We supply the wood
Bailey's Retreat Cottage #1- 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
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.
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. 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 11:30 - 4:00 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.

Indoor fireplace
Laptop friendly workspace

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

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.


183 Reviews

Check In
Courtney User Profile
September 2017
Bailey's Retreat was exactly what we needed. We hit a few wineries on the way up and enjoyed dinner at Duner's before calling it a night. The bed was comfy and the experience was easy and relaxed!

Scott User Profile
September 2017
This is a nice place to get away from it all. Nothing fancy, but a solid, clean cottage with a comfortable bed. The kitchen is small, but complete and a meal could easily be made there. It is nice to have a separate seating area from the bedroom. I wish we had been there longer to try out the outdoor fireplace even to have a fire in the working fireplace in the cabin.

Rebecca User Profile
August 2017
Absolutely lovely Cabin, beautiful views, fresh air - highly recommended.

Karen User Profile
August 2017
Super cosy little cottage with great views. If you love he peace and quiet this is the spot for you. Checkin was super easy and the place was so cosy and we felt immediately at home. We would highly recommend this place to anyone wanting a peaceful getaway.

Christina User Profile
July 2017
My husband and I loved our stay at Baileys cottage. We had perfect view of sunsets and wildlife. We cant wait to come back to this beautiful quiet place.

Bryanna User Profile
July 2017
Super cute little cabin! Had a relaxing time celebrating our 3rd wedding anniversary! Wish we could have stayed longer. Only thing that would have made it PERFECT would be a hot tub/and or pool!

Laly User Profile
July 2017
Beautiful scenic views! Clean and comfortable cottage..can't wait to book all four as a group next time...

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

The neighbourhood

Similar listings