Open concept living/dining roomFireplace open from October - May
Bailey's Retreat Cottage #4-WINE/BEER Tour option
Hosted by Roseanne & Bill
Roseanne & Bill is the host.Roseanne & Bill is a superhost.
4 guests
2 bedrooms
2 beds
1 bath
4 guests
2 bedrooms
2 beds
1 bath
You won’t be charged yet

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. Now offering Wine/Beer Tours $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 Rachel Ray 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.

Whatever your reason is 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.
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.
The 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.

Wireless Internet

Sleeping arrangements
Bedroom 1
1 queen bed
Bedroom 2
1 double bed

House Rules
No smoking
Not suitable for pets
No parties or events
Check in is anytime after 3PM
Check out by 11AM
Self check-in with lockbox

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.


122 Reviews

Check In
Stephanie User Profile
July 2017
Bill and Roseanne's cottage was a perfect country retreat for our family. I stayed for one night with my husband and one year old daughter. We loved the clean, modern decor, the super comfortable bed, and the idyllic country setting. This is a great option if you are looking to be close to Charlottesville, but away from the city itself. The cottage was very close to many wineries (we tried King Family), Skyline Drive and the Blue Ridge Parkway. There is no TV so be sure to bring your own amusements for the evenings! We saw many deer on the property!

Marianne User Profile
July 2017
It really is a retreat. Perfect place to stay if you are looking for peace and quiet. It's close enough to Charlottesville that a trek into town several times a day is easy enough. The hosts contacted us at the beginning of our stay to let us know they are available to assist us.

Calie User Profile
July 2017
Roseanne and Bill's place was beautifully maintained and located in a wonderful area. It was just what we needed to relax and get away for a bit. Thank you so much!

Brandy User Profile
July 2017
I had a great time at Roseanne and Bill's place! It's not far from Charlottesville and some amazing Shenandoah hiking. The cottage itself is kept up well and very comfortable. Roseanne and Bill were great hosts even when I got a little turned around on the way up there - very easy to get in touch with. Would stay here again!

Jeff User Profile
July 2017
This was our second time visiting the cottage. Everything was just as great as last year. If you are looking for a quiet, peaceful place to relax, the entire Retreat is the place for you. We are planning to return next year.

Brittany User Profile
June 2017
The cottage we stayed at really was wonderful. The surrounding scenery and nearby areas were beautiful and peaceful, and we felt very safe the entire time. It's obvious that the hosts care for their guests, as the cottage was perfectly clean. They left a few snacks for us and many nice things were provided, such as wifi. We'd definitely recommend it and we'd love to come again.

Samantha User Profile
June 2017
Gorgeous and clean! Beautiful views and a comfortable cottage. Must visit!!

This host has 939 reviews for other properties.

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Charlottesville, Virginia, United StatesJoined 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. W…
Response rate: 98%
Response time: within an hour

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