1664 Bailey's Retreat Rd, Charlottesville, 22901, United States
  based on 12 reviews
  •   8
  •   3
  •   1
  • SQF 2,200
  •  wifi
  •  A/C
  •  Parking


The Space 

This 3 bedroom 2 story house  is a perfect place for gathering with friends and family.  The living room is super accommodating with wide screen TV and comfy furniture.  With this open concept living space, you're always part of the festivities. Upstairs there is a seating area with a wet bar that leads to a deck with views of the mountains. Perfect for sunset watching. There are 3 bedrooms and 1.5 bathrooms. Bedroom configuration: Master bedroom has 1 queen bed, Second bedroom has 2 queen beds and 3rd bedroom has  2 twins. The all  have designer linens and new bedding. 

Guest Access: 

We are happy to share much of our retreat with guests.  Bring a picnic or a bottle of wine the Adirondack chairs on our lawn terrace and marvel at one of our stunning sunsets or starry nights.  Grab guitars or simply gather with family and friends for a fireside chat at out outdoor pavilion.   Situated on a country lane off of a country road, you are welcome to stretch your legs on a six mile walk.  Bailey’s Retreat offers plenty to do and plenty of places to do nothing.  We hope you enjoy our family’s homestead as much as we do. 

House Manual and Policies


1 Bathroom, 3 Bedroom, 1 Dining-Room, 1 Kitchen, 1 Living room, 1 Toilet

  • Sleeping
    2 Queen bed, 2 Single bed
  • Cooking
    Coffee machine, Cooking utensils, Dishwasher, Kitchen stove, Microwave, Oven, Refrigerator
  • Heating/Cooling
    Air conditioning, Ceiling fans, Central heating
  • Outside
    Private Balcony, Private Terrace
  • Entertainment
    Wireless Broadband Internet, TV (Cable)
  • Sanitary
    Hair dryer, Shower
  • Laundry
    Iron & Board
  • 1 Bathroom, 3 Bedroom, 1 Dining-Room, 1 Kitchen, 1 Living room, 1 Toilet
  • Parking
    Parking Included
Pets not allowed, Smoking not allowed,Credit cards accepted, Accessible 24/7, Laundry service Included
Check in:
4:00 PM
Check out:
10:00 AM

1664 Bailey's Retreat Rd , Charlottesville, 22901, United States

based on 12 reviews
Kay (Richmond)

Incredible!! We had an absolutely wonderful stay. The accommodations were clean, comfortable, private and quiet. Take the private wine tour and be sure to ask for Jimmy! Duners restaurant and Hazy Days vineyard are a must!

Mature couple  |  stayed in 11/2021

Natali Rhines (Raleigh, NC)
Beautiful location!

Me, my husband and 2 friends were motorcycling in the area and found Bailey’s Retreat online. We booked the farmhouse and it was plenty big and homey. Spacious downstairs and nice deck upstairs with a great view. I loved the fire pit area on the property but sadly we weren’t there long enough to enjoy it. The ride to the property is really nice! The entire property is very well maintained, peaceful and quiet. I recommend this place to anyone in the area!

Group  |  stayed in 10/2020

Annette (Newcomb)
Beautiful setting

Bailey’s Farmhouse was perfect. Clean, comfortable, spacious. The beds were very comfortable, the shower modern, plenty of towels for all of us! Woke up and had coffee on the patio to the sounds of birdsong. Lovely views, privacy - it’s all here in one nice package! We will definitely come back!

Group  |  stayed in 7/2020


We stayed at the Farmhouse for my sister's Bachelorette weekend. The house very comfortably slept 7 of us and had tons of room for games and lounging. This location is beautiful! So convenient to several wineries and breweries and many places to hike. Highly recommend the bailey's retreat wine tour during your stay! Roseanne was wonderful to communicate with every step of the way. Highly recommend! Would definitely stay here again.

Group  |  stayed in 3/2020

Kaitlyn (Farmhouse )
Girls Trip

We spent a weekend at Baileys Retreat in the Farmhouse. Absolutely stunning views, amazing wineries and beautiful area. This stay was everything as advertised plus some! I would highly recommend Baileys Retreat to anyone that loves the outdoors or just looking for a peaceful getaway.

Group  |  stayed in 2/2020

Vb (Ky)

We've just returned from the most wonderful “Girl trip” stay in the farmhouse at Bailey’s Retreat. There are so many reasons to love this place... morning coffee on the back deck while watching deer run across the fields. The upstairs of the house has a cute and cozy setting area that we loved. Sunset viewing from the hilltop was amazing. Roseann and Bill are gracious hosts who are readily available if needed. We appreciate that they provided us with a nice supply of bottled water... much appreciated since the temps were crazy hot during our stay. Honestly... we hated to leave. We really really do hope to return.

Not specified  |  stayed in 10/2019

Mary (Hampton Roads)
40th Birthday Getaway

We came as a group of 5 longtime friends for my 40th birthday. The house was perfect for this type of getaway. The views are amazing and the winery tour was so much fun! I would definitely recommend Bailey's Retreat to anyone simply looking for an amazing time!

Group  |  stayed in 10/2019

Amanda (Farmhouse)
Beautifully Perfect

My best friend and I got away for the weekend for a little momcation. The farmhouse was comfortable and clean and had everything we needed. The view from the top of the hill was beautiful. The wine tour was excellent. Bill was our tour guide and he picked some excellent wineries to take us to. We definitely recommend and will be coming again.

Group  |  stayed in 4/2019

Dan (Milwaukee, WI)

Everything was as advertised. We had a great stay. Highly recommended!

Group  |  stayed in 12/2018

allyson raphel (Kent Island Maryland)
Pre-50th birthday girls getaway weekend

Five Girlfriends and I came down for a long weekend ( Thursday to Monday ) to celebrate early 50th birthday. We all came from Annapolis, Eastern Shore/ Kent Island and North East Maryland. We had a wonderful time exploring around the towns- Crozet, Charlottesville, Monticello and of course Wine Tour. MUST MUST use their bus wine tour. Shannon, the driver was awesome. The house is spacious . The hostesses were gracious. Every mornings, we saw deer all around and it was beautiful, quiet and cozy. Thank you for everything!

Group  |  stayed in 11/2018

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Roseanne Bailey

super cool

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