A PLACE TO GET AWAY

Relax in Serenity

Perched on 50 rustic acres in Ivy,  Baileys Retreat is only moments to Charlottesville and offers cottages, cabins and homes with scenic serenity and stunning views. The Baileys started sharing their estate 15 years ago and have served thousands of guests and tenants from all over the world and are award-winning hostsThe rustic cabin is one of the most popular short-term rentals in Virginia and is an amazing property with historical significance. The cottages are available for mid-term and long-term rentals. They are wonderfully appointed and can be rented furnished or unfurnished, making them perfect for extended stays in the area. The retreat is moments to UVA, Monticello, the Shenandoah National Park and the central Virginia business and healthcare communities. So whether it’s a weekend stay, an employment project, temporary housing ormove to the country, Baileys Retreat serves your housing needs. 

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Wine Tours

Baileys Retreat Tour Company has been providing tours and transportation services to residents and visitors to the area since 2008. We will custom design a tour or outing for you and your group! We come to your location whether it be your home, office, Airbnb or hotel. Then we will return you safe and sound and happy! 

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Visit Charlottesville

Charlottesville, home to Thomas Jefferson’s Monticello and the University of Virginia, boasts a vibrant Downtown Mall, bountiful restaurants, and a wonderful place for a stroll. Visit Monticello, relax at wineries and breweries, or walk Downtown for boutique shops, gourmet food and cafes. For dining, drinks, and events, Charlottesville has to plenty to offer.

Hike the Blue Ridge

Explore the beauty of the Appalachian Mountains with hikes north and south on the Appalachian Trail, hikes to vistas, or longer strolls through mountains and streams. If you’re looking for beauty without the exercise, drive the Blue Ridge Parkway or Skyline Drive for an easy ride with endless overlooks.

Hikes Near Charlottesville

Cabins and Cottages

Baileys retreat offer a picturesque cabin for short getaway and 4 homey cottages for extended stays. The cabin was built originally in the 1800’s and is the original family homeplace, meticulously restored and renovated for contemporary needs . 

 The cottages are nestled  into the side of Bailey Mountain and are available  furnished or unfurnished,  with a cozy design  with access to viewing areas and an outdoor seating abound. For those seeking furnished housing the cottages are appointed  with incredible furnishings  for a relaxing  extended stay. All of the cottages are available with multiple pricing packages to suit all lease durations and furnishing preferences. 

Bailey's Retreat Cabin

Charlottesville, VA

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Baileys Retreat 3BR Home

Bailey's Retreat Farmhouse

Charlottesville, VA

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Cottage #1

Charlottesville, VA

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  • Our family enjoyed our stay at Bailey’s Retreat. The location was perfect for getting to all the activities we had planned in Charlottesville and had just the right about of space we needed for my husband and me and our two kids. It is such a peaceful setting!

    Jennifer

    Sep '2023

  • We absolutely loved our stay in this sweet, story book cabin! The views are stunning and it was so peaceful having our coffee on the porch in the mornings and enjoying a nice fire in the evenings. We also had the pleasure of meeting William, who was so warm and made us feel right at home. We will definitely be returning guests!

    Kathy

    Aug '2023

  • What a beautiful location! Awesome view of the mountains. Close enough to Charlottesville to enjoy the city, but far enough away to enjoy nature. The cottage was clean, easy to find, and exactly as described.
    We decided to take the wine/beer tour offered in the description, it was great! Billy, our driver/host, was friendly, knowledgeable, and seemed VERY excited to have us.

    Robert

    Aug '2023

  • We had a lovely stay. Only an hour to some of Shenandoahs best hikes and 20 minutes to Charlottesville. As advertised. We would absolutely stay again. Thanks for everything!

    Mike

    Aug '2023

  • Always the go to spot for my girlfriend and I and another couple to escape the city. Wine tours they provide are top notch and I just can’t say enough about this place and the owners on my 5th and definitely not last time here.

    Dan

    Aug '2023

  • We had a wonderful stay! It was such a peaceful and beautiful location! It was so nice to be able to book their driver/van for our wine tasting as well.

    Jennifer

    Jul '2023

  • Peaceful gorgeous scenery and setting. Cozy two bedroom cabin. Loved sitting on the cabin’s deck hearing nothing at all watching the deer roam about. Enjoyed walking up to view the sunset while sitting on the Adirondack chairs up on the hill. Highly recommend visiting.

    Rebecca

    Jun '2023

  • We had a delightful stay at the Cabin. It is very cozy having everything one needs and is a wonderful place to disconnect, be saturated in nature, surrounded with awesome views. Great location, too – close enough to Charlottesville and surrounding area while also being exceptionally remote.

    Bill

    May '2023

  • Amazing cabin because it was so peaceful and quiet, I had the best sleep I’ve had in forever!

    Courtney

    May '2023

  • Our cottage had everything we needed. The property is beautiful with Shennandoah national park as a backdrop. Wildlife was plentiful and we enjoyed the evenings watching the deer on the hillside. We even spotted a fox on two occasions. Perfect location to getaway and unwind!

    David

    Apr '2023

  • If you’re looking for a peaceful, quiet, and remote getaway, look no further. We loved our stay here and wished we could have spent more time. The sunset over the mountain is unmatched. Highly recommend.

    Kate

    Apr '2023

  • The place was nice, cozy and clean. Near hiking and vinyards/breweries.

    We opted for the vineyard tour and so glad we did. Bill is very knowledgeable about the surrounding area and shared a lot of history and information with us along our tour. We enjoyed it very much.

    We will definitely be back. We would 100% recommend staying here. You’ll be glad you did.

    Bee

    Mar '2023