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Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Our top choices for Greenwood holiday rentals

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is NZ$442
includes taxes & fees
8 Sept - 9 Sept
Isolated cottage with good view close to many winery and Brewers.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (196)
"Nice stay"
The price is NZ$179
includes taxes & fees
10 Sept - 11 Sept
Valley Extended Suites

Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

Wow! What A View!

9.4 out of 10, Exceptional, (16)
"Découverte de la corse pour la 1ère fois. Proche de tous, plage, équitation mer montagne, spécialités, petit port avec restau,rando, village et super point de vue."
Wow! What A View!

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (240)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (59)
"Loved staying here!"
The price is NZ$574
includes taxes & fees
8 Sept - 9 Sept
Ivy Rose Cottage nestled b/t Cville & Vineyards

Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

9.8 out of 10, Exceptional, (158)
"My sister and I hubbed out of Charlottesville for three days as we traveled around Western VA visiting family. The cottage is quiet, in a safe little neighborhood a block from West Main St, where we found lots of great dining and shopping options. It was a perfect little base from which to explore the nearby mountains and countryside. "
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

Aftonshire Cottage - Heart of Afton's Wine Region

9.8 out of 10, Exceptional, (6)
Aftonshire Cottage - Heart of Afton's Wine Region

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is NZ$474
includes taxes & fees
10 Sept - 11 Sept
Love Ridge Mountain Lodging

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (47)
"We took our two kids and our poodle, Rocky, for a few days of hiking and unplugging! It was the perfect spot!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Downtown Carriage House | 1 BR Loft close to the historic downtown mall

9.4 out of 10, Exceptional, (76)
"Great Quite getaway near down town"
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (28)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
The price is NZ$499
includes taxes & fees
9 Sept - 10 Sept
Panoramic Peak: Wintergreen Condo with Views

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (39)
"Perfect location for winery, golf, dining and shopping in the Crozet and Charlottesville area. I would definitely recommend and consider staying here again."
The price is NZ$481
includes taxes & fees
8 Sept - 9 Sept
Unique Cypress cottage, close to Charlottesville with mountain views.

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (229)
"Can’t wait to go back"
Rustic Mountain Retreat-Bear Paw

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (60)
"Great location, amenities and owner's willingness to address all our questions/issues."
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Cottage at Deer Ridge Farm

10.0 out of 10, Exceptional, (1)
"as advertised"
Cottage at Deer Ridge Farm

Cozy 6-bedroom cabin in Wintergreen Resort

9.8 out of 10, Exceptional, (9)
"Place was great we had a blast ! Only about a 5 min walk to the slopes!"
Cozy 6-bedroom cabin in Wintergreen Resort

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

10.0 out of 10, Exceptional, (325)
"Great location to check out all that the Wintergreen area has to offer. The condo was cozy and well stocked for our long weekend adventure with our son and pup. We are regulars to the area and this was one of our favorite rentals. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (52)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (88)
"Historic property just minutes from Monticello (sightseeing) and the Clifton Inn (dinner). While a bit small, it is a very cozy and appealing place. And very quiet. Having your own hot tub and hammock, and practically your own salt pool, is very special."
1802 cottage once part of Monticello and owned by Thomas Jefferson
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

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$179 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?

Aftonshire Cottage - Heart of Afton's Wine Region: This holiday home rental outside of Greenwood is located in a rural location, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.