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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Featured Cottages in Wintergreen

Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (38)
"Perfect location for winery, golf, dining and shopping in the Crozet and Charlottesville area. I would definitely recommend and consider staying here again."
The price is AU$465
includes taxes & fees
2 Sept - 3 Sept
Unique Cypress cottage, close to Charlottesville with mountain views.
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Exterior

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

9.8 out of 10, Exceptional, (140)
"This was our fourth visit and we love the house, the property and the area. We are already booked for next year "
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
The Firefly Cottage
Exterior

The Firefly Cottage

10.0 out of 10, Exceptional, (43)
"Firefly Cottage was a charming escape—lush greenery, diverse surroundings, and serene farm views made it unforgettable. We thoroughly enjoyed our time in this peaceful haven, filled with beauty and variety."
The Firefly Cottage
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

10.0 out of 10, Exceptional, (19)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is AU$700
includes taxes & fees
8 Sept - 9 Sept
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
High Street | Walk to Everything Crozet | Pet-Friendly
Terrace/patio

High Street | Walk to Everything Crozet | Pet-Friendly

9.8 out of 10, Exceptional, (101)
"Very cute and very clean. Enjoyed our stay. I understand the abandoned area will be upgraded, looking forward to seeing the outcome"
The price is AU$515
includes taxes & fees
2 Sept - 3 Sept
High Street | Walk to Everything Crozet | Pet-Friendly
Cozy Cottage at Frogmorton
Property grounds

Cozy Cottage at Frogmorton

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great place to stay out in the countryside. All the details taken care of. "
The price is AU$320
includes taxes & fees
3 Sept - 4 Sept
Cozy Cottage at Frogmorton
"The Sparrow" at Historic Downtown Staunton
Outdoor dining

"The Sparrow" at Historic Downtown Staunton

9.8 out of 10, Exceptional, (17)
"Spent my 60th birthday here with my best friend! Awesome trip! "
"The Sparrow" at Historic Downtown Staunton
Birds and Bees Cottage
Terrace/patio

Birds and Bees Cottage

10.0 out of 10, Exceptional, (44)
"Lovely little cottage in the country. Perfect porch for sipping coffee in the morning or watching to sunset. Close to wineries, breweries, hiking and not far from Charlottesville! We enjoyed sitting around the fire pit in the Adirondack chairs. "
Birds and Bees Cottage
The Cottage @ Afton Mountain- Close to Wineries!
Outdoor dining

The Cottage @ Afton Mountain- Close to Wineries!

10.0 out of 10, Exceptional, (14)
"Great place"
The price is AU$524
includes taxes & fees
2 Sept - 3 Sept
The Cottage @ Afton Mountain- Close to Wineries!
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Exterior

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (57)
"We all loved the cottage in Alhambra. The setting was amazing and peaceful tucked in among the mountains and overlooking the creek. The inside was lovely and our hosts had the place outfitted to fill all of our needs. This was one of our favorite stays!"
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Exterior

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (48)
"Very peaceful and comfortable place to stay."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Property grounds

Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

10.0 out of 10, Exceptional, (19)
"We had a great time starting here on spring break."
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Brand new serene luxury cottage just off the Brew Ridge Trail
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

10.0 out of 10, Exceptional, (1)
"Cute, tiny house with everything we could have needed. Perfect location for a weekend touring Nelson County sites. We will be back."
The price is AU$280
includes taxes & fees
2 Sept - 3 Sept
Brand new serene luxury cottage just off the Brew Ridge Trail
Bluebird Cottage: Near 151 + Appalachian Trail
Terrace/patio

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
7.8 out of 10, Good, (7)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
The price is AU$450
includes taxes & fees
2 Sept - 3 Sept
Bluebird Cottage: Near 151 + Appalachian Trail
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts
Exterior

Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts

10.0 out of 10, Exceptional, (4)
" Cleanest rental we've ever stayed in and the kitchen was very well stocked."
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Exterior

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (25)
"This house was absolutely perfect for a quiet weekend getaway. "
The price is AU$941
includes taxes & fees
3 Sept - 4 Sept
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Rosé All Day: Wine Country Getaway! Walk to Dining
Exterior

Rosé All Day: Wine Country Getaway! Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (14)
"Just what we needed for a few days away! Great location with plenty of food and activities nearby! "
Rosé All Day: Wine Country Getaway! Walk to Dining
Charming Mountain Escape | Hot Tub & Scenic Views
Outdoor spa tub

Charming Mountain Escape | Hot Tub & Scenic Views

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay! The house is conveniently located near many popular wineries. We absolutely loved the house amenities, including the hot tub and fire pits. Beds were comfortable and kitchen was well stocked with essentials."
Charming Mountain Escape | Hot Tub & Scenic Views
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Exterior

Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!

10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay. The house, as always, is well stocked and clean. Very convenient location."
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Serene Roseland Retreat Near Wintergreen Resort!
House (3 Bedrooms) | Interior

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Find out more about Wintergreen

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
Accommodation
96 Cottages
Lowest Price
AU$280
Highest Price
AU$941

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Frequently asked questions

What is there to do in Wintergreen near my cottage?
The most useful travel accessory is a well-thought-out travel plan. Bold Rock Hard Cider Nellysford Cidery is a great place to kick-start your adventures in Wintergreen.