Greenwood Holiday Rentals : Search Short-Term Rentals

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Holiday Rentals in Greenwood

"We really appreciate the cleanliness and location of this property! We had a great stay and look forward to returning! Ps love the art!! "

includes taxes & fees

13 Feb - 14 Feb

Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio

"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. "

includes taxes & fees

17 Feb - 18 Feb

"This home was everything we needed. Large pantry for storing food, well stocked kitchen supplies, outdoor areas to sit and relax, several sleeping options. The 2 floors gave us privacy and space, yet the closeness for a family or 2 if traveling with friends. Scott is very responsive to any questions or needs. "

includes taxes & fees

19 Feb - 20 Feb

"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)"

includes taxes & fees

17 Feb - 18 Feb

"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...

"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. "

includes taxes & fees

10 Mar - 11 Mar

"My family needed a place to stay at Wintergreen due to their being a very large group of us. We have a condo on the mountain, so are very use to all the ins/outs of the resort. Not only is the condo one of the best equipped I have seen on the mountain, it is for sure the cleanest we have ever stayed in. Communication with the host was excellent and accommodating. This is an excellent choice for just an overnight stay or week! When we are in need of a unit at Wintergreen, we will be going back...

includes taxes & fees

18 Feb - 19 Feb

"Stayed here while skiing at Massanutten for the weekend! Great distance with scenic views on the drive to and from the mountain. We enjoyed the convenience of the full kitchen, TV, spa shower, and heating system to keep us relaxed after long days of skiing. The sleep number bed in the front bedroom is incredibly comfortable! All appliances worked perfectly and were very helpful in making our stay easy and enjoyable. Will definitely visit again!"

includes taxes & fees

13 Feb - 14 Feb

"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. "

"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...

"Nice property, great location, good communication with owner management."

"Heather’s place was cozy, well-stocked with every detail considered. Heather was communicative and helpful. Great stay."

"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."

"Great property and host! "

"Well stocked kitchen, , clean, firewood provided, close to mountain!! would come back again"

includes taxes & fees

13 Feb - 14 Feb

"This is a great find for this area. Very nicely appointed, felt comfortable and safe. Would stay again. "

includes taxes & fees

13 Feb - 14 Feb

"A clean and charming stay a short walk from downtown. Really enjoyed our stay."

includes taxes & fees

13 Feb - 14 Feb

"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "

"Beautiful area and beautiful home."

"Our stay at this incredible mountain home in Wintergreen Resort was nothing short of spectacular! From the moment we arrived, we were blown away by the breathtaking views and the warm, welcoming atmosphere of the house. Every detail was thoughtfully designed to provide both comfort and luxury, making it the perfect setting for our long-overdue family reunion. With seven beautifully appointed bedrooms, each family had their own space while still enjoying the togetherness we were craving after a...

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"I enjoy our stay for 4 nights for a family wedding at English Inn , clean, decent and breakfast is always good and staff are friendly ,plus Budo bagels is just in front, a must try delicious 👌 :) "

includes taxes & fees

16 Feb - 17 Feb

"Everything was great and clean."

includes taxes & fees

23 Feb - 24 Feb

"I like the area, its quite and housekeeping always ask if i need things, i clean my own room and its your room they do not enter it so its not a bad place "

includes taxes & fees

13 Feb - 14 Feb

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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Holiday Rentals in Greenwood

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Check prices for these dates

Holiday Rentals in Greenwood

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

Love Ridge Mountain Lodging

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

Valley Extended Suites

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

Ivy Rose Cottage nestled b/t Cville & Vineyards

Endless Mountain Top Views from All The Way Up!

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

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

The newest and largest edition to the Wintergreen Retreat portfolio!

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

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

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

View from the Top

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

Welcome to the daughter of the stars

Historic Beauty and Walkable to Everywhere

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

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

Insane Mountain Views - New Listing

Other types of properties in Greenwood you may be interested in

English Inn of Charlottesville

Omni Charlottesville Hotel

Motel 6 Staunton, VA

Find out more about Greenwood

Frequently asked questions