Cottage in Shenandoah Valley, VA
2 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Well priced for this locationPriced under area average
About this cottage rental
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.
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.
Amenities at Charming Writer's Cottage in the Heart of Middleburg
Non-smoking
Pets allowed
Map of Shenandoah Valley, VA
Ratings and reviews
Summary of reviewsThe property received glowing reviews for its convenient location, charming and comfortable cottage, responsive and accommodating host, historical charm, and well-equipped amenities.
10 / 10Outstanding·Jun 2026
Charming and conveniently located.
10 / 10Outstanding·May 2026
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.
10 / 10Outstanding·May 2026
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!
6 / 10Average·Mar 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.
$$$$
Top rated by guests
9.7Outstanding
(170 Ratings)
The property received glowing reviews for its convenient location, charming and comfortable cottage, responsive and accommodating host, historical charm, and well-equipped amenities.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
