Photo by Karyn Leary

Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (158)
"Stayed one night... very clean and comfortable. Not a ton of dishes but kitchen was nice."
The price is AU$165
includes taxes & fees
1 Oct - 2 Oct
Valley Extended Suites
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (253)
"This gorgeous townhouse was perfectly clean and very comfortable for our stay. The view is incredible! It is definitely a mountain getaway, so stock up on essentials before driving up there, but once you are there you won't be disappointed!!"
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Lovely Wooded Cabin with Numerous Trails On-Site!
10.0 out of 10, Exceptional, (55)
"The property was very nice with great walking paths through the woods. A covered porch to sit and watch the wildlife. The hosts were resourceful and accommodating."
Lovely Wooded Cabin with Numerous Trails On-Site!
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, (276)
"Stayed here with some friends on a quick golf trip and it was an ideal spot. The house is well-maintained and having 4 full sized beds worked out great. The host is an excellent communicator and was quick to answer any questions we had. "
The price is AU$597
includes taxes & fees
1 Oct - 2 Oct
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, (223)
"This cabin was perfect for an extended family vacation. The location is remote enough to enjoy some quiet time and enjoy the surroundings, but close enough to venture out for hiking, fishing, and beer/wine tasting. The bedrooms are well situated so we weren't on top of each other. The covered porch and rocking chairs were the best part of the house! "
Restored Double Log Cabin on 400 Mountain Acres
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
10.0 out of 10, Exceptional, (187)
"Fantastic place for a work retreat, more privacy than I've ever experienced at a rental with acres of woods and a gated entrance. It was unusually hot for June, but there was still plenty of space and activities inside during the mid-day heat. Whether you're into fishing, canoeing/kayaking, sunbathing, campfires, board games, foosball/pool, hiking, or swimming, there are activities for everyone. I took the kayak out each morning to fish, ended up catching a bunch of bluegill and a few small...
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
10.0 out of 10, Exceptional, (33)
"Great location at the base of Shenandoah National Park. Clean cabin, well-stocked kitchen. So nice to sit on porch with coffee and listen to the stream and the birds. Thanks for your hospitality!!"
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
View from the Top
10.0 out of 10, Exceptional, (41)
"Incredible view, nicely furnished, everything needed for cooking was in there in the kitchen. Wonderful, and unexpected, wood - burning fireplace made the evenings delightful. ⭐️⭐️⭐️⭐️⭐️"
View from the Top
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (229)
"Great hosts and were very friendly"
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Best views on Mountain! Breathtaking 5 Star. Available August 26-31! BOOK NOW!
10.0 out of 10, Exceptional, (220)
"This unit was perfect for a weekend getaway with my husband and friends. We thoroughly enjoyed the gorgeous views and the unit size was great for the 4 of us! We'll definitely consider staying here again when we come back this way!"
Best views on Mountain! Breathtaking 5 Star. Available August 26-31! BOOK NOW!
Rustic Mountain Retreat-Bear Paw
9.8 out of 10, Exceptional, (212)
"We enjoyed our stay. We didn't have neighbors although there are cabins on either side so we were alone which was nice."
Rustic Mountain Retreat-Bear Paw
Ivy Rose Cottage nestled b/t Cville & Vineyards
10.0 out of 10, Exceptional, (23)
"A lovely property to stay in"
The price is AU$542
includes taxes & fees
7 Oct - 8 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
9.8 out of 10, Exceptional, (72)
"Pictures are accurate. Beautiful view from huge windows. This unit is on the top floor so be ready for some stairs. Great location, easy uber ride to mall and easy ride to UVA. "
The price is AU$412
includes taxes & fees
20 Oct - 21 Oct
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
10.0 out of 10, Exceptional, (59)
"Sent a couple here for their honeymoon and they had an amazing time! "
The price is AU$289
includes taxes & fees
1 Oct - 2 Oct
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Cozy cabin for 2 w/ great mt views & walking trails!
10.0 out of 10, Exceptional, (136)
"What a wonderful property...view was amazing, property was clean, well appointed, and the perfect backdrop for a memorable stay. Particularly liked the propane firepit and back porch experience, highlight of the property!! Everything you needed (plus some!) and nothing you don't. Will definitely be booking again."
The price is AU$280
includes taxes & fees
22 Oct - 23 Oct
Cozy cabin for 2 w/ great mt views & walking trails!
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, (61)
"I recently stayed here with my husband and our six kids. The house is beautiful, clean, and very cozy! The driveway is a bit intimidating but we got used to it fairly quickly. Overall it was a nice place and we would definitely stay here again."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (288)
"Enjoyed our stay. Property wa"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
The newest and largest edition to the Wintergreen Retreat portfolio!
9.6 out of 10, Exceptional, (34)
"We couldn’t have had a better weekend! Our host was very easy to communicate with and the house was beautiful. Would highly recommend for large gatherings. Proximity to outlooks and outdoor activities can’t be beat!"
The newest and largest edition to the Wintergreen Retreat portfolio!
Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (45)
"Very clean, everything we needed was provided"
The price is AU$471
includes taxes & fees
1 Oct - 2 Oct
Endless Mountain Top Views from All The Way Up!
1802 cottage once part of Monticello and owned by Thomas Jefferson
9.4 out of 10, Exceptional, (66)
"This is a hidden gem in a convenient location near a winery and historical attractions. Definitely for a nature lover! No frills or fuss-just a cool place with nice amenities. The Jefferson dwelling is not for tall people as the ceiling is low. The host is hospitable and the place is very clean."
1802 cottage once part of Monticello and owned by Thomas Jefferson
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Other types of properties in Greenwood you may be interested in

English Inn of Charlottesville
3.0 star property
9.0 out of 10, Wonderful, (1834)
"Extremely clean room."
The price is AU$177
includes taxes & fees
1 Oct - 2 Oct
English Inn of Charlottesville
Sleep Inn Staunton
2.5 star property
9.2 out of 10, Wonderful, (1013)
"Cleanliness, politeness, Great breakfast "
The price is AU$138
includes taxes & fees
14 Oct - 15 Oct
Sleep Inn Staunton
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
3.0 star property
9.0 out of 10, Wonderful, (1007)
"Nice breakfast "
The price is AU$170
includes taxes & fees
15 Oct - 16 Oct
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.

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 Veritas Vineyard and Winery.

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.