Escape to the Vineyards: Where Relaxation Meets Discovery

Discover a handpicked collection of vacation rentals and inns nestled in Virginia’s wine country — where the pace slows, the views stretch for miles, and every day invites a new kind of joy. Whether you’re a wine enthusiast eager to sip your way through award-winning wineries or simply seeking a serene escape, these properties offer the perfect home base.

Set on or just minutes from some of the region’s most celebrated vineyards, each home provides an ideal mix of comfort and character. Think charming cottages with panoramic views, or spacious retreats built for memory-making with family and friends. Spend your days savoring local vintages, wandering through storybook small towns, or unwinding on a private patio as the sun dips behind the vines. These vineyard stays aren’t just places to rest — they’re destinations in their own right.

Colle

Historic Estate w/ land granted by Jefferson & where the first wine grapes were planted in 1773. Today, wine culture flows strong as the home of Jefferson Vineyards.

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The Crossroads Inn

Crossroads Inn has been accommodating travelers since it was built in 1820 and is listed on the National Historic Register as a designated Virginia Historic Landmark. In 2022, the Inn was purchased by the owners of longtime neighbors, Pippin Hill Farm & Vineyards. Dean and Lynn Andrews built Pippin Hill in 2010 as part of their growing brand, The Easton Porter Group. With a passion and successful history of restoring historic inns, Dean and Lynn purchased the Crossroads Inn to carry on its historic legacy through the elevated and curated Easton Porter lens.

Aftonshire

Located in the heart of Nelson County’s 151 Trail at the foot of the Blue Ridge Mountains, Aftonshire Cottage is a beautifully renovated space to meet all your traveling needs. Whether you plan to tour the vineyards, hop the breweries, hike the mountain trails or ski Wintergreen this charming cottage will be a welcoming base camp you’ll enjoy returning to again and again. Enjoy dining on the outdoor deck and relaxing in the open plan living area.

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Keelona Cottage

Newly remodeled! This peaceful cottage is located behind the main house on the property and affords guests complete privacy. The welcoming covered front porch and the expansive deck that wraps the entire back of the cottage and around one side has multiple seating areas for you to enjoy nature at her finest! The property overlooks the pastures, your closest neighbors will be the resident horses – or maybe even a zebra! Fully furnished with two bedrooms with king beds and 2 full baths.

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River Meadows Farm

River Meadows Farm is a magical farm of 39 acres, with mountain views, walking trails, wild flower meadows, orchards, pastures, and the Lynch River flowing through. There is a swimming pool and poolhouse nestled in a beautiful setting and a swimming hole in the river, which is also a fun place to fish. It is close to multiple vineyards along the Monticello Wine Trail, as well as, Charlottesville/UVA, mountain hikes and Skyline Drive. Barns, cabins, outdoor eating areas, fire pits, an old rock quarry – it is a wonderful place to get away. The main house is a beautiful restored old-Virginia 4 bedroom. There are 3 bedrooms upstairs, a queen murphy bed in the library and a king bed in the bedroom in the basement.

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Reviews

What people are saying about their time with us.

5.0

“Our family had a wonderful experience with Monticello Wine Tour and Coach Co. They were consistently on time, delivered us to all the scheduled stops, and never missed a beat. Our driver, Latisha, was gracious, welcoming, and communicated ...”

4 months ago

“We had such a great experience with Monticello Wine Tours! Our group of 11 had the best day visiting 3 wineries. Our driver, Ali, was wonderful - so friendly, professional, and made sure everyone was safe. Pickups were timely, coordination ...”

Payton Jager

4 months ago

“I went to Charlottesville for a weekend girls trip and used Monticello Wine Tour & Coach Co to help plan the itinerary and transportation.”

Rene Alford

a month ago

“I hired Monticello wine tours for my daughter's 21st birthday celebration and the whole experience was absolutely incredible. Joe was their driver and he was amazing from start to finish making sure everyone arrived at each winery on time and was just an absolute pleasure. I cannot recommend Monticello wine tours enough!!!”

danielle wayne

2 weeks ago

“This was a great experience from Lisa with scheduling, to Melissa with planning and Joe the day of the event. It was truly seamless even with the storm! Melissa kept me updated and was very optimistic. It was 10 adults in this trio and we all enjoyed ourselves and would do it again!”

Pa'Trika Thornton-Henderson

2 months ago

“Highly recommend booking! We had a wonderful experience for a bachelorette party and Monticello Wine Tour took all of the stress of planning/coordination away. Melissa (planner) and Latisha (driver) were both so helpful and friendly. This was money well spent for the value!”

Ashley Riordan

7 months ago

“So much fun! This was the only tour that would pick us up from Wintergreen Resort Area and it was perfect! The people behind the scenes that helped plan the tour were awesome and had great advice. Our tour guide Greg was so fun! This was the perfect tour for our bachelorette party - it really made the trip that much better. Thank you!”

Taylor Wach

4 months ago

“Exceptional experience. Very prompt and helpful. Melissa's custom wine tour itinerary delivered an end result of a fun filled day for everyone. Ian, our driver, was very personable and accommodating and made our tour extra special with lots ...”

Kathleen M Davis

4 months ago

“We had a fantastic time with Greg! He made the ride so smooth and simple. Went above and beyond for our large group of 11. Would highly recommend!”

Susan Youngsteadt