Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
9.8 out of 10, Exceptional, (6 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is NZ$242
includes taxes & fees
25 May - 26 May
Brand new serene luxury cottage just off the Brew Ridge Trail

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
Endless Mountain Top Views from All The Way Up!

Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (51 reviews)
"The cabin was amazing, we will definitely be back. Check in was easy, and the cabin had everything we needed. It was spacious and beautifully constructed."
United States
David K.
The price is NZ$479
includes taxes & fees
18 May - 19 May
Unique Cypress cottage, close to Charlottesville with mountain views.

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (56 reviews)
"Great place to stay during our trip to Crozet. Very clean and spacious suites. Great location."
United States
Tatyana
The price is NZ$147
includes taxes & fees
21 May - 22 May
Affordable Suites of America Waynesboro

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (45 reviews)
"Yes: Very Pleasant and professional Volunteered to allow me to stay longer. Very peaceful stay was able to complete my objective that I went to accomplish "
United States
Issaac P.
The price is NZ$351
includes taxes & fees
13 May - 14 May
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is NZ$468
includes taxes & fees
17 May - 18 May
Laurelwood Hollow: Walk to Ski & Swim

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (103 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is NZ$329
includes taxes & fees
1 June - 2 June
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is NZ$386
includes taxes & fees
20 May - 21 May
Where the Trail Ends

Shenandoah Mansion

Shenandoah Mansion
Elkton
8.8 out of 10, Excellent, (9 reviews)
"The house was amazing and very cozy. My family enjoyed the amenities that come with the property. I would visit again."
United States
Jansenia Diane
The price is NZ$1,982
includes taxes & fees
19 May - 20 May
Shenandoah Mansion

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
The price is NZ$243
includes taxes & fees
21 May - 22 May
SONSAK - MONTICELLO

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is NZ$363
includes taxes & fees
13 May - 14 May
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is NZ$446
includes taxes & fees
18 May - 19 May
Wintergreen Condo -Steps to Ski and restaurants

Shenandoah Valley Atelier: NEW Waynesboro Loft

Shenandoah Valley Atelier: NEW Waynesboro Loft
Waynesboro
10.0 out of 10, Exceptional, (13 reviews)
"This property is comfortable, restful, and beautiful. Very clean and had everything we needed."
United States
Kathy B.
The price is NZ$438
includes taxes & fees
13 May - 14 May
Shenandoah Valley Atelier: NEW Waynesboro Loft

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (70 reviews)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
The price is NZ$406
includes taxes & fees
17 May - 18 May
Stay in Crozet Train Suite in Downtown Crozet

Renovated Wintergreen Condo with Pool Access, and more!

Renovated Wintergreen Condo with Pool Access, and more!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is NZ$500
includes taxes & fees
20 May - 21 May
Renovated Wintergreen Condo with Pool Access, and more!

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
The price is NZ$625
includes taxes & fees
13 May - 14 May
Serenity Cabin-Woodland Retreat

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (108 reviews)
"Very clean and amazing location. Owners are very communicative. We certainly plan on returning in the future. "
United States
Anthony C.
The price is NZ$560
includes taxes & fees
25 May - 26 May
High Street | Walk to Everything Crozet | Pet-Friendly

Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (31 reviews)
"The location was great and the place was very nice. "
United States
Amanda L.
The price is NZ$246
includes taxes & fees
21 May - 22 May
Unit 5 - Cozy Lower Level Studio Suite

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (25 reviews)
"Clean property, spacious kitchen, accurate description, the laundry in the property added to the convenience. It was pleasant to stay in the property. Just make sure to get in touch with the host the night before check in or few hours before, because they might not respond back right away and the key to the property is a bit tricky."
United States
Caroline
The price is NZ$534
includes taxes & fees
18 May - 19 May
The Cottage @ Afton Mountain- Close to Wineries!

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (60 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is NZ$192
includes taxes & fees
24 May - 25 May
The Firefly Springhouse
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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Top Greenwood Hotel Reviews

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, 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 NZ$147 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?

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!: This holiday home rental outside of Greenwood is located in the city centre, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

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 Charlottesville Ice Park, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. 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.