Vacation rentals in Greenwood

Stylish Carriage House Suite near Crozet center

Peaceful retreat walkable to downtown Crozet (cafes, galleries, restaurants, yoga, spa.) One bedrm, now with Queen, clawfoot tub, stovetop, granite countertops, reclaimed barn wood features, visual electric "fireplace" focal point, and private deck. (Access to main house yard w permission each time.) One small non-shed dog on Nexgard with permission and fee. (Some other breeds with discussion and sweep on check-out.) We give winery tours thru CrozetTrolley. Main house next door for large groups

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 bedroom suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

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.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy 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.

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.

Best Spot on the Wine/Brew Trail!

Charming, private, efficiency apartment located in the center of winery/brewery country! This efficiency offers fiber internet (super fast)! Less than a minute to Blue Mountain Brewery, Flying Fox Vineyard, and Valley Road Vineyard. Less than 5 minutes to Veritas Vineyard, Cardinal Point Vineyard, Silver Back Distillery, Afton Mountain Vineyards. 5-10 minutes to Bold Rock Cidery, Devils Backbone Brewery, Brewing Tree Brewery, Mountain Meadery, Hill Top Berry Farm, and so many more.

Mountain View Getaway Yurt

Come enjoy country living in beautiful western Albemarle county. Our yurt is on a 13 acre property on a quiet country road. (My husband and I also have our home about 200 ft away from yurt). The yurt features a relaxing outdoor claw foot tub/shower with beautiful country views. The private bathroom is situated on the deck of the yurt. The pool is a shared space directly behind our home. The wooded part of the property is private with a beautiful walking trail for you to enjoy.

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

The Barn at Haden near Wineries and C'ville

The Barn at Haden is a custom well appointed finished 2 bedroom, 1 full bath space elevated above a detached 3 car garage with a large outdoor private deck. It features a fully equipped gourmet kitchen with high end finishes. Whether staying for a night or for the weekend, it is an experience to enjoy the easy living Crozet has to offer. Walkable/bikeable to downtown Crozet, 2 miles to King Family Vineyard & Chiles Peach Orchard and 15 minutes from Charlottesville.

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a little farmette. 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

Wintergreen Escape | King Bed + Porch Views

Escape to our four-season Wintergreen condo! Enjoy crisp mountain air, scenic hikes, fall foliage, and nearby wineries and breweries. Walk to Discovery Ridge, the spa, and activities! Relax at the seasonal heated pool, play a round of golf, or explore the Blue Ridge Parkway and Shenandoah National Park. Perfect for couples or families, cook a cozy meal or unwind by the fire after a day outdoors!

Walker's dream. Close to downtown.

Centrally located near the library, Gypsy Hill Park, and downtown Staunton, our private, walkout basement apartment has individually controlled heating and air conditioning. It includes a brick patio, private rear entrance and historic details from the late 1800's. It is generally quiet, but you may sometimes hear the two adults upstairs. Come enjoy this peaceful and centrally-located space.