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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Wintergreen and around

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, (35)
"The Ivy Rose Cottage was very comfortable and creatively decorated. The kitchen is nicely supplied for cooking simple meals. The trains did not disturb us and were fun to watch, especially the Amtrak. Great pizza and local brewery in nearby Crozet plus an excellent Harris Teeter grocery. Highly recommend this location for anyone looking for an out-of-town stay. "
The price is €253
includes taxes & fees
20 Aug - 21 Aug
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, (137)
"Beautiful property. Great placee to rest and relax."
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (55)
"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!
Mechum Hill Cottage: Central to Crozet & Cville
Outdoor dining

Mechum Hill Cottage: Central to Crozet & Cville

9.4 out of 10, Exceptional, (12)
"The location and very clean cottage"
The price is €246
includes taxes & fees
17 Aug - 18 Aug
Mechum Hill Cottage: Central to Crozet & Cville
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 €407
includes taxes & fees
25 Aug - 26 Aug
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Quiet Blue Ridge Mountain Cottage
Outdoor dining

Quiet Blue Ridge Mountain Cottage

9.6 out of 10, Exceptional, (88)
"small, quaint little cottage that accommodated our lodging needs sufficiently"
Quiet Blue Ridge Mountain Cottage
Birds and Bees Cottage
Fridge, microwave, oven, stovetop

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
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 €292
includes taxes & fees
17 Aug - 18 Aug
High Street | Walk to Everything Crozet | Pet-Friendly
The Firefly Cottage
Fridge, microwave, oven, stovetop

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
Isolated cottage with good view close to many winery and Brewers.
Exterior

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is €228
includes taxes & fees
18 Aug - 19 Aug
Isolated cottage with good view close to many winery and Brewers.
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
Interior

Brand new serene luxury cottage just off the Brew Ridge Trail

The price is €140
includes taxes & fees
18 Aug - 19 Aug
Brand new serene luxury cottage just off the Brew Ridge Trail
"The Sparrow" at Historic Downtown Staunton
Fridge, microwave, oven, stovetop

"The Sparrow" at Historic Downtown Staunton

9.8 out of 10, Exceptional, (16)
"Spent my 60th birthday here with my best friend! Awesome trip! "
"The Sparrow" at Historic Downtown Staunton
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Fridge, microwave, coffee/tea maker, toaster

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
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Terrace/patio

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

9.8 out of 10, Exceptional, (8)
"Very quiet and peaceful. Perfect for a couples getaway :) "
The price is €279
includes taxes & fees
17 Aug - 18 Aug
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Peaceful Raphine Cottage w/ Deck & Fireplace!
TV, fireplace

Peaceful Raphine Cottage w/ Deck & Fireplace!

9.8 out of 10, Exceptional, (15)
"We had a great time, beautiful home and gorgeous scenery!"
Peaceful Raphine Cottage w/ Deck & Fireplace!
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Pool

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (25)
"We had a great time!! The house was spotless, hot tub was great, and the fire pit was perfect! We had fun playing pool every night and seeing the animals next door during the day. Master bedroom and bathroom are amazing!!!"
The price is €541
includes taxes & fees
18 Aug - 19 Aug
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Cozy Cottage at Frogmorton
Fridge, microwave, oven, stovetop

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 €181
includes taxes & fees
17 Aug - 18 Aug
Cozy Cottage at Frogmorton
Charming Mountain Escape | Hot Tub & Scenic Views
Fridge, microwave, oven, stovetop

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
Serene Roseland Retreat Near Wintergreen Resort!
House (3 Bedrooms) | Front of property

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

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

10/10 Excellent
"Ideal stay - wish I’d stayed longer than one night"
Helen 1-night trip
Posted 3 days ago
The Blackburn Inn and Conference Center

Frequently asked questions

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What is there to do in Wintergreen near my cottage?
Once you've checked in to your hotel, venture out and discover the fantastic things Wintergreen has to offer. Wintergreen Resort is a top attraction to add to your travel itinerary.