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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Greenwood vacation rentals

An outdoor patio with stone flooring, string lights, and various plants.

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (93 reviews)
"Really cute place, nicely appointed and comfortable."
United States
Laurie R.
The price is ￥25,873
￥37,789 total
includes taxes & fees
Nov 15 - Nov 16
Guesthouse
A spacious living room with a high ceiling and hardwood trim, a kitchen in the background, and a dining area.

2. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (131 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
The price is ￥26,831
￥41,475 total
includes taxes & fees
Nov 15 - Nov 16
Stay in Crozet Mountain Suite in Downtown Crozet
A forested area with a gravel path leading to a dog park.

3. High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (116 reviews)
"perfect location to montfair resort where we attended wedding...coffee within walking distance, very clean house, kitchen well stocked, had a fantastic time ..highly recommend you visit here for your stay..."
United States
karen r.
The price is ￥35,775
￥56,975 total
includes taxes & fees
Dec 8 - Dec 9
High Street | Walk to Everything Crozet | Pet-Friendly
A wooden cabin with a red door, a welcome sign, a small porch with a chair, and a view of the outside.

4. Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC

Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
Afton
10.0 out of 10, Exceptional, (21 reviews)
"Cute property that was super clean and comfortable! Enjoyed our stay and would definitely visit again!"
United States
Kevin
The price is ￥25,873
￥43,334 total
includes taxes & fees
Nov 16 - Nov 17
Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
Street view

5. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (283 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is ￥18,207
￥20,265 total
includes taxes & fees
Nov 15 - Nov 16
Valley Extended Suites
A wooden deck with a table and chairs, surrounded by lush greenery.

6. Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Charlottesville
9.8 out of 10, Exceptional, (70 reviews)
"What a wonderful retreat! It had everything we needed, was clean and comfortable and afforded us tranquility after working our booth at a local art fair. We look forward to staying there again. We did have a challenge trying to unlock the door upon arrival, but a quick call to the owner took care of that."
United States
Fay
The price is ￥19,964
￥25,011 total
includes taxes & fees
Nov 15 - Nov 16
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
A grassy field with a dining area featuring tables and chairs under green umbrellas, set against a backdrop of hills and a distant building.

7. The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (43 reviews)
"A lovely place to stay and relax! Not far to get to wineries and to Charlottesville. Thank you for a lovely stay!"
United States
Mary R.
The price is ￥23,142
￥48,767 total
includes taxes & fees
Nov 16 - Nov 17
The Cottage @ Afton Mountain- Close to Wineries!
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

8. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (49 reviews)
"Great little cabin"
United States
Travis W.
The price is ￥21,561
￥38,133 total
includes taxes & fees
Nov 22 - Nov 23
Willow Haven: Cozy cabin in delightful Afton
A building facade with a blue door labeled "Stay in Crozet" and a stone wall.

9. Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (74 reviews)
"Great communication and clear details. Awesome spot for the Crozet area. Easy walking to dining options."
United States
Brian
The price is ￥26,831
￥41,475 total
includes taxes & fees
Nov 29 - Nov 30
Stay in Crozet Train Suite in Downtown Crozet
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

10. Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (98 reviews)
"The home was comfortable, quaint, and unique. Everything was in order upon arrival and the stay was overall enjoyable."
United States
Joel F.
The price is ￥28,604
￥51,497 total
includes taxes & fees
Nov 16 - Nov 17
Ivy Rose Cottage nestled b/t Cville & Vineyards
A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

11. Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet
9.8 out of 10, Exceptional, (35 reviews)
"Fantastic stay. Happy to return next time."
United States
Sam B.
The price is ￥21,986
￥68,211 total
includes taxes & fees
Nov 16 - Nov 17
Rosé All Day: Wine Country Getaway! Walk to Dining
A hallway with a wooden floor, a patterned rug, a wooden bench, a chair, a wooden cabinet, and a door with windows.

