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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076

The Outpost Cottage In Upperville/Middleburg

Bedrooms 1
Property type cottage
Minimum Stay 2 nights


About the property

1 Bedroom, 1 Bathroom, Sleeps 2

Our idyllic cottage is nestled in the foothills of the Blue Ridge mountains, in the quaint and historical village of Upperville, Virginia-only 10 minutes away from Middleburg. Newly renovated with an open floor plan, queen-sized bed, a full kitchen with vintage marble countertops and a brand new bath. We have furnished The Cottage with antiques from around the globe sourced from our destination shops The Outpost in Middleburg and The Keep in Upperville. Perfect for weekend retreats and fully equipped for extended stays. Adjacent to our antiques and interiors shop The Keep, within walking distance of Hunter's Head Pub and The Local Taste Wine Bar. Full of style, light and airy and supremely comfortable, you'll never want to leave.


Upperville Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM / Check-out: 10:00 AM
  • Max. occupancy: 2
  • Minimum Age Limit for Renters ...
  • not suitable for children
  • pets not allowed
  • non smoking only
Location Type:
  • Village
  • Away From It All
  • Romantic
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 2 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • 1 Bedroom, Sleeps 2
  • Books
  • DVD Player
  • Satellite / Cable
  • Television
  • Video Library
  • Lawn / Garden
  • wheelchair inaccessible
  • arboretum
  • churches
  • winery tours
Leisure Activities:
  • antiquing
  • scenic drives
  • sight seeing


Wonderful! 4.9/5 -
(16 traveler reviews)

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The Outpost Cottage In Upperville/Middleburg
average rating of 4.9375 based on 16 reviews

Perfect getaway

  • 5 of 5

This is the perfect spot to get away from it all and enjoy the Middleburg area and local wineries ... or simply cocoon. The kitchen is beautifully equipped, the bed super comfy, the HVAC is quiet & works well, and the location is fabulous. There's a library of books, magazines and DVDs. Food at the Hunters Head is sourced locally and good quality if you like to 'eat clean' ingredients. I highly recommend this place and will be booking again!

  • Submitted: Mar 16, 2017
  • Stayed: March 2017
  • Source: HomeAway
Owner's Response: Thank you so much for your kind words. I'm happy that you enjoyed your stay and that it was a restful one for you! We hope you'll be able to return to The Cottage soon.
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Fantastic cottage in Upperville!

  • 5 of 5

Loved our long weekend in Upperville! Fantastic cottage with convenient access to Middleburg (10 minute drive). Will definitely come back.

  • Submitted: Dec 18, 2017
  • Stayed: December 2017
  • Source: HomeAway
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  • 5 of 5

The cottage is lovely!

  • Submitted: Dec 6, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Atlanta, Ga

Amazing value!!

  • 5 of 5

The Cottage was even more charming than the photos and descriptions! Clean, comfortable, quiet, and perfectly situated to enjoy the many things to do in and around town! The hosts were communicative and accommodating!

  • Submitted: Nov 5, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Picture perfect location for a stay in northern VA!

  • 5 of 5

The property was impeccably decorated with lots of attention paid to detail. Very clean, comfortable and with all the amenities. Picturesque views of both the town in the front and the rolling hills in the rear. Perfect place for a romantic weekend getaway. Easy access to hiking trails, Shopping in Middleburg and plenty of wineries and breweries. The only thing I would add is a fire pit in the back. Highly recommend The Cottage!

  • Submitted: Oct 29, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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United States, PA, Lancaster

Beautiful place in a beautiful location!

  • 5 of 5

My wife and I spent several days at The Cottage and it was a wonderful experience. The accommodations were outstanding, very clean and very tastefully decorated, it really feels like your home! The view from the rear of the property was beautiful. Upperville and The Cottage are an outstanding location to enjoy the beauty of the region, hiking, cycling and wine tasting all at your fingertips. Loved our stay and look forward to many return visits.

  • Submitted: Oct 9, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Pam Foster
Member since: 2016
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
February 23, 2018


Car: necessary

The Cottage is just a short drive from many great wineries, including Boxwood, Greenhill, Cana, RdV and Delaplane Cellars. Some of our favorite nearby restaurants include Hunter's Head Tavern, The Goodstone Inn, The Ashby Inn, The Red Fox and Girasole. There are wonderful hikes and walks at Sky Meadow State Park and the Virginia State Arboretum, both of which are a ten-minute drive.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $50
Damage Deposit $250

Owner's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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