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Holiday Rentals in Greenwood

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Holiday Rentals in Greenwood

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

9.0 out of 10, Wonderful, (22)
"The house suited us perfectly for our stay. I grew up in the area and know Greenwood pretty well, so felt like home :-) "
The price is €222
includes taxes & fees
14 Jul - 15 Jul
Isolated cottage with good view close to many winery and Brewers.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (189)
"I liked that it's has regular door keys. Loved it!"
The price is €108
includes taxes & fees
13 Jul - 14 Jul
Valley Extended Suites

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

9.0 out of 10, Wonderful, (283)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is €212
includes taxes & fees
13 Jul - 14 Jul
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

10.0 out of 10, Exceptional, (12)
"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."
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

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 €224
includes taxes & fees
14 Jul - 15 Jul
Love Ridge Mountain Lodging

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

9.6 out of 10, Exceptional, (308)
"Exactly as advertised. Clean, everything worked, great location."
The price is €337
includes taxes & fees
16 Jul - 17 Jul
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

9.6 out of 10, Exceptional, (40)
"Property was incredibly clean and well-maintained. Enjoyed this condo!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

10.0 out of 10, Exceptional, (57)
"Wonderful getaway with beautiful outdoor space! "
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (237)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Afton Mountain Vineyards

2.5 star property
The price is €324
includes taxes & fees
13 Jul - 14 Jul
Afton Mountain Vineyards

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

Numerous On-Site Trails: Earlysville Wooded Cabin

10.0 out of 10, Exceptional, (71)
"Wonderful cabin in the woods near Shenandoah NP. It was lovely to hear the birds in the morning. The porch is a wonderful place for coffee. The bed was comfortable. The hosts were friendly and check in was easy. Be sure to plan ahead food wise, there aren’t restaurants or stores nearby. This was a wonderful retreat!"
Numerous On-Site Trails: Earlysville Wooded Cabin

Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

10.0 out of 10, Exceptional, (12)
"The house was lovely. The location was great. Plenty of space for everyone. We really enjoyed this home."
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (227)
"Thanks for sharing your cabin with us! We loved the fireplace and had all the tools we needed for cozy meals."
Rustic Mountain Retreat-Bear Paw

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

9.6 out of 10, Exceptional, (128)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is €218
includes taxes & fees
13 Jul - 14 Jul
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Charming Updated 3 Bedroom Home Near Downtown

9.8 out of 10, Exceptional, (55)
"Super accommodating host and very nice property— clean and comfortable. "
The price is €384
includes taxes & fees
13 Jul - 14 Jul
Charming Updated 3 Bedroom Home Near Downtown

Hike in Shenandoah National Park this June!

9.8 out of 10, Exceptional, (100)
"Charming little house with a big bathroom! Very clean and comfy. "
Hike in Shenandoah National Park this June!

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (78)
"We absolutely loved our stay here! Absolutely beautiful property inside and out, perfect cozy spot, caught the snow which was beautiful! Only 15 minutes from town. We will definitely be back, and we loved the Alley Light suggestion from the owner which was incredible! All around it was a perfect stay, thank you!"
1802 cottage once part of Monticello and owned by Thomas Jefferson

The White Elephant Inn Getaway w/ Pool & Hot Tub!

9.8 out of 10, Exceptional, (70)
"Enjoyed our stay!"
The White Elephant Inn Getaway w/ Pool & Hot Tub!

Secluded cabin on a horse farm, bordered by the North River

10.0 out of 10, Exceptional, (58)
"Great place to stay "
The price is €257
includes taxes & fees
14 Jul - 15 Jul
Secluded cabin on a horse farm, bordered by the North River
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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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.