Photo by Karyn Leary

Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (151)
"We loved the scenic drive to the property traveling from East on 64. "
The price is NZ$183
includes taxes & fees
17 Jun - 18 Jun
Valley Extended Suites
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (238)
"We were very happy with our stay at this lovely place! It was a wonderful experience and we are looking forward to the next time."
The price is NZ$353
includes taxes & fees
9 Jun - 10 Jun
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
10.0 out of 10, Exceptional, (16)
"Very quaint cottage in the country. Close to Shenandoah park. Beautiful yard and landscaping and by a creek. Host had a generous supply of things in case you forgot your own. Very thoughtful. Enjoyed our stay."
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
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Lovely Wooded Cabin with Numerous Trails On-Site!
10.0 out of 10, Exceptional, (51)
"My husband and I had a lovely stay at the cabin! It was perfect for our anniversary trip. Close enough to Shenandoah National park for hiking yet secluded for the perfect off-grid feel."
Lovely Wooded Cabin with Numerous Trails On-Site!
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
9.6 out of 10, Exceptional, (264)
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot tub was wonderful, the wifi works great (we had one doing online school and one work), and all was just as the listing described. It was a great place to stay for a Liberty University graduation. If...
The price is NZ$668
includes taxes & fees
5 Jun - 6 Jun
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Restored Vintage Airstream at Craft Brewery
9.6 out of 10, Exceptional, (8)
"Cute, wonderful place"
Restored Vintage Airstream at Craft Brewery
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, (218)
"We loved the remoteness and rustic feel of the property/house! Great in accommodating our group of 12 - loved sitting on the front porch and lighting the fire pit. We were there for three nights and we did not watch the tv once - testament to how much fun we were having as a family. We also hiked and walked and visited vineyards, ciders and breweries! All in all, the property/house gave us the perfect platform and environment to have a very memorable 3 nights! Recommend without reservation,...
Restored Double Log Cabin on 400 Mountain Acres
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
10.0 out of 10, Exceptional, (183)
"Great place to stay and have my wedding! Would definitely come back for an anniversary stay!"
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (220)
"Bill and Cynthia are such amazing hosts and the property inside and out exemplifies it. What a great place to stay for some serious rural R&R! The property was very clean. They have thought of everything one would need for a delightful get away. If you forgot anything, just ask and they are sure to help one way or another. The Fresh eggs, courtesy of their chickens, were a treat and the farm animals are such fun…esp Posy, Zoey and Hemingway. We hope to return soon for a longer retreat! Thank you...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (34)
"Great view. Nice place very comfortable furniture. Kitchen well appointed. Liked that wineries and breweries near and dog friendly."
Endless Mountain Top Views from All The Way Up!
View from the Top
10.0 out of 10, Exceptional, (38)
"Beautiful condo that is definitely over the top in accommodations. One of my favorite places to stay at wintergreen."
View from the Top
Quiet Blue Ridge Mountain Cottage
9.6 out of 10, Exceptional, (73)
"Easy in and out."
Quiet Blue Ridge Mountain Cottage
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, (209)
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Rustic Mountain Retreat-Bear Paw
9.8 out of 10, Exceptional, (209)
"Pretty cool spot, cozy and peaceful. Deep enough in the woods to forget about work! Prime location for gravel and road cycling."
Rustic Mountain Retreat-Bear Paw
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, (55)
"We had a lovely stay. The area was gorgeous and the house was comfortable and perfect for our family of 5."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
9.8 out of 10, Exceptional, (66)
"My wife and I had a nice stay with our good friends! The location was centrally located which made it easy to Uber to wineries/restaurants!"
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
Cozy cabin for 2 w/ great mt views & walking trails!
10.0 out of 10, Exceptional, (125)
"The cabin was perfect. The area was great."
The price is NZ$299
includes taxes & fees
24 Jun - 25 Jun
Cozy cabin for 2 w/ great mt views & walking trails!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (272)
"We thoroughly enjoyed our stay at this condo. Quiet neighborhood and very comfortable. Appreciated all the basics offered that other rentals do not such as soap, garbage bags, toilet paper. But the owners went above that and had lotions, specialty soaps, cleaning supplies etc. Well stocked kitchen for cooking. While it was just the two of us we liked that there were games available for families and there was a nook upstairs for kids to get away. Highly recommend and would definitely come visit...
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
RiverFront Country Home with Blue Mountain Views
9.6 out of 10, Exceptional, (11)
"Easy check in and check out process. If you like the country and mountains this is the place. Conveniently located down the street from the gas station a small store/ restaurant and not a far drive from the Shenandoah National Park. The reason we chose this place is because it is dog friendly and near the Shenandoah mountains. We visited the mountains for some day hikes. The house is nicely kept and spacious with a big yard."
The price is NZ$308
includes taxes & fees
5 Jun - 6 Jun
RiverFront Country Home with Blue Mountain Views
Cozy Mountain Cabin
10.0 out of 10, Exceptional, (52)
"Dinner at Devils Backbone brewery which is right around the corner. Breakfast in Waynesboro. Hiking at Panther Falls. Polo match at Kings Family Vineyard. Wedding at Sky Ridge Farm. Toilet on master room level would have been nice but rustic log cabin living at it’s finest with all the amenities!"
The price is NZ$314
includes taxes & fees
5 Jun - 6 Jun
Cozy Mountain Cabin
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See all available properties in Greenwood
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.

Other types of properties in Greenwood you may be interested in

English Inn of Charlottesville
3.0 star property
9.0 out of 10, Wonderful, (1690)
"Did not like the powdered eggs for breakfast! Otherwise, it was the best hotel that we stayed in during a 12 day road trip in which we stayed at a different hotel almost every night."
The price is NZ$183
includes taxes & fees
16 Jun - 17 Jun
English Inn of Charlottesville
Sleep Inn Staunton
2.5 star property
9.2 out of 10, Wonderful, (1012)
"Room was clean & comfortable. Enjoyed the breakfast also"
The price is NZ$160
includes taxes & fees
6 Jun - 7 Jun
Sleep Inn Staunton
Days Inn by Wyndham Charlottesville/University Area
2.0 star property
7.4 out of 10, Good, (1007)
"Good value however the advertised breakfast was not available,"
The price is NZ$137
includes taxes & fees
16 Jun - 17 Jun
Days Inn by Wyndham Charlottesville/University Area
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Greenwood. Seeing all the best attractions is bound to make you fall in love with Greenwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Greenwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as War Fields, or get out into nature at a spot like Shenandoah National Park. In the wider area, you’ll find Pollak Vineyards and Veritas Vineyard and Winery.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.

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