View from kitchenComfortable Pottery Barn pull out sofa.  Second sliding glass door
Bailey's Retreat Cottage #1- WINE/BEER TOUR option
Bailey's Retreat Cottage #1- WINE/BEER TOUR option

Entire home/apt

4 Guests

2 Bedrooms

2 Beds

Please set the number of adults.
Please set the number of children.
Ages 2 - 12
Please set the number of infants.
Under 2
4 guests maximum. Infants don’t count toward the number of guests.
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About this listing

Situated in woodsy area with mountain views this two bedroom cottage is a perfect escape. Enjoy peaceful countryside while being close to wineries, breweries, SNP, and downtown area. You'll have access to pavilion with outdoor Chimney, and lawn terrace for sunset viewing. At Bailey's Retreat we offer four separate cottages, a Farmhouse, and a Cabin expanding over 50 rustic acres. Wedding groups, reunions, please ask about package deals and group rates. Wine/Beer Tours now available $40/person

The space

Perched on 50 rustic acres in Ivy, Virginia, seven miles west of Charlottesville and seven miles east of Crozet, Bailey's Retreat offers scenic serenity for nature lovers, artists, writers, sportsmen or city slickers who simply want to unwind. Or not. Mere minutes from the University of Virginia, Monticello, Skyline Drive, Wintergreen, wineries and breweries, the cottage conveniently sits in the center of regional tourist attractions that fan out in four directions.

This 850 sq foot cottage features a wood burning fireplace, bright sunny living room with sliding glass doors leading to a deck where you can sit and take in natures beauty. There are two bedrooms, one queen and one full. The beds are made up with high quality designer linens and pillows. Fully stocked galley kitchen with Cuisinart cookware and dinnerware.

Relax and enjoy!

Bailey's Retreat now offers wine and beer tours. The wine tours are from 11:00 - 5:00 on Saturdays and Sundays. We hit between 4 and 6 wineries.

Example route:
Pippen Hill
King Family
Cardinal Point

We offer Brewery tours from 5:30-10:00 on Fridays and Saturdays
All the Breweries serve food so you can have dinner.
Devils Backbone
Blue Mountain Brewery
Pro Re Nata Brewery

Light snacks and water are provided in the van.

Cost is $40/person gratuity is not included.

Please let me know if you are interested as we have a limited number of seats.

Please inquire about weekday tours.

Whatever your reason for visiting the area, we'd love to host you at Bailey's Retreat Cottage!

Guest access

We are happy to share much of our retreat with guests. We welcome you to
bring a picnic or a bottle of wine to 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.
Bailey's Retreat is 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.

Interaction with guests

We provide our guests with privacy yet ample support if need be.

Business travel
   This listing has essential business travel amenities. 

The space
Accommodates: 4
Bathrooms: 1
Bedrooms: 2
Beds: 2
Check In: Anytime after 3PM
Check Out: 11AM
Room type: Entire home/apt
Self check-in: Lockbox


Extra people: $30 / night after 2 guests
Cleaning Fee: $40
Weekend Price: $130 / night
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House Rules
No smoking
Not suitable for pets
No parties or events
Check in is anytime after 3PM

Thanks for your attention to the rules.
Please be courteous and understand your surroundings. The Retreat is a peaceful place to which you are our guests.
No pets, no exceptions!!
Kids are people too, all individuals are to be counted as guests.
If you would like to check in early or stay late please contact me to make arrangements. There is a $40 charge.
Check out is promptly at 11:00.
NO smoking inside the properties
You are our guests, please do not invite anyone to the Retreat. The only people allowed on the property are the guests on the reservation. If you'd like to meet friends or family please do so off site.
No grills
There are check out procedures in the brown folder on the table and a digital copy emailed two days prior to your arrival, and here (below) ; if they are not followed you'll be charge an additional fee. Thanks in advance for your cleanliness.
Any violation to these rules and you will be asked to leave.

Turn thermostat to the OFF position
Put dishes in dishwasher and press start
Remove all food from refrigerator. Feel free to leave usable condiments for next guests.
Strip beds and place soiled linens and towels in laundry basket.
Return keys to lockbox, leave door unlocked.
Take garbage to large green cans on your way out.



Cancel up to 7 days before your trip and get a 50% refund plus service fees back.

Safety features
Smoke detector
Carbon monoxide detector

1 night minimum stay

173 Reviews

Check In
Corrine User Profile
June 2017
This place was perfect! We booked it for my friend and I to meet half way for a girl's weekend getaway and it delivered exactly what we were looking for. It was easy to get to even though it felt far away from everything. It was peaceful and quiet and it was so relaxing to sit outside and watch the deer run through the backyard and listen to the bullfrogs. They had the comfiest beds and a great couch to stay up late sitting on while we talked and drank wine. We were able to make it to 4 wineries in one day and then picked up pizza on our way back. Kitchen had everything we needed for our weekend and they even left a few snacks for us, including homemade banana bread that was to die for. Will definitely be back for sure!

Jennie User Profile
June 2017
My boyfriend and I loved our short stay at Bailey's retreat. The cottage was exactly as described and provided a great haven away from busy DC life. The cottage lacked nothing and was clean with just enough space and amenities for our stay. We enjoyed a bottle of wine on top of the ridge while watching the sunset, relaxing, and breathing in the country air. We are already talking about coming back sometime in the near future. Highly recommend! Thanks Roseanne and Bill!

Lorraine User Profile
May 2017
Everything you need for a quiet and peaceful get Away.

Noorah User Profile
May 2017
Very cool, very nice, very tiptop. A+. Just for future renters, they didn't have a laundry machine but they have laundry service for more than one day. It wasn't an issue though. We actually got to meet Bill, great person. He explained to us the history of the place and drove us from the outdoor fireplace back to the house, which was my first time riding in the back of a pick up truck

Brian User Profile
May 2017
What a beautiful, well kept cottage. Roseanne and Bill were great hosts and the property was fantastic. Only issue we had was that we were short a few towels, contacted Roseanne while we were out in Cville and they were at the cottage when we got back. Great service, beautiful property! Can't wait to come back!

Ethan User Profile
May 2017
Well appointed cottage on a beautiful scenic hillside - it was a perfect place to relax between our two day trip. We would've enjoyed staying a second night or more and exploring the area! A fun surprise was the locally sourced and delicious pumpkin bread - had it for dessert and breakfast!

Barbara User Profile
May 2017
Nicely secluded clean and very homey accommodations. No TV which was fine for us. Good internet though. Thoroughly enjoyed our 4 night stay.

This host has 798 reviews for other properties.

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Charlottesville, Virginia, United States · Joined in April 2013
Roseanne & Bill User ProfileRoseanne & Bill is a superhost.

We are Roseanne and Bill Bailey, proprietors of this side of the mountain that's been in our family for more than a century. We live, with our two children, on the Retreat. Considerate hosts, we strive to provide privacy, yet sufficient support to make your stay comfortable. We are thrilled to share our scenic and peaceful playground. Please let us know if you have any questions at all, we're happy to correspond. .

Response rate: 100%
Response time: within an hour
Exact location information is provided after a booking is confirmed.