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$619 per night from 12 Feb to 13 Feb
AU$619
includes taxes & fees
12 Feb - 13 Feb
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.
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!
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Wintergreen Resort
With a stay at this vacation home in Nellysford (Deer Springs), you'll be within a 10-minute walk of Wintergreen Resort and George Washington National ...
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
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 Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort Post & Beam Home Beauty

Wintergreen Resort
With a stay at this vacation home in Roseland (Laurel Ridge), you'll be within a 5-minute drive of Wintergreen Resort and George Washington National Forest.
Wintergreen Resort Post & Beam Home Beauty
Hilltop Escape At Wintergreen

Hilltop Escape At Wintergreen

2 out of 5
Wintergreen Resort
With a stay at this vacation home in Nellysford (Chestnut Springs), you'll be within a 5-minute drive of Wintergreen Resort and George Washington National ...
Hilltop Escape At Wintergreen
Historic Beauty and Walkable to Everywhere

Historic Beauty and Walkable to Everywhere

Charlottesville
The price is AU$361 per night from 12 Feb to 13 Feb
AU$361
includes taxes & fees
12 Feb - 13 Feb
A stay at this vacation home places you in the heart of Charlottesville, just a 5-minute walk from Downtown Mall and within a 5-minute drive of University of ...
Historic Beauty and Walkable to Everywhere
Boutique Room steps from Downtown Mall | Rose Jean - Room #3

Boutique Room steps from Downtown Mall | Rose Jean - Room #3

Charlottesville
The price is AU$326 per night from 12 Feb to 13 Feb
AU$326
includes taxes & fees
12 Feb - 13 Feb
With a stay at this vacation home, you'll be centrally located in Charlottesville, steps from Downtown Mall and within a 5-minute drive of University of Virginia ...
Boutique Room steps from Downtown Mall | Rose Jean - Room #3
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Roseland
When you stay at this vacation home in Wintergreen, you'll be on a river, just steps from Wintergreen Resort and George Washington National Forest.
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
Charming Updated 3 Bedroom Home Near Downtown

Charming Updated 3 Bedroom Home Near Downtown

Charlottesville
The price is AU$759 per night from 16 Feb to 17 Feb
AU$759
includes taxes & fees
16 Feb - 17 Feb
With a stay at this vacation home, you'll be centrally located in Charlottesville, a 2-minute drive from Downtown Mall and 6 minutes from University of Virginia ...
Charming Updated 3 Bedroom Home Near Downtown
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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
450 Holiday Homes
Lowest Price
AU$103
Highest Price
AU$759
Popular accommodation
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House., Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!, Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort, Wintergreen Resort Post & Beam Home Beauty, Hilltop Escape At Wintergreen, Historic Beauty and Walkable to Everywhere, Boutique Room steps from Downtown Mall | Rose Jean - Room #3, Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK, Charming Updated 3 Bedroom Home Near Downtown

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$179 per night from 18 Feb to 19 Feb
AU$179
includes taxes & fees
18 Feb - 19 Feb
With a stay at English Inn of Charlottesville in Charlottesville (The Meadows), you'll be within a 5-minute drive of University of Virginia and University of ...
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$283 per night from 23 Feb to 24 Feb
AU$283
includes taxes & fees
23 Feb - 24 Feb
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
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$103 per night from 12 Feb to 13 Feb
AU$103
includes taxes & fees
12 Feb - 13 Feb
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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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$179 per night from 14 Feb to 15 Feb
AU$179
includes taxes & fees
14 Feb - 15 Feb
With a stay at Country Inn & Suites by Radisson, Charlottesville-UVA, VA in Charlottesville (The Meadows), you'll be within a 5-minute drive of University of ...
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
Don't see what you're looking for?
See all available properties in Greenwood
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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.