Wineries with lodging on the Monticello Wine Trail

9 of the 44 wineries on the Monticello Wine Trail offer rooms or lodging on site.

Checked October 1, 2026 on each winery’s own website and the trail’s member listing.

• Veritas Vineyard & Winery

  Afton

  Family-owned winery for about 25 years; winemaker Emily Pelton makes sparkling, white and Bordeaux-style red wines.

  • food
  • lodging
  • dog-friendly
  • picnic
  • live music

• Barboursville Vineyards

  Barboursville

  Founded in 1976 by the Zonin wine family of Italy; known for its Octagon Bordeaux-style blend, Cabernet Franc and Nebbiolo, on an estate with ruins of a Jefferson-designed mansion.

  • $20 per person
  • food
  • lodging
  • dog-friendly
  • event venue

• Eastwood Farm & Winery

  Charlottesville

  Women-owned, multi-generational winery making wines, ciders and beers; a second tasting room, the Virginia Wine Collective, is at 1585 Avon Street Ext.

  • food
  • live music
  • lodging
  • dog-friendly
  • brewery/cidery

• Mount Ida Farm & Vineyard

  Charlottesville

  Tasting room and taphouse opened in 2018 at Mount Ida Reserve, with just over 20 acres of vines and farm-brewed beer.

  • food
  • brewery/cidery
  • lodging
  • dog-friendly
  • event venue

• Trump Winery

  Charlottesville

  Large estate with 227 acres of vines, known for traditional-method sparkling wines.

  • $25-$45 per self-guided flight
  • food
  • lodging
  • dog-friendly
  • event venue

• Mountain & Vine Vineyards and Winery

  Faber

  Terraced vineyard making French-inspired wines near Wintergreen.

  • lodging
  • dog-friendly
  • picnic
  • event venue

• Glass House Winery

  Free Union

  Winery with a tropical plant conservatory tasting room; also makes chocolates and beer.

  • lodging
  • dog-friendly
  • picnic
  • live music
  • brewery/cidery

• Lovingston Winery

  Lovingston

  100% estate-grown wines since 2003 from 11 acres and eight grape varieties, including Pinotage.

  • lodging
  • dog-friendly
  • picnic
  • food
  • event venue

• Pippin Hill Farm & Vineyards

  North Garden

  Vineyard with a farm-to-table kitchen and event venue on Bundoran Farm; wines made by Michael Shaps.

  • food
  • lodging
  • dog-friendly
  • event venue

More hotels near the trail Affiliate link.

More ways to plan the Monticello trail

• Dog-friendly wineries36 on this trail
• Wineries with food24 on this trail
• Wineries with live music17 on this trail
• Picnic-friendly wineries24 on this trail

Wineries with lodging on every trail we cover · All 44 wineries on the Monticello Wine Trail