A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Check availability on Wintergreen Luxury Hotels

Tonight
28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Wintergreen luxury hotels

A gravel path leading to a large house surrounded by lush greenery and white hydrangea bushes.
A sign for Crossroads Inn with a date of establishment and address.
A covered porch with white railings, brick walls, and hanging planters.
A staircase with wooden railings and a chandelier above.

1. The Crossroads Inn

The Crossroads Inn
North Garden
  • Experience refined luxury at this mountain bed & breakfast with an attached winery.
₹17,717
₹20,251 total
includes taxes & fees
29 Sept - 30 Sept
The Crossroads Inn
A wooden porch with two rocking chairs and a white fence.
A spacious kitchen with a central island, a dining area, and a fireplace.
A two-story white house with a central entrance, columns, and a symmetrical facade.
A rural property with a wooden fence, a small shed, and a gravel path leading to a gate.

2. The Farmhouse at Veritas

The Farmhouse at Veritas
Afton
  • Mountain retreat nestled in the vineyard offers luxury escape with fine dining options.
₹29,896
₹37,406 total
includes taxes & fees
30 Sept - 1 Oct
The Farmhouse at Veritas
A spacious living room with a stone fireplace, large windows, and a high ceiling.
A wooden deck with a hot tub, outdoor seating, and large windows offering a forest view.
A spacious room with large windows, a wooden deck, and a view of trees.
A large, multi-story building surrounded by dense forest, with a spacious driveway and a small parking area.

3. Iris Inn and Cabins

Iris Inn and Cabins
Waynesboro
₹36,100
₹40,179 total
includes taxes & fees
30 Sept - 1 Oct
Iris Inn and Cabins
A spacious living room with a stone fireplace, wooden ceiling beams, and a dining area with brown chairs.
Wooden barrels arranged outdoors with a white building in the background.
A modern living room with a fireplace, a TV mounted on the wall, and a dining area.
A living room with a fireplace, a sofa, a glass coffee table, and a TV mounted on the wall.

4. Batten Green Venue & Lodging

Batten Green Venue & Lodging
Staunton
  • Luxurious country inn retreat with memory foam beds and beautiful grounds creates peaceful escape near cultural attractions.
₹11,959
₹15,110 total
includes taxes & fees
29 Sept - 30 Sept
Batten Green Venue & Lodging
A large two-story house with a wrap-around porch, multiple windows, and a chimney.
A room with a white door, a wooden floor, a round table with chairs, and a hanging light fixture.
A dining area with a round table, two upholstered chairs, a hanging light fixture, and a fireplace with a brick surround.
A spacious bedroom with a large bed, a fireplace, a sofa, and a television.

5. The Historic Berkeley Place

The Historic Berkeley Place
Staunton
₹12,361
₹19,205 total
includes taxes & fees
29 Sept - 30 Sept
The Historic Berkeley Place
A spacious room with a large window, a round table with a lace tablecloth, and a chandelier.
A wooden deck with a table and chairs, surrounded by trees.
A bedroom with a large bed, a ceiling fan, and a view of the outdoors through the windows.
A large, two-story building with a symmetrical facade, a central entrance with steps, and a flagpole.

6. Steeles Tavern Manor

Steeles Tavern Manor
Raphine
₹24,985
₹28,807 total
includes taxes & fees
12 Oct - 13 Oct
Steeles Tavern Manor
A balcony with a table set for a meal, two chairs, and a scenic view of a vineyard.
A rectangular pool with a stone border, surrounded by a patio area with outdoor furniture and umbrellas.
A wooden chair in a grassy area with trees and a fence in the background.
A dining room with a large wooden table surrounded by chairs, a patterned rug, and a painting on the wall.

7. Woodville Bed and Breakfast

Woodville Bed and Breakfast
Esmont
  • Indulge in rural elegance at this Esmont B&B with an attached winery and seasonal pool.
₹23,621
₹26,999 total
includes taxes & fees
28 Oct - 29 Oct
Woodville Bed and Breakfast
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Top Wintergreen Hotel Reviews

Frequently asked questions

Are you looking for a luxury hotel for your stay in Wintergreen?
Expedia can help you get a flight to Weyers Cave, VA (SHD-Shenandoah Valley Regional) airport or Charlottesville, VA (CHO-Charlottesville-Albemarle) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a trip, so we make it easy to get what you need to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Wintergreen has to offer. Wintergreen has some interesting things to see and do including Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort, so you might want to take in the local sights during your visit.
When can I expect good weather in Wintergreen?
Planning for the weather is an important factor for making your trip to Wintergreen a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Wintergreen is 1228 mm.
What's there to see and do in Wintergreen?
When you're in Wintergreen, enjoy exploring the sights and attractions here including Bold Rock Hard Cider Nellysford Cidery, Wintergreen Resort and Raven's Roost Overlook. If you have a little extra time during your trip, you might want to check out George Washington National Forest and Stoney Creek Golf Course.

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