Photo by Karyn Leary

Holiday Rentals in Greenwood

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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 €229
includes taxes & fees
1 Sept - 2 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, (193)
"Quite and Accommodating.office staff was great "
The price is €109
includes taxes & fees
31 Aug - 1 Sept
Valley Extended Suites

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

10.0 out of 10, Exceptional, (14)
"We loved staying at this property. Easily accommodated our family and was such a pretty setting. Host was excellent in answering questions and providing information. Would definitely stay here in the future."
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (86)
"This is a great place to stay. Close to town but out on a large very private farm. Highly recommend. "
1802 cottage once part of Monticello and owned by Thomas Jefferson

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

9.0 out of 10, Wonderful, (291)
"We stayed at the condo in end of May. Beautiful view, nice location in hills. "
The price is €209
includes taxes & fees
14 Sept - 15 Sept
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Afton Mountain Vineyards

2.5 star property
The price is €337
includes taxes & fees
1 Sept - 2 Sept
Afton Mountain Vineyards

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

9.6 out of 10, Exceptional, (133)
"This was such a beautiful, clean space. Every item had been thought of; there was even a closet with dog treats, flashlights, extra toothbrushes, etc! Parking and check in were a breeze. The host was incredibly responsive. Take the short walk to Fire and Frost for delicious pizza!"
The price is €220
includes taxes & fees
1 Sept - 2 Sept
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

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

Family Friendly Log Cabin Nestled in Blue Ridge Foothills

2.0 star property
9.8 out of 10, Exceptional, (10)
"Very well equipped and clean! The owner was super nice and responsive! Great stay!"
Family Friendly Log Cabin Nestled in Blue Ridge Foothills

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

9.4 out of 10, Exceptional, (75)
"Second stay here and all good!! "
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

Wow! What A View!

9.4 out of 10, Exceptional, (15)
"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!

Cozy Cabin with private HOT TUB!

10.0 out of 10, Exceptional, (25)
"Adult girls weekend visiting local wineries, Breweries, and, of course, Bold Rock Cidery. Great location. Beautiful mountain views on the way up to the cabin. The hot tub was perfect for evening relaxation. Plenty of room, and well-appointed kitchen. "
Cozy Cabin with private HOT TUB!

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (37)
"The Ivy Rose Cottage was very comfortable and creatively decorated. The kitchen is nicely supplied for cooking simple meals. The trains did not disturb us and were fun to watch, especially the Amtrak. Great pizza and local brewery in nearby Crozet plus an excellent Harris Teeter grocery. Highly recommend this location for anyone looking for an out-of-town stay. "
The price is €264
includes taxes & fees
2 Sept - 3 Sept
Unique Cypress cottage, close to Charlottesville with mountain views.

Bear Tracks Cottage: New Hot Tub + Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (20)
"Great for taking advantage of all Nelson County's attractions. "
The price is €379
includes taxes & fees
1 Sept - 2 Sept
Bear Tracks Cottage: New Hot Tub + Fire Pit

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (27)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
The price is €249
includes taxes & fees
8 Sept - 9 Sept
Panoramic Peak: Wintergreen Condo with Views

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (59)
"The cottage was super adorable and perfect for our little weekend getaway!!! "
The price is €297
includes taxes & fees
1 Sept - 2 Sept
Ivy Rose Cottage nestled b/t Cville & Vineyards

Aftonshire Cottage - Heart of Afton's Wine Region

10.0 out of 10, Exceptional, (4)
"Place was nice an quite and had a good view of the horses outback. The location was great and close to restaurants and wineries. "
Aftonshire Cottage - Heart of Afton's Wine Region

The Firefly Springhouse

10.0 out of 10, Exceptional, (32)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is €102
includes taxes & fees
1 Sept - 2 Sept
The Firefly Springhouse

Old Met #306 | 1 Bedroom, 2 Bath

9.6 out of 10, Exceptional, (62)
"Great spot and roomy apartment!"
The price is €216
includes taxes & fees
2 Sept - 3 Sept
Old Met #306 | 1 Bedroom, 2 Bath

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

9.8 out of 10, Exceptional, (48)
"Great place to stay in Wintergreen!"
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 €102 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 a Smart TV 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 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.