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Vacation rentals in The Plains

Vacation rentals in The Plains

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in The Plains

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • The Whistle Stop
    SUPERHOSTEntire apartment · 6 guests · 5 beds · 1 bath
    The Whistle Stop

    Historic, renovated, train station in the heart of Virginia hunt and wine country. This private oasis sits on the second floor above three gorgeous art studios belonging to local artists. Enroll in an art workshop, enjoy twilight polo and horse races at Great Meadows, or find yourself having a romantic dinner in our little village of The Plains.

    What guests are saying:

    “Caro's place is the epitome of an authentic experience. The apartment is lovely, comfortable, and historic. Nice touches, too -- coffee, muffins, Perriers! It's an old train station that stopped being used in the 1940s, but the train still runs by. It's quirky and fun IMHO. Beautiful art studios below. Stairs to the apartment are steep-ish, so if you over imbibe, be careful! Cute restaurants and shops within walking distance and close to Middleburg and Marshall. Toot!”

  • The Cottage on Main-Virginia Wine & Horse Country
    Entire cottage · 4 guests · 2 beds · 1 bath
    The Cottage on Main-Virginia Wine & Horse Country

    The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!

    What guests are saying:

    “A beautiful, fresh and inviting space with high end and thoughtful touches throughout. David and Karen were easy to communicate with and accommodated our early check in. We loved walking through their beautiful garden and my 3 year old daughter was beyond jazzed to take home one of the gorgeous freshly cut pink flowers they left for us.”

  • "When Pigs Fly"  Wine Country!  Ale Trail!
    SUPERHOSTEntire loft · 2 guests · 1 bed · 1 bath
    "When Pigs Fly" Wine Country! Ale Trail!

    Located between Middleburg, VA and Purcellville, VA, our space is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. We offer an efficiency loft with views from every window. Although compact, we have provided all of the amenities you will need for a pleasant stay. We love our dogs and know you love yours too! We welcome your dogs while you visit. The only thing we ask is that you crate them if they are left alone.

    What guests are saying:

    “I stayed for 6 weeks at “When Pigs Fly” and loved it! Theresa and Rob were excellent hosts and went above and beyond to make sure I had everything I needed for my stay. The loft was clean, beautifully decorated, and included all the amenities needed for a long stay. I brought my dog with me, and she had plenty of space to walk around outside and around the loft. The location was beautiful, and the perfect place for a long stay or a quick trip.”

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for The Plains vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in The Plains

Comfort Private Room (V3)
Private room
Comfort Private Room (V3)
Price:$33 / night
Rose End
Entire apartment
Rose End
Price:$75 / night
Fox Cross Cottage in Virginia Horse & Wine Country
SUPERHOSTEntire house
Fox Cross Cottage in Virginia Horse & Wine Country
Price:$189 / night
Lodge on the Lake
Entire cabin
Lodge on the Lake
Price:$225 / night
Haymarket home with view
SUPERHOSTPrivate room
Haymarket home with view
Price:$48 / night
Great Views
SUPERHOSTPrivate room
Great Views
Price:$34 / night
Noctiluca Farm & Wine Trail Getaway
SUPERHOSTEntire apartment
Noctiluca Farm & Wine Trail Getaway
Price:$89 / night
Charming bed/bath w/views & space to telecommute
SUPERHOSTPrivate room
Charming bed/bath w/views & space to telecommute
Price:$42 / night
Farm Retreat in the Heart of Loudoun Wine Country!
SUPERHOSTFarm stay
Farm Retreat in the Heart of Loudoun Wine Country!
Price:$123 / night
Horse farm near Manassas Battlefield.
SUPERHOSTEntire guest suite
Horse farm near Manassas Battlefield.
Price:$60 / night
Cottage in Prime Wine and Horse Country Location
SUPERHOSTEntire house
Cottage in Prime Wine and Horse Country Location
Price:$300 / night
Hunt Box  on 1700's Horse Farm/Wedding Venue
SUPERHOSTFarm stay
Hunt Box on 1700's Horse Farm/Wedding Venue
Price:$125 / night
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