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.
Our prices include all fees. No hidden fees.
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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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
About the area
Middleburg
Middleburg is home to this cottage. Tudor Day Spa and The Boxwood Winery 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.
Middleburg Historic District - 6 min walk - 0.6 km
Red Fox Fine Art - 6 min walk - 0.6 km
Tudor Day Spa - 8 min walk - 0.7 km
National Sporting Library & Museum - 9 min walk - 0.8 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 Goodstone Inn & Estate - 9 min drive
Lost Barrel Brewing - 4 min drive
Gold Cup Wine Bar - 17 min walk
King Street Oyster Bar - 6 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 26 Mar 2026, prices found for a 1-night stay for 2 adults at Charming Writer's Cottage in the Heart of Middleburg on 8 Jun 2026 start from £155, 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 Tudor Day Spa 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.
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!
Absolutely charming cottage with so many thoughtful details. I just loved it. Great location -in walking distance to town. And the owners were responsive.
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.
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!
Everything was excellent. The host is wonderful and very polite and communicative. The writer theme and all the small touches were adorable. Would definitely go back :-) !
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.
The host is exceptionally responsive and as accommodating as can be expected from anyone renting a property in a prime area. The cottage is walking distance to everything in town and a very short drive to numerous wineries and other attractions. The cottage is quaint for sure, but a couple would certainly enjoy their stay for a weekend getaway.
The cottage was very quaint and so close to all the Middleburg fun! The Owner went above and beyond to provide information and respond to questions. We had a terrific experience!
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.
We enjoyed our stay in this charming, historic home. The space was spacious and well laid out, with a large bedroom and bathroom, small kitchen, and plenty of living and dining space. The house had a lot of character, and we appreciated the ample parking.
Great location for staying in Middleburg! Well maintained property with good space and in the perfect location for walking the main street area with plenty of shops & restaurants. Would definitely rent again in the Fall for the foliage and the close proximity to wineries.
Fantastic place and great location among Middlesburg with everything within walking distance! Host communicated and even left a gift for our anniversary. Would highly recommend.
Cozy, clean cottage. All the comforts of home. Our host was quick to respond with any questions we had. Great location as it was easy to walk to restaurants and stores. An easy drive to numerous wineries and breweries as well. We definitely would stay here again.
Great location! Walkable to dining and shopping. Nicely appointed home-clean,good quality FLUFFY towels. Great mattress! Host EXTREMELY responsive and helpful. You will definitely know you are in “horse country” from the decor! Giddy Up! Loved it!
VRBO stay in Middleberg for Mountville folk festival
My husband and I found the perfect place to stay in Middleberg for the Mountville music festival! The best part is that we were able to bring our sweet kitty cat! We loved the cat friendly decor in the house including a Hemingway photo with a kitty. Highly recommend!
I can't enough great things about this sweet little spot! Its decor is so charming and the location couldn't be more convenient to see the town or stroll through the neighborhood. Plenty of yard space in the rear of the home to enjoy - has a big shady tree over the deck to enjoy the afternoon or for morning coffee. Michael is an outstanding host who truly wants you to have a magical stay.
Lisa W.
Stayed 4 nights in Jul 2025
About the host
Hosted by Owner/Property Manager
Languages:
English
Premier Host
They consistently provide great experiences for their guests