Book Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Roseland
The price is AU$626 per night from 14 Jan to 15 Jan
AU$626
includes taxes & fees
14 Jan - 15 Jan
When you stay at this vacation home in Wintergreen, you'll be on a lake, just steps from Wintergreen Resort and George Washington National Forest.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Fantastic Mountain & Valley Views!  Top of the Mountain & Close to the Resort!

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Roseland
When you stay at this vacation home in Wintergreen, you'll be in the mountains, just steps from Wintergreen Resort and George Washington National Forest.
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
White Rock Cabin

White Rock Cabin

Montebello
Located in Montebello, this vacation home is in a rural location, a 1-minute drive from George Washington National Forest and 9 minutes from Priest ...
White Rock Cabin
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Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

Wintergreen Resort
With a stay at this vacation home in Wintergreen (Treeloft), you'll be steps from Wintergreen Resort and George Washington National Forest.
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly

Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly

Wintergreen Resort
When you stay at this vacation home in Nellysford, you'll be in the mountains, within a 10-minute walk of Wintergreen Resort and George Washington National ...
Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly
COZY SKI COTTAGE--SKI IN SKI OUT

COZY SKI COTTAGE--SKI IN SKI OUT

Roseland
With a stay at this vacation home in Wintergreen (Pedlars Edge), you'll be steps from Wintergreen Resort and George Washington National Forest.
COZY SKI COTTAGE--SKI IN SKI OUT
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!

Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!

Wintergreen Resort
The price is AU$1,673 per night from 12 Jan to 13 Jan
AU$1,673
includes taxes & fees
12 Jan - 13 Jan
With a stay at this vacation home in Wintergreen (Treeloft), you'll be steps from Wintergreen Resort and George Washington National Forest.
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

Wintergreen Resort
With a stay at this vacation home in Roseland (Chestnut Springs), you'll be within a 15-minute walk of Wintergreen Resort and George Washington National ...
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome

Roseland
The price is AU$1,212 per night from 6 Jan to 7 Jan
AU$1,212
includes taxes & fees
6 Jan - 7 Jan
With a stay at this vacation home in Nellysford (Chestnut Springs), you'll be steps from Wintergreen Resort and George Washington National Forest.
4 BR cabin mins to trails & breweries pets welcome
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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.

Greenwood Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greenwood vacation homes are the perfect way for you to wing it.

Holiday houses in Greenwood let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greenwood in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greenwood adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greenwood with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greenwood vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Greenwood Holiday Homes essential information

Accommodation
442 Holiday Homes
Lowest Price
AU$96
Highest Price
AU$1,673
Popular accommodation
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House., Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!, White Rock Cabin, Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!, Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly, COZY SKI COTTAGE--SKI IN SKI OUT, Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!, Mountain Chalet – Panoramic Views of Blue Ridge Mountains!, 4 BR cabin mins to trails & breweries pets welcome

Top trending hotels in Greenwood

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 5 Jan to 6 Jan
AU$174
includes taxes & fees
5 Jan - 6 Jan
With a stay at English Inn of Charlottesville in Charlottesville (The Meadows), you'll be within a 15-minute drive of University of Virginia and Monticello.
English Inn of Charlottesville
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
212 Ridge McIntire Rd, Charlottesville, VA
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 23 Jan to 24 Jan
AU$272
includes taxes & fees
23 Jan - 24 Jan
With a stay at Omni Charlottesville Hotel in Charlottesville (North Downtown), you'll be steps from Downtown Mall and 3 minutes by foot from Paramount ...
Omni Charlottesville Hotel
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
1600 Emmet Street, Charlottesville, VA
Fully refundable
The price is AU$163 per night from 12 Jan to 13 Jan
AU$163
includes taxes & fees
12 Jan - 13 Jan
With a stay at Country Inn & Suites by Radisson, Charlottesville-UVA, VA in Charlottesville (The Meadows), you'll be within a 15-minute drive of University of ...
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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Motel 6 Staunton, VA

Motel 6 Staunton, VA

2 out of 5
96 Baker Lane, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is AU$96 per night from 4 Jan to 5 Jan
AU$96
includes taxes & fees
4 Jan - 5 Jan
Located in Staunton, Motel 6 Staunton, VA is a 4-minute drive from Factory Antique Mall and 7 minutes from Frontier Culture Museum.
Motel 6 Staunton, VA
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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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^Subject to availability and chosen travel dates.