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Greenwood Vacation Rentals

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Vacation Rentals in Greenwood

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 CA $248
CA $361 total
includes taxes & fees
Aug 4 - Aug 5
Isolated cottage with good view close to many winery and Brewers.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (190)
"Quite and Accommodating.office staff was great "
The price is CA $138
CA $154 total
includes taxes & fees
Aug 13 - Aug 14
Valley Extended Suites

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

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."
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

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

9.0 out of 10, Wonderful, (288)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is CA $145
CA $336 total
includes taxes & fees
Aug 5 - Aug 6
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Stylish Belmont Studio: Walk to Downtown Mall

9.6 out of 10, Exceptional, (92)
"Beautiful place and great location. We will be back!"
Stylish Belmont Studio: Walk to Downtown Mall

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (57)
"The cottage was super adorable and perfect for our little weekend getaway!!! "
The price is CA $248
CA $468 total
includes taxes & fees
Aug 11 - Aug 12
Ivy Rose Cottage nestled b/t Cville & Vineyards

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

9.8 out of 10, Exceptional, (47)
"This was a perfect spot for exploring Charlottesville for a few days. Loved being so close to the downtown mall, an easy walk to explore shops and restaurants there, and also the great restaurants in the Belmont neighborhood. "
The price is CA $210
CA $364 total
includes taxes & fees
Aug 10 - Aug 11
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

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

10.0 out of 10, Exceptional, (238)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

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

9.4 out of 10, Exceptional, (69)
"Second stay here and all good!! "
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

10.0 out of 10, Exceptional, (45)
"Well designed modern cabin on the Rockfish River south of CVille. Plenty of space to amble around with a small beach where you could launch kayaks (provided) or do some fishing.Had great time even though it was a little rainy."
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

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 CA $248
CA $361 total
includes taxes & fees
Aug 4 - Aug 5
Love Ridge Mountain Lodging

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

10.0 out of 10, Exceptional, (321)
"I’ve stayed here a few times now with various members of my family and all of us love this place! The accommodations are great, the place is well stocked with careful attention to detail, and we always look forward to returning. Thanks again for a great stay!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

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

10.0 out of 10, Exceptional, (60)
"Great place to stay "
The price is CA $186
CA $403 total
includes taxes & fees
Aug 3 - Aug 4
Secluded cabin on a horse farm, bordered by the North River

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (81)
"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

Charming Updated 3 Bedroom Home Near Downtown

9.8 out of 10, Exceptional, (57)
"Very clean, nicely updated rental. The beds were comfortable and the family room/kitchen in the r back of the house is a great place to relax and play games. The owners were very helpful and communicative. "
The price is CA $279
CA $607 total
includes taxes & fees
Aug 7 - Aug 8
Charming Updated 3 Bedroom Home Near Downtown

Numerous On-Site Trails: Earlysville Wooded Cabin

10.0 out of 10, Exceptional, (71)
"We absolutely loved how beautiful this little cabin is. Loved sitting on the front porch drinking my coffee in the mornings and listening to the birds chirp. This place is so peaceful and relaxing. Barbara was a wonderful host and came over to check to see if we needed anything. Great location to visit all the local towns around the area and only 30 minutes from the Byrd visitor center and Shenandoah national Park. We would definitely stay here again."
Numerous On-Site Trails: Earlysville Wooded Cabin

You'll say "Wow!" Over This 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."
You'll say "Wow!" Over This View!

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

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

9.6 out of 10, Exceptional, (130)
"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 CA $152
CA $341 total
includes taxes & fees
Aug 5 - Aug 6
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
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

Frequently asked questions

Can I find vacation rentals in Greenwood?

Yes, there are vacation rentals close to top sights in Greenwood, or you can select a more remote option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best vacation rentals that Greenwood has to offer?

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!: This vacation home rental near Greenwood is located in the city center 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 a coffee maker.

How many vacation rentals will I find in Greenwood?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a vacation rental in Greenwood like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Greenwood. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.