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Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (92 reviews)
"Great stay! Perfect location, booked for quick overnight girls trip."
United States
Melissa G.
The price is HK$883
HK$1,457 total
includes taxes & fees
4 Oct - 5 Oct
Guesthouse
Street view

2. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (260 reviews)
"Would stay again 👍"
United States
Jessica
The price is HK$894
HK$996 total
includes taxes & fees
6 Oct - 7 Oct
Valley Extended Suites
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

3. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (39 reviews)
"Great little cabin"
United States
Travis W.
The price is HK$946
HK$1,776 total
includes taxes & fees
5 Oct - 6 Oct
Willow Haven: Cozy cabin in delightful Afton
A wooden deck with a table and chairs, surrounded by lush greenery.

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

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Charlottesville
10.0 out of 10, Exceptional, (64 reviews)
"Great setting and very clean and comfortable."
United States
Jeanie F.
The price is HK$981
HK$1,300 total
includes taxes & fees
6 Oct - 7 Oct
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
A cozy cabin interior with wooden walls, a TV on a wooden stand, a sofa, and a staircase.

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

Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
Afton
9.8 out of 10, Exceptional, (15 reviews)
"Extremely responsive and thoughtful, offered a few suggestions to make it a bit cozier and got a thank you which was great. Would stay again"
United States
Christian G.
The price is HK$1,264
HK$2,213 total
includes taxes & fees
5 Oct - 6 Oct
Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
An outdoor seating area with wooden chairs and a central fire pit, surrounded by a stone wall and a building with a red roof.

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

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (36 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$2,502 total
includes taxes & fees
4 Oct - 5 Oct
The Cottage @ Afton Mountain- Close to Wineries