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Charming Writer's Cottage in the Heart of Middleburg

Cottage in Middleburg with kitchen and patio

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

Tavern Office 1
Tavern - Office 2
Tavern - Office 3
1820 Historic Home - Dormitory for the first Middleburg Academy
Living room

Reviews

9.8 out of 10
Exceptional
1 bedroom1+ bathroomSleeps 2

Popular amenities

  • Dryer
  • Washer
  • Kitchen

Explore the area

View map
Middleburg, VA
  • Place, Middleburg Historic District
    ‪6 min walk‬
  • Place, Red Fox Fine Art
    ‪6 min walk‬
  • Place, Middleburg Community Center
    ‪9 min walk‬
  • Airport, Washington, DC (IAD-Washington Dulles Intl.)
    ‪31 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.
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 $172+ 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 $245.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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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

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.
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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
  • 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

  • ‪The Goodstone Inn & Estate - ‬9 min drive
  • ‪Red Horse Tavern - ‬9 min walk
  • ‪King Street Oyster Bar - ‬6 min walk
  • ‪Lost Barrel Brewing - ‬4 min drive
  • ‪Gold Cup Wine Bar - ‬17 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 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 136 out of 152 reviews
Rating 8 - Good. 12 out of 152 reviews
Rating 6 - Okay. 4 out of 152 reviews
Rating 4 - Poor. 0 out of 152 reviews
Rating 2 - Terrible. 0 out of 152 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

Sandy S.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Maxwell D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Oct 2025

10/10 Excellent

Christopher B.

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

10/10 Excellent

Chuck E.

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

10/10 Excellent

Amanda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Oct 2025

8/10 Good

Carolyn F.

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

10/10 Excellent

David S.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Robert S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025

10/10 Excellent

Kate P.

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

Great weekend getaway

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.
Stayed 2 nights in Aug 2025

10/10 Excellent

Jim S.

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

Small town charm

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.
Stayed 2 nights in Jul 2025

10/10 Excellent

Michele S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Sep 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jun 2025

10/10 Excellent

Lisa W.

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

QUAINT & CONVENIENT

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.
Stayed 4 nights in Jul 2025

10/10 Excellent

Jackie B.

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

Home y

Amazing hosts, cozy and well equipt home - close walk to town. We couldn't have had better place our 2 fur baby!
Stayed 2 nights in May 2025

10/10 Excellent

David W.

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

10/10 Excellent

Cameron F.

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

Convenient and as Expected

Title says it all
Stayed 7 nights in Jun 2025

8/10 Good

Jacklyn C.

Liked: Check-in, communication, location, listing accuracy

Good location

Easy to walk to nearby shops and restaurants. Home is dated and ceilings are low (6’5” husband had to duck on first floor). There was mold in the shower and AC unit, and cobwebs throughout.
Stayed 3 nights in May 2025

10/10 Excellent

Kathleen T., Bel Air, MD 21014, USA

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

10/10 Excellent

Susan H.

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

Historic gem

Comfortable and decorated beautifully . Very Middleburg!
Stayed 2 nights in Dec 2024

10/10 Excellent

Lisa A.

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

Right in downtown Middleburg

This is my 2nd stay at this sweet cottage, & I highly recommend. It's walkable to restaurants & shopping. The host, Michael is knowledgeable & quick to communicate.
Stayed 8 nights in Jan 2025

10/10 Excellent

Carol W.

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

Great location

This very sweet home is located a short walk to and through the town. The house is well-equipped and spacious for its size. Michael was easy to communicate with and was very gracious about extending my check-out time. HIghly recommended.
Stayed 2 nights in Apr 2025

10/10 Excellent

Christine M.

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

Adorable cottage

Charming cottage in the heart of Middleburg. Easy walk to shops and restaurants. Owner very responsive to all requests!
Stayed 3 nights in Oct 2024

10/10 Excellent

Alana G.

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

Great cottage for a quiet weekend!

This was a lovely place to stay for a weekend in Middleburg. Excellent location, walking distance to the restaurants and shops. Michael is a great host.
Stayed 3 nights in Dec 2023

About the host

Hosted by Owner/Property Manager

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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