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

Aston Waikoloa Colony Villas - Vacation Rentals in Trump Winery

Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive From US $288
         

9.8 (171 Reviews)
House
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive
  • Air Conditioner
  • Parking
  • Pet Friendly

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Charming Retreat in Charlottesville with Deck! From US $432
         

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10.0 (3 Reviews)
House
Charming Retreat in Charlottesville with Deck!
  • Parking
  • Accessibility
  • Security/Safety

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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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Downtown Carriage House | 1 BR Loft close to the historic downtown mall From US $190
         

9.4 (87 Reviews)
Apartment
Downtown Carriage House | 1 BR Loft close to the historic downtown mall
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Navel Nalle - Downtown Bungalow, Patio, Parking From US $1,016
         

10.0 (1 Review)
House
The Navel Nalle - Downtown Bungalow, Patio, Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fairfield Inn & Suites by Marriott Charlottesville Downtown/University Area From US $126
         

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9.0 (948 Reviews)
Hotel
Fairfield Inn & Suites by Marriott Charlottesville Downtown/University Area
  • Air Conditioner
  • Parking
  • Pool

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Historic Beauty and Walkable to Everywhere From US $318
         

10.0 (61 Reviews)
House
Historic Beauty and Walkable to Everywhere
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sonsak - Unit 4 From US $188
         

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9.9 (31 Reviews)
Apartment
Sonsak - Unit 4
  • Air Conditioner
  • Parking
  • View

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Home2 Suites by Hilton Charlottesville Downtown From US $135
         

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8.8 (760 Reviews)
Hotel
Home2 Suites by Hilton Charlottesville Downtown
  • Air Conditioner
  • Parking
  • Pool

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Honey B—Honey House 2. Beautiful vacation home near UVA, Monticello and downtown From US $242
         

10.0 (55 Reviews)
House
Honey B—Honey House 2. Beautiful vacation home near UVA, Monticello and downtown
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Honey House—beautiful modern loft near with UVA, Monticello and downtown From US $319
         

10.0 (52 Reviews)
House
Honey House—beautiful modern loft near with UVA, Monticello and downtown
  • Air Conditioner
  • Parking
  • TV

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Warner House | Charming Home in Belmont- walk Downtown From US $1,242
         

10.0 (42 Reviews)
House
Warner House | Charming Home in Belmont- walk Downtown
  • Air Conditioner
  • Parking
  • TV

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Fairytale Loft Suite | 1 bed, 1 bath Luxury Apartment in Downtown Belmont From US $225
         

10.0 (40 Reviews)
Apartment
Fairytale Loft Suite | 1 bed, 1 bath Luxury Apartment in Downtown Belmont
  • Air Conditioner
  • Parking
  • TV

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Hill Street House walk to UVA Stadium/Fry's Spring From US $402
         

10.0 (36 Reviews)
House
Hill Street House walk to UVA Stadium/Fry's Spring
  • Air Conditioner
  • Parking
  • TV

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Belmont Oasis I Downtown Cville | 3 bed, 2.5 bath | Sleeps 6 A, 2 C From US $523
         

10.0 (35 Reviews)
House
Belmont Oasis I Downtown Cville | 3 bed, 2.5 bath | Sleeps 6 A, 2 C
  • Air Conditioner
  • Parking
  • TV

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New Luxury Modern Farmhouse, Downtown C'Ville From US $996
         

10.0 (29 Reviews)
House
New Luxury Modern Farmhouse, Downtown C'Ville
  • Air Conditioner
  • Parking
  • TV

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Unit 5 - Cozy Lower Level Studio Suite From US $127
         

10.0 (28 Reviews)
Condo
Unit 5 - Cozy Lower Level Studio Suite
  • Air Conditioner
  • Parking
  • TV

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Mont G | 30 + Day Rental | Walk Downtown From US $332
         

10.0 (24 Reviews)
House
Mont G | 30 + Day Rental | Walk Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautifully Rustic Cabin just 10 minutes from UVA, with pool! From US $687
         

10.0 (22 Reviews)
Cabin
Beautifully Rustic Cabin just 10 minutes from UVA, with pool!
  • Air Conditioner
  • Parking
  • Pool

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Unit 3 - Luxury King Suite with Private Balcony From US $187
         

10.0 (21 Reviews)
Condo
Unit 3 - Luxury King Suite with Private Balcony
  • Air Conditioner
  • Parking
  • TV

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Unit 1 Expansive Luxury Suite for up to 4 Persons From US $224
         

10.0 (18 Reviews)
Condo
Unit 1 Expansive Luxury Suite for up to 4 Persons
  • Air Conditioner
  • Parking
  • TV

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Keelona Cottage 2 BR 2 BA near vineyards From US $424
         

10.0 (16 Reviews)
House
Keelona Cottage 2 BR 2 BA near vineyards
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Charming Retreat in Charlottesville w/Deck! From US $387
         

10.0 (15 Reviews)
House
Charming Retreat in Charlottesville w/Deck!
  • Air Conditioner
  • Parking
  • TV

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Unit 4 - Luxury King Suite with Private Balcony From US $186
         

10.0 (14 Reviews)
Condo
Unit 4 - Luxury King Suite with Private Balcony
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Astonwaikoloacolonyvillas makes it easy to compare the best listings on Astonwaikoloacolonyvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Astonwaikoloacolonyvillas 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

Astonwaikoloacolonyvillas 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

Trump Winery Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Trump Winery?

There are a lot of options in Trump Winery. If you plan on staying in the Trump Winery area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Trump Winery:

How many vacation rentals are available in Trump Winery?

Currently, the total number of properties listed in 2026 is over 245 in the Trump Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Trump Winery.