11+ Vacation Rentals Near Trump Winery |
  1. USA
  2. Virginia
  3. Charlottesville
  4. Trump Winery

Montgomery Cottages - Vacation Rentals in Trump Winery

Loveshack, a charming tiny house on a 5 acre farm From US $232
         

9.4 (10 Reviews)
Cottage
Loveshack, a charming tiny house on a 5 acre farm
  • Air Conditioner
  • Parking
  • TV

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Charming Retreat in Charlottesville w/Deck! From US $448
         

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New
Cottage
Charming Retreat in Charlottesville w/Deck!
  • Air Conditioner
  • Parking
  • Security/Safety

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Fairwood Cottages- Both Cottages, Getaway Close to Town
New
From US $468
         

New
Cottage
Fairwood Cottages- Both Cottages, Getaway Close to Town
  • Air Conditioner
  • Parking
  • TV

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Azalea Cottage - adorable cottage within one mile of the University of Virginia From US $276
         

10.0 (138 Reviews)
Cottage
Azalea Cottage - adorable cottage within one mile of the University of Virginia
  • Air Conditioner
  • Parking
  • TV

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Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries From US $198
         

10.0 (30 Reviews)
Cottage
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
  • Air Conditioner
  • Parking
  • TV

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Clear Sky Cottage - A Spacious 1 BR Cottage Close to Charlottesville & Wineries. From US $175
         

10.0 (5 Reviews)
Cottage
Clear Sky Cottage - A Spacious 1 BR Cottage Close to Charlottesville & Wineries.
  • Air Conditioner
  • Parking
  • TV

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Cozy cottage-15min walk to historic downtown mall!n From US $344
         

9.0 (2 Reviews)
Cottage
Cozy cottage-15min walk to historic downtown mall!n
  • Air Conditioner
  • Parking
  • TV

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Cozy Stonehenge Cottage- Fenced yard, Close to Hospital, Walk to Downtown From US $298
         

New
Cottage
Cozy Stonehenge Cottage- Fenced yard, Close to Hospital, Walk to Downtown

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Eclectic Esmont Cottage: Pets Welcome! From US $167
         

5.0 (1 Review)
Cottage
Eclectic Esmont Cottage: Pets Welcome!
  • Pet Friendly
  • Bedding/Linens
  • Child Friendly

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Pet-Friendly Esmont Cabin on Historic Farm From US $260
         

New
Cottage
Pet-Friendly Esmont Cabin on Historic Farm
  • Air Conditioner
  • Pet Friendly
  • TV

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Blackberry Cottage: Cozy Perfection Close to Everything- Pet Friendly From US $165
         

New
Cottage
Blackberry Cottage: Cozy Perfection Close to Everything- Pet Friendly
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens

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★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Trump Winery.

Weather in Trump Winery

View the weather forecast for Trump Winery before booking your Trump Winery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Trump Winery, VA

Montgomerycottages offers a large selection of top attractions around Trump Winery. Research things to do on your vacation before you visit Trump Winery.


University of Virginia Monticello Downtown Mall John Paul Jones Arena University of Virginia Hospital The Jefferson Theater Paramount Theater Charlottesville Pavilion Pippin Hill Farm & Vineyards Scott Stadium Michie Tavern Fashion Square Mall University Hall at University of Virginia Jefferson Vineyards Arcady Vineyard Layz S Ranch Corner district Barracks Road Shopping Center Carter Mountain Orchard Rivanna Trails