Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

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Guest favorite

Cottage in Crozet

4.89 out of 5 average rating, 204 reviews

The Carriage House

Spacious 2 bedroom Carriage House in Crozet. Each of 2 bedrooms has a queen bed with a queen sleeper sofa in living room. Enjoy a quiet country setting with convenience to hiking, outdoor activities, wineries & breweries. Relax & unwind on the screened porch, enjoy meals in the full kitchen and convenience of in unit laundry. The Carriage house is the perfect place for a weekend trip or an extended stay in Central Virginia. You'll have the house to yourself with the ease of keypad self check-in.

Sep 24 – Oct 1

G$26,204 GYD per night

Guest favorite

Cottage in Afton

4.97 out of 5 average rating, 182 reviews

Private Forest Cottage near Pippin Hill/Wineries

Completely renovated in 2019, our private forest cabin in the heart of the Blue Ridge mtns and Albemarle wine/brewery country is perfect for getaways, weddings and outdoor enthusiasts. A picturesque oasis with an eco-friendly design (Separett composting toilet!), the cabin has a loft with queen bed and sleeper sofa in living area, 3 porches, private parking, neighborhood swimming pond, hiking trails right out your door, Crozet 10 mins, Wintergreen 30 mins; Cville 20 mins, Shenandoah 15 mins.

Aug 8 – 15

G$24,576 GYD per night

Guest favorite

Cottage in Waynesboro

4.92 out of 5 average rating, 198 reviews

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! Walk to Historic Waynesboro (<1 mile) and the riverside park, or its restaurants and stores to entertain even the peculiar palate or collector. Fully fenced in back yard, so bring the pups or the kids, but watch for wildlife! Hiking store nearby.

Jan 16 – 23

G$23,105 GYD per night

Guest favorite

Apartment in Afton

4.99 out of 5 average rating, 134 reviews

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

Jul 4 – 11

G$31,162 GYD per night

Guest favorite

Home in Greenwood

5.0 out of 5 average rating, 152 reviews

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and plenty of games.

Apr 1 – 8

G$115,733 GYD per night

Guest favorite

Cottage in Afton

4.99 out of 5 average rating, 158 reviews

Oasis in the Blue Ridge -Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

Aug 16 – 23

G$33,590 GYD per night

Guest favorite

Cabin in Afton

4.94 out of 5 average rating, 409 reviews

Wes Cabin - Great space for a getaway from home!

This cabin sits on a 5 acre lot close to I.64 and Rt.250. It has nice mountain views from private back deck. It is close to (5 mins) the Blue Ridge Parkway and Skyline Drive. Also a short drive to all the local wineries and breweries. A Great location for hikers and cyclists! The Cabin is cozy/rustic with character. It has everything you should need to make your stay comfortable. Due to the coronavirus, we clean, sanitize and disinfect frequently touched hard surfaces between reservations.

Feb 3 – 10

G$27,340 GYD per night

Guest favorite

Guesthouse in Crozet

4.98 out of 5 average rating, 118 reviews

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

Jul 15 – 22

G$21,757 GYD per night

Guest favorite

Guest suite in Waynesboro

4.98 out of 5 average rating, 195 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Modern amenities, complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is all yours including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Nov 26 – Dec 3

G$22,093 GYD per night

Guest favorite

Cabin in Rockbridge Baths

4.97 out of 5 average rating, 268 reviews

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

Oct 11 – 18

G$23,191 GYD per night

Guest favorite

Guest suite in Crozet

4.97 out of 5 average rating, 147 reviews

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a mini working farm. This peaceful setting tucked away on several acres along a creek with nature trails is the perfect mountain getaway. We are conveniently situated near quaint wineries, breweries along with hiking and the Blue Ridge Parkway that is a short hop, jump and a skip away. Every effort has been made to keep this a green haven, chemical and synthetic scent free, so you can leave recharged and rested. Non-smoking

Nov 30 – Dec 7

G$24,772 GYD per night

Guest favorite

Guesthouse in Afton

5.0 out of 5 average rating, 114 reviews

WEEKENDS, WINE & WAHOOS! - Private Detached Studio

Enjoy an escape in the heart of Virginia wine country! This renovated, detached studio is only 22 mins. south of Charlottesville & UVa. Whether you're attending a wedding or exploring everything the area has to offer, it's an ideal spot. You're close to multiple vineyards, Shenandoah NP/The Blue Ridge Parkway, breweries & hiking. Plus, there's fast, reliable internet & your own deck for relaxing.

May 31 – Jun 5

G$23,724 GYD per night