Charming Writer's Cottage in the Heart of Middleburg

Middleburg, Virginia
$240 avg/night
Minimum Stay 2 Nights
Bed 1

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 2

Max Sleeps

Night 2 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 50 Lbs Per Pet) Pet Friendly Service Animals Exempt From Fees Welcoming Cats And Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided
  • GENERAL

    Property Does Not Allow Children
  • KITCHEN

    Coffee/tea Maker Electric Kettle Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Garden Outdoor Furniture Patio
  • BATHROOMS

    1.5 Bathrooms Hair Dryer Shower Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Horse Riding Nearby
  • ENTERTAINMENT

    Books Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Availability

Review Review

  • Linda K.

    Submitted Apr 9, 2026

    Stayed Apr 7, 2026

    Great location, host, and house!

  • Ryan C.

    Submitted Mar 22, 2026

    Stayed Mar 20, 2026

    Great place to stay. Cozy and convenient to everything Middleburg had to offer. Host was very friendly and responsive.

  • Nancy T.

    Submitted Mar 1, 2026

    Stayed Feb 27, 2026

    Absolutely charming cottage with so many thoughtful details. I just loved it. Great location -in walking distance to town. And the owners were responsive.

  • Nancy R.

    Submitted Feb 15, 2026

    Stayed Feb 13, 2026

    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!

  • Cindy B.

    Submitted Jan 4, 2026

    Stayed Dec 12, 2025

    Unfortunately I was not told that there wasn’t heat on the second floor (bedroom & bath). It was a very cold weekend and when I asked about the heat, I got blasted by the owner in 3 text messages which I saved. He did refund my money but telling me on Saturday morning to pack up and get out was very shocking and just overall unprofessional. It ruined my weekend with my granddaughters that we were so looking forward to but instead ended up traveling home on Saturday So very disappointing

  • Kathleen S.

    Submitted Dec 7, 2025

    Stayed Dec 5, 2025

    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.

  • Kasha T.

    Submitted Nov 18, 2025

    Stayed Nov 7, 2025

    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 :-) !

  • Devin B.

    Submitted Nov 16, 2025

    Stayed Nov 14, 2025

    Clean, cozy, lovely cottage. Friendly and accommodating host. Great location.

  • Sandy S.

    Submitted Nov 10, 2025

    Stayed Nov 3, 2025

    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!

  • Maxwell D.

    Submitted Nov 3, 2025

    Stayed Oct 31, 2025

    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.

  • Amanda B.

    Submitted Oct 26, 2025

    Stayed Oct 24, 2025

    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!

  • Chuck E.

    Submitted Oct 25, 2025

    Stayed Oct 22, 2025

    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.

  • David S.

    Submitted Oct 19, 2025

    Stayed Oct 16, 2025

    Michael is great and very responsive. The location is wonderful for activities in and around Middleburg.

  • Carolyn F.

    Submitted Oct 11, 2025

    Stayed Oct 5, 2025

    Kitchen was well stocked

  • Michele S.

    Submitted Sep 28, 2025

    Stayed Sep 26, 2025

    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!

  • Submitted Sep 22, 2025

    Stayed Sep 19, 2025

    Wonderful location, very cute cottage

  • Submitted Sep 1, 2025

    Stayed Aug 29, 2025

    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.

  • Christopher B.

    Submitted Aug 21, 2025

    Stayed Aug 15, 2025

    Nice little cottage walking distance from everything in Middleburg. Would definitely stay again!

  • Robert S.

    Submitted Aug 12, 2025

    Stayed Aug 8, 2025

    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.

  • Kate P.

    Submitted Aug 4, 2025

    Stayed Aug 1, 2025

    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.

  • Jim S.

    Submitted Jul 27, 2025

    Stayed Jul 25, 2025

    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.

  • Lisa W.

    Submitted Jul 8, 2025

    Stayed Jul 3, 2025

    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.

  • Elizabeth K.

    Submitted Jul 7, 2025

    Stayed Jun 19, 2025

    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!

