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Search Wintergreen Cottage Rentals from CA $106

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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Wintergreen Cottages

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, (32)
"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 CA $202
CA $390 total
includes taxes & fees
Aug 20 - Aug 21
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, (136)
"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!
Exterior

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

10.0 out of 10, Exceptional, (54)
"Really cool property on the Piney River. Great fly fishing in the back yard. Tons of outdoor space- house itself is beautiful. Kids enjoyed their spring break hanging outside and fishing. "
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 CA $177
CA $385 total
includes taxes & fees
Aug 10 - Aug 11
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 CA $260
CA $634 total
includes taxes & fees
Aug 10 - Aug 11
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Quiet Blue Ridge Mountain Cottage
Terrace/patio

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
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
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 CA $275
CA $458 total
includes taxes & fees
Aug 10 - Aug 11
High Street | Walk to Everything Crozet | Pet-Friendly
The Firefly Cottage
Exterior

The Firefly Cottage

10.0 out of 10, Exceptional, (42)
"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 CA $247
CA $360 total
includes taxes & fees
Aug 12 - Aug 13
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
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

The price is CA $106
CA $219 total
includes taxes & fees
Aug 18 - Aug 19
Brand new serene luxury cottage just off the Brew Ridge Trail
"The Sparrow" at Historic Downtown Staunton
Outdoor dining

"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
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
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Outdoor dining

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 CA $188
CA $443 total
includes taxes & fees
Aug 10 - Aug 11
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Peaceful Raphine Cottage w/ Deck & Fireplace!
Terrace/patio

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!
Exterior

❤️️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 CA $229
CA $871 total
includes taxes & fees
Aug 10 - Aug 11
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
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 CA $186
CA $284 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Cottage at Frogmorton
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
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

Sleep Inn Staunton

Sleep Inn Staunton

10/10 Excellent
"This was a basic hotel off the highway. It was clean. The staff was great and the bed was extremely comfortable. The coffee and breakfast were very good. "
Elizabeth 1-night trip
Posted 2 days ago
Sleep Inn Staunton