

About the host

Hosted by Owner/Property Manager

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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