  • Submitted Jun 17, 2025

    Stayed Jun 12, 2025

    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.

  • Cameron F.

    Submitted Jun 10, 2025

    Stayed Jun 1, 2025

    Title says it all

  • Jacklyn C.

    Submitted Jun 1, 2025

    Stayed May 29, 2025

    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.

  • Jackie B.

    Submitted May 17, 2025

    Stayed May 15, 2025

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

  • Carol W.

    Submitted Apr 6, 2025

    Stayed Apr 3, 2025

    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.

  • Janet R.

    Submitted Mar 30, 2025

    Stayed Mar 2, 2025

    The location of this very small cottage is terrific for walking right into town. The host is very friendly and accommodating. That said, the cottage needs a thorough cleaning inside and out. There is mold in the shower, a collection of used soap bars and other detritus in the closet and significant rot on the exterior. Needs to be cleaned out and. Leaned up.

  • Alan M.

    Submitted Feb 2, 2025

    Stayed Feb 1, 2025

    Michael was wonderful in accommodating my wife and I for a one-night stay, all we could squeeze in, to celebrate her birthday in the town we love to visit. We’ve been to Middleburg many times over the years and are all too familiar with how difficult combining convenience of location (ie town walkable) and budget be- this accomodation ticked both boxes!!

  • Lisa A.

    Submitted Jan 27, 2025

    Stayed Jan 12, 2025

    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.

  • Ashley B.

    Submitted Jan 22, 2025

    Stayed Jan 10, 2025

    What’s not to love? It was so cute, exactly/even better than the pictures and the decoration completely captured the Virginia horse country ambience. It was literally walkable to everywhere. You would wanna go in Middleburg and only five minutes away from salmon resort and the good Stone Inn. Parking was super easy and it made exploring Middleburg easier because we did not have to worry about parking in the downtown area. The hustles also fantastic and really communicative and made sure everything was taken for your night. I was there to celebrate an engagement and he went above and beyond to make a special weekend for us. Thank you so much to the house for a great weekend and I would absolutely recommend anyone looking to stay in Molberg to book here before it’s booked up by someone else. You absolutely won’t regret it.

  • Susan H.

    Submitted Dec 8, 2024

    Stayed Dec 6, 2024

    Comfortable and decorated beautifully . Very Middleburg!

  • Jim G.

    Submitted Nov 4, 2024

    Stayed Nov 1, 2024

    The cottage was cute and location was just what we wanted. You can walk to any where in Middleberg. It was lovely weekend to visit.

  • David S.

    Submitted Oct 21, 2024

    Stayed Oct 17, 2024

    Lovely place on edge of town. Easy walking to Everything.

  • Christine M.

    Submitted Oct 6, 2024

    Stayed Oct 3, 2024

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

  • Margaret F.

    Submitted Oct 5, 2024

    Stayed Sep 26, 2024

    We enjoyed staying here with our dog. Everything was very clean and bright! clean,

  • Angela W.

    Submitted Sep 16, 2024

    Stayed Sep 10, 2024

    This home is precious, comfortable and walkable to many shops, restaurants and the Salamander Resort. The host was extremely responsive and helpful with dinner suggestions. 5 stars!

  • Lisa A.

    Submitted Sep 13, 2024

    Stayed Aug 24, 2024

    I stayed here during part of a heatwave (94*) and the house stayed cool, including the upstairs. Bed is soft, comfy, but linens could use an update. The stairs to the second floor look like they could be difficult, but are so easy (barefooted :) to use. The kitchen accommodates a simple meal. And, the backyard deck is a most delightful hang out, for a meal or watching the small wildlife. Eating out at fabulous restaurants or shopping is just a minute walk away. 40 minutes to the north entrance of Shenandoah Nation park

  • Joy B.

    Submitted Aug 4, 2024

    Stayed Aug 2, 2024

    We had a wonderful stay at the cottage. Perfect for a couple’s getaway. Beautiful town with loads of shopping and cafes. Thank you, Michael!

Your dates are Available!

Total

Includes taxes and fees
$347+
View details