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Houses in Wintergreen and Condos – Holiday Lettings - Holiday Rentals Wintergreen

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75 Holiday homes

Wintergreen holiday home rental

Wintergreen house

5 bedrooms • 5 bathrooms • sleeps 12

from £280 / night

£1,958 / week

1 / 39

Wintergreen ski home to rent.

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 6

from £173 / night

£1,207 / week

1 / 29

Holiday home in Wintergreen

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 8

from £175 / night

£1,224 / week

1 / 16

Ski condo to rent in Wintergreen

Wintergreen condo

1 bedroom • 1 bathroom • sleeps 4

from £113 / night

£708 - £825 / week

1 / 25

Holiday apartment in Wintergreen

Wintergreen apartment

2 bedrooms • 1 bathroom • sleeps 4

from £139 / night

£673 / week

1 / 22

Ski apartment to rent in Wintergreen

Wintergreen apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £100 / night

£625 - £712 / week

1 / 19

Holiday home in Wintergreen

Wintergreen house

3 bedrooms • 4 bathrooms • sleeps 8

“Mother/Daughter Weekend” My mother and I stayed here for a weekend away, and we had an amazing time. The house is gorgeous with a huge spacious living room for sitting and relaxing. The backyard deck is also a good place to relax with a glass of wine and a good book. The backyard backs right up to the golf course which provides a good view. The house was very neat and clean when we arrived and almost everything we could possibly need was provided for us. There were plenty of towels, and all the showers had shampoo, conditioner, and bath gel. The close proximity to all the hiking trails were really what did it for me. Not to mention the amazing views. I can't wait to come back for ski season! We had an great and enjoyable experience here and encourage others to do the same! I highly recommend this rental to everyone. :)

from £246 / night

£1,332 / week

1 / 13

Wintergreen ski home to rent.

Wintergreen house

4 bedrooms • 4 bathrooms • sleeps 12

from £331 / night

£2,179 / week

1 / 21

Wintergreen holiday condo rental

Wintergreen condo

3 bedrooms • 3 bathrooms • sleeps 8

from £97 / night

£676 / week

1 / 24

Condo rental in Wintergreen

Wintergreen condo

4 bedrooms • 4 bathrooms • sleeps 8

from £199 / night

£1,387 / week

1 / 24

Holiday condo rental

Wintergreen condo

2 bedrooms • 2 bathrooms • sleeps 6

from £78 / night

£542 / week

1 / 23

Wintergreen holiday home rental

Wintergreen house

5 bedrooms • 4 bathrooms • sleeps 10

from £301 / night

£2,104 / week

1 / 35

Wintergreen holiday home rental

Wintergreen house

4 bedrooms • 3 bathrooms • sleeps 10

from £130 / night

£909 / week

1 / 36

Wintergreen ski cottage to rent.

Wintergreen cottage

3 bedrooms • 2 bathrooms • sleeps 8

from £173 / night

£1,207 / week

1 / 41

Holiday home with shared pool in Wintergreen

Wintergreen house

4 bedrooms • 3 bathrooms • sleeps 12

from £244 / night

£1,708 / week

1 / 28

Holiday cottage with shared pool in Wintergreen

Wintergreen cottage

3 bedrooms • 2 bathrooms • sleeps 6

from £121 / night

£845 / week

1 / 24

Wintergreen holiday home rental

Wintergreen house

1 bedroom • 1 bathroom • sleeps 3

from £104 / night

£729 / week

1 / 32

Holiday home in Wintergreen

Wintergreen house

5 bedrooms • 3 bathrooms • sleeps 11

from £141 / night

£985 / week

1 / 32

Ski condo to rent in Wintergreen

Wintergreen condo

1 bedroom • 1 bathroom • sleeps 4

from £91 / night

£636 / week

1 / 32

Holiday home in Wintergreen

Wintergreen house

4 bedrooms • 3 bathrooms • sleeps 16

from £173 / night

£1,207 / week

1 / 38

Holiday home in Wintergreen

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 10

from £194 / night

£1,352 / week

1 / 26

Holiday cottage in Wintergreen

Wintergreen cottage

3 bedrooms • 4 bathrooms • sleeps 8

from £199 / night

£1,387 / week

1 / 34

Holiday home with shared pool in Wintergreen

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 8

from £151 / night

£1,055 / week

1 / 31

Holiday cottage with shared pool in Wintergreen

Wintergreen cottage

4 bedrooms • 3 bathrooms • sleeps 8

from £181 / night

£1,265 / week

1 / 39

Holiday home in Wintergreen

Wintergreen house

6 bedrooms • 3 bathrooms • sleeps 16

from £224 / night

£1,568 / week

1 / 31

Holiday home in Wintergreen

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 8

from £87 / night

£606 / week

1 / 31

Wintergreen ski home to rent.

Wintergreen house

3 bedrooms • 2 bathrooms • sleeps 10

from £258 / night

£1,807 / week

1 / 38

Holiday home in Wintergreen

Wintergreen house

4 bedrooms • 3 bathrooms • sleeps 9

from £164 / night

£1,143 / week

1 / 28

Wintergreen holiday home rental

Wintergreen house

6 bedrooms • 4 bathrooms • sleeps 12

from £237 / night

£1,655 / week

1 / 45

Wintergreen ski condo to rent.

