Photo by Karyn Leary

Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (264)
"The location and view were much appreciated and accurate from the website. Communication with the host initially went well as I wondered how equipped the kitchen was. Be prepared to bring your own dishwashing liquid, laundry soap (washer not used), and preferred spices. We made dinner a couple of nights and it was well equipped. There was minimal hand soap and no additional trash bags. The kitchen stove had tomato food stains, and I ended up sweeping which didn't look done. I sent a couple of...
The price is AU$374
includes taxes & fees
19 Mar - 20 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (173)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is AU$186
includes taxes & fees
24 Feb - 25 Feb
Valley Extended Suites

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

9.6 out of 10, Exceptional, (293)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was very nicely set up, clean, and comfortable. The property manager was in constant contact with me to make sure I had everything I needed. I would highly recommend this place to anyone looking for a quiet relaxing escape. "
The price is AU$415
includes taxes & fees
24 Feb - 25 Feb
Love Ridge Mountain Lodging

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

10.0 out of 10, Exceptional, (44)
"This cottage was in a charming location with a creek out back, lovely grounds, and total privacy. We stayed in the late fall; it must be even better in the spring or summer. It is the best-equipped -i.e., amenities - of any place we’ve ever stayed. Comfortably furnished. Nice appliances. Would happily return. "
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (39)
"We spent a fun girls weekend at the cottage. It’s exactly as described. Very cute and cozy. It was just far enough away from the bustle of the city but close enough that driving out to the heart of Charlottesville was only 20 mins away. The beds were comfortable and it had everything you needed. "
The price is AU$562
includes taxes & fees
19 Mar - 20 Mar
Ivy Rose Cottage nestled b/t Cville & Vineyards

RIGHT ON THE ROCKFISH RIVER!Brand New Cabin, Completely Private,Peaceful,Hiking!

10.0 out of 10, Exceptional, (32)
"We chose this property for a girls getaway, and it was exactly what we were looking for. The views were gorgeous even in January! It was easy to see the river from all bedrooms and the living and kitchen areas through big floor to ceiling windows. "
The price is AU$382
includes taxes & fees
20 Feb - 21 Feb
RIGHT ON THE ROCKFISH RIVER!Brand New Cabin, Completely Private,Peaceful,Hiking!

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (234)
"A beautiful historic property and working farm, it was the perfect getaway for some lifelong friends looking to get away. Bill and Cynthia are wonderful hosts and the home has everything you could need. It is very large and can easily accommodate a large family or group event.We were even given samples of maple water from the frees, and farm-fresh eggs! We would definitely stay here again.Thank you Bill and Cynthia for a perfect weekend."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Stadium Hill House

10.0 out of 10, Exceptional, (12)
"Property was great! We were able to uber/lyft downtown easily. The area is beautiful. We enjoyed Charlottesville and would return!"
Stadium Hill House

Ski at nearby Massanutten Just $99/night at Bear Escape Cottage

9.8 out of 10, Exceptional, (89)
"I stayed here for a quick overnight stop during my ski trip and it was perfect for what I needed. I arrived around 8 PM and left by checkout time. The two bedroom unit was spacious and comfortable with my room being well decorated and featuring a huge bathroom. The bed was super comfy, and the vanity was great for getting ready. The only thing I suggest is adding a mirror in the second room as my friend noticed it was a bit lacking and decoration. The shower in my room was large with two shower...
The price is AU$210
includes taxes & fees
20 Feb - 21 Feb
Ski at nearby Massanutten Just $99/night at Bear Escape Cottage

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.4 out of 10, Exceptional, (120)
"Well stocked kitchen, , clean, firewood provided, close to mountain!! would come back again"
The price is AU$383
includes taxes & fees
20 Mar - 21 Mar
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (61)
"Easy in and out. Nicely finished clean place. Super friendly hosts. Great stay!"
The price is AU$540
includes taxes & fees
9 Mar - 10 Mar
Endless Mountain Top Views from All The Way Up!

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Charming Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

10.0 out of 10, Exceptional, (32)
"Such a great cabin and beautiful property. Check-in/out was super simple and the host was great. Instructions were very nicely laid out and we definitely want to come back! "
The price is AU$379
includes taxes & fees
23 Feb - 24 Feb
Charming Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (9)
"Best price and a perfect little condo just a short walk to the ski lifts. An old man, 3 teenagers, and my mini me, truly enjoyed it. It has all you need to cook and chill out after a long day on the slopes. The fireplace with a constant supply of wood was the sugar on top. Thanks for a great stay."
The price is AU$374
includes taxes & fees
20 Mar - 21 Mar
Wintergreen Condo -Steps to Ski and restaurants

Cozy cabin for 2 w/ great mt views & walking trails!

10.0 out of 10, Exceptional, (150)
"The cabin was cute and cozy and the perfect getaway! It was a peaceful and quiet place and we really enjoyed it."
The price is AU$286
includes taxes & fees
25 Feb - 26 Feb
Cozy cabin for 2 w/ great mt views & walking trails!

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (39)
"17 family members stayed for a long holiday weekend and this house was absolutely perfect! The open floor plan on the main floor offered something for everyone! The kitchen is spacious, has every amenity imaginable including two refrigerators. We used the two sided fireplace which kept us toasty and added to the ambiance. The guys loved having the pool table, and the comfy chairs by the window became the perfect spot to sip some wine and watch the snow fall. We loved the rustic mountain...
The newest and largest edition to the Wintergreen Retreat portfolio!

Unwind in Seclusion: Log Cabin retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (11)
"Wife and I were looking for a place away from the hustle that comes with NOVA normally, and especially the weekend of the inauguration. I must say we found the absolute best spot. Nelson county has always been a favorite spot for us to go to, but most of the time we have made day trips. I absolutely love being able to post up for a weekend in a quiet setting and being able to relax. Even the pup enjoys the quiet and are keen to relax next to the stoves. Most places just leave it up to you to...
Unwind in Seclusion: Log Cabin retreat with Wood Burning Stove & Game Table

Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

10.0 out of 10, Exceptional, (196)
"Don't keep looking..... Book your stay here! It's AMAZING! This cabin has stunning views and complete serenity. The Pavilion by the lake just can't be beat....an outdoor OASIS! The hosts are very accommodating, the Christmas decor was beautiful. The cabin itself is cozy and spacious and will have everything you need!"
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

4 BR cabin mins to trails & breweries pets welcome

9.8 out of 10, Exceptional, (21)
"Excellent location, clean, comfortable, would stay again!"
The price is AU$1,062
includes taxes & fees
20 Mar - 21 Mar
4 BR cabin mins to trails & breweries pets welcome
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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Other types of properties in Greenwood you may be interested in

English Inn of Charlottesville

3.0 star property
9.2 out of 10, Wonderful, (2070)
"I loved the English Tudor look of the place. The lounge with the fireplace was a nice touch. The staff was friendly and helpful. "
The price is AU$176
includes taxes & fees
23 Feb - 24 Feb
English Inn of Charlottesville

Omni Charlottesville Hotel

4.0 star property
9.0 out of 10, Wonderful, (1001)
"My stays have always been very pleasant. "
The price is AU$300
includes taxes & fees
16 Mar - 17 Mar
Omni Charlottesville Hotel

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

3.0 star property
9.0 out of 10, Wonderful, (1042)
"Staff is friendly and helpful upon check in. Room and property are clean. Convenient location. Good hot breakfast with many options. "
The price is AU$177
includes taxes & fees
23 Feb - 24 Feb
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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.

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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This holiday home rental outside of Greenwood is located on a lake, and has an outdoor pool, a fireplace 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. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 King Family Vineyards.

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.