12. Mountain View Cottage | Wine, Hiking & Dog Friendly

Mountain View Cottage | Wine, Hiking & Dog Friendly
Afton
9.8 out of 10, Exceptional, (57 reviews)
"A beautiful inviting place to stay! Great communication from check in to check out."
United States
Dustin S.
Mountain View Cottage | Wine, Hiking & Dog Friendly
A house with a dark front door, two potted plants on either side, and a sign above the door.

13. Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
9.4 out of 10, Exceptional, (16 reviews)
"Looks brand new and very clean. Nice place."
United States
Ron C.
The price is ￥24,303
￥30,155 total
includes taxes & fees
Nov 16 - Nov 17
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A wooden porch with a bench and railing, surrounded by lush greenery.

14. Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (71 reviews)
"Beautiful place and easy access to wineries and breweries in the area! The cottage was very clean, cozy and accommodating. Will come again!"
United States
Allison H.
The price is ￥23,477
￥43,081 total
includes taxes & fees
Dec 8 - Dec 9
Unique Cypress cottage, close to Charlottesville with mountain views.
A room with a dark grey sofa, a white lamp, and a large abstract painting on the wall.

15. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (17 reviews)
"Our stay was fantastic! Great location for wineries and hiking. Perfect for a couples getaway for privacy and quaintness. Will definitely consider booking again if we ever come back to the area!! "
United States
Liz D.
The price is ￥25,937
￥51,693 total
includes taxes & fees
Nov 18 - Nov 19
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

16. Petite Pink Cottage, Perfect for Solo Travelers

Petite Pink Cottage, Perfect for Solo Travelers
Charlottesville
10.0 out of 10, Exceptional, (10 reviews)
"A very special, unique property. We enjoyed our stay in the cozy, cute, clean cottage. Great location. We will return again."
United States
Tracy
The price is ￥57,305
￥76,412 total
includes taxes & fees
Nov 16 - Nov 17
Petite Pink Cottage, Perfect for Solo Travelers
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

17. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"We and our dog stayed for a weekend at the cottage. The cottage was very clean, nicely decorated and welcoming, the kitchen had all the needed appliances and cookware, only sugar and coffee were provided. The back porch was rather dusty though which made the outdoor area less pleasant to use. Communication with the host was clear and easy. Overall we had a great experience at the cottage and plan on returning."
United States
Mihaela B.
The price is ￥72,582
￥97,821 total
includes taxes & fees
Nov 24 - Nov 25
Charming Cottage Near Vineyards
A covered patio with two patterned chairs, a hanging planter with flowers, and a view of a lush garden.

18. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (59 reviews)
"It was a couple very cozy place for us to stay in the perfect location."
United States
Linda W.
The price is ￥21,086
￥36,164 total
includes taxes & fees
Nov 17 - Nov 18
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A covered porch with hanging plants and a white railing.

19. The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (26 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is ￥19,964
￥30,752 total
includes taxes & fees
Dec 9 - Dec 10
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A house surrounded by dense forest with a clear view of the surrounding landscape.

20. Rockwell Ridge | Inn with Afton Mountain Views

Rockwell Ridge | Inn with Afton Mountain Views
Afton
The price is ￥21,000
￥67,295 total
includes taxes & fees
Nov 30 - Dec 1
Rockwell Ridge | Inn with Afton Mountain Views
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

A courtyard with a brick pathway, surrounded by neatly trimmed hedges and trees, leading to a building with a tiled roof and brick walls.
English Inn of Charlottesville

English Inn of Charlottesville

English Inn of Charlottesville
The Meadows

10/10 Excellent

The decor was of the times if visiting Monticello, etc. with excellent location to historical sites and the service was great. The rooms were clean and the breakfast was top notch!!!...even had french toast with perfectly cooked bacon😍...Will definitely stay there again❣️
United States
Tina
Reviewed June 14, 2025
English Inn of Charlottesville

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Greenwood!

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?

RiverFront Country Home with Blue Mountain Views: This vacation home near Greenwood is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family.

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 Virginia Discovery Museum, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. 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.