Wintergreen condo

1 bedroom • 1 bathroom • sleeps 2

from £82 / night

£571 / week

1 / 25

Cottage rental in Wintergreen with shared pool

Wintergreen cottage

5 bedrooms • 5 bathrooms • sleeps 10

from £215 / night

£1,504 / week

1 / 26

Holiday home in Wintergreen

Wintergreen house

3 bedrooms • 3 bathrooms • sleeps 4

from £121 / night

£845 / week

1 / 34

Holiday condo in Wintergreen

Wintergreen condo

2 bedrooms • 2 bathrooms • sleeps 4

from £74 / night

£513 / week

1 / 25

Holiday cottage in Wintergreen

Wintergreen cottage

2 bedrooms • 1 bathroom • sleeps 4

from £82 / night

£571 / week

1 / 36

Holiday home with shared pool, golf nearby in Wintergreen

Wintergreen house

5 bedrooms • 5 bathrooms • sleeps 10

from £219 / night

£1,533 / week

1 / 37

Holiday home with shared pool in Wintergreen

Wintergreen house

4 bedrooms • 2 bathrooms • sleeps 9

from £164 / night

£1,143 / week

1 / 37

Holiday cottage with shared pool in Wintergreen

Wintergreen cottage

4 bedrooms • 2 bathrooms • sleeps 8

from £129 / night

£904 / week

1 / 33

Holiday cottage in Wintergreen

Wintergreen cottage

5 bedrooms • 2 bathrooms • sleeps 10

from £164 / night

£1,143 / week

1 / 36

Holiday condo rental

Wintergreen condo

3 bedrooms • 2 bathrooms • sleeps 6

from £74 / night

£513 / week

1 / 26

Wintergreen holiday cottage rental

Wintergreen cottage

3 bedrooms • 2 bathrooms • sleeps 8

from £155 / night

£1,084 / week

1 / 30

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Wintergreen holidays

Wintergreen, Virginia is busy all year round – there's plenty to do! You can try golfing, skiing, mountain climbing, hiking, biking and pretty much anything else you can think of.

You'll find this idyllic spot on the eastern side of the Blue Ridge Mountains, and be amazed at the spectacular views from your very own Wintergreen holiday rental – get searching on Holiday Lettings, today!

About Wintergreen, Virginia

The area around Wintergreen was once populated by the Tuscarora Indians who lived near the Rockfish and James rivers. The Rockfish River Valley has some spectacular scenery and is well worth visiting.

Nearby Jamestown was the first permanent European settlement in the USA, founded by the British in 1607. Because of this, Wintergreen has lots of history to explore – try heading to one of the museums to find out more!

The food in Wintergreen is a mix of American and European (mainly Italian and French). You can eat a hearty steak, or more delicate seafood and fish. There's something for everyone, including vegans and vegetarians.

The area is also known for brewing delicious craft beers – some of the breweries have been going since colonial times. Try some during your stay.

What to do

At the Wintergreen Resort, there are two golf courses for enthusiasts, Devil's Knob and Stoney Creek. They're a great day out.

If you like walking, go along the Rockfish Valley Loop Trail system, and visit Spruce Creek Park. If you want something a bit more challenging, head up to the Appalachian Trail.

In winter you can go skiing, snowboarding and skate. But pack your thermals, as it can get a bit chilly.

Visit Williamsburg and see how people lived there in previous centuries. The town is a living history museum and is full of beautifully restored 17th and 18th century buildings.

The history of Virginia is closely linked to the Civil War. Visit the Appomattox court house, where General Robert E. Lee formally surrendered to General Ulysses S. Grant.

Go to Bold Rock and sample the delicious ciders. You get an amazing view over Wintergreen, and there's lots of space where dogs and kids can run free.

Lyndhurst, Virginia, is home to Humpback Rocks Visitor Center and Mountain Farm. Go to the top of Humpback Rocks and take in the majestic view.

Top Wintergreen travel tips

The easiest way of getting to Wintergreen is by car. You can fly to Charlottesville Albemarle airport, or to Dulles International Airport (IAD) and take a bus or shuttle service. Rent a car at the airport and drive to Wintergreen.

If you love nature's colours, go to Wintergreen in fall. Before you go, cheque the foliage report from the Department of Forestry. Crabtree Falls, on the Blue Ridge Parkway, is a wonderful place for a picnic.

Pick your own apples and pumpkins and buy butternut squash, cashews sweet potatoes and freshly pressed cider during your stay.

Don't leave the area without visiting Devils Backbone to sample the micro-brews.

Whenever you go to Wintergreen, Virginia, you’ll find plenty of activities to try. You can visit the Civil War battlefields, walk the Rockfish Valley Loop Trail, or go to see the historic buildings of Virginia.

check out Wintergreen holiday rentals here on Holiday Lettings and book your perfect stay.

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