Lodging Image

Greenwood Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Greenwood holiday 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 HK$1,271
HK$1,856 total
includes taxes & fees
18 Nov - 19 Nov
Guesthouse
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

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 HK$1,318
HK$2,037 total
includes taxes & fees
16 Nov - 17 Nov
Stay in Crozet Mountain Suite in Downtown Crozet
A cafe interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

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 HK$1,757
HK$2,799 total
includes taxes & fees
16 Nov - 17 Nov
High Street | Walk to Everything Crozet | Pet-Friendly
A cozy cabin interior with wooden walls, a TV on a wooden stand, a sofa, and a staircase.

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 HK$1,271
HK$2,129 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$894
HK$995 total
includes taxes & fees
16 Nov - 17 Nov
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, (71 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 HK$981
HK$1,229 total
includes taxes & fees
17 Nov - 18 Nov
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
An outdoor seating area with wooden chairs and a central fire pit, surrounded by a stone wall and a building with a red roof.

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 HK$1,137
HK$2,396 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$1,059
HK$1,873 total
includes taxes & fees
20 Nov - 21 Nov
Willow Haven: Cozy cabin in delightful Afton
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

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
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 HK$1,405
HK$2,530 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$1,080
HK$3,351 total
includes taxes & fees
16 Nov - 17 Nov
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 two-story house with a porch, a front door, and a mailbox.

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 HK$1,208
HK$1,498 total
includes taxes & fees
16 Nov - 17 Nov
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

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 HK$1,153
HK$2,116 total
includes taxes & fees
3 Dec - 4 Dec
Unique Cypress cottage, close to Charlottesville with mountain views.
A hot tub on a wooden deck with a wooden railing and a table with chairs.

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 HK$1,274
HK$2,539 total
includes taxes & fees
18 Nov - 19 Nov
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 HK$2,745
HK$3,653 total
includes taxes & fees
16 Nov - 17 Nov
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 HK$3,566
HK$4,805 total
includes taxes & fees
24 Nov - 25 Nov
Charming Cottage Near Vineyards
A compact kitchen with white cabinetry, a blue door, and a white refrigerator.

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 HK$1,035
HK$1,775 total
includes taxes & fees
17 Nov - 18 Nov
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

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 HK$883
HK$1,393 total
includes taxes & fees
16 Nov - 17 Nov
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A spacious living area with a wooden ceiling, a sofa, a coffee table, and a kitchen in the background.

20. Rockwell Ridge | Inn with Afton Mountain Views

Rockwell Ridge | Inn with Afton Mountain Views
Afton
The price is HK$1,201
HK$3,575 total
includes taxes & fees
15 Dec - 16 Dec
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenwood Hotel Reviews

Days Inn by Wyndham Charlottesville/University Area

Days Inn by Wyndham Charlottesville/University Area

8/10 Good
"This hotel is perfectly optimal for a couple of nights. Don’t let the price cause you to think it isn’t nice. The price is perfect and its location to the University couldn’t be any better!"
Franklyn 2-night trip
Posted 12 hours ago
Days Inn by Wyndham Charlottesville/University Area

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:

  • View our selection of featured holiday rentals in Greenwood
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

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

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?

RiverFront Country Home with Blue Mountain Views: This holiday home rental outside of Greenwood is located on a river, and has a patio, a garden 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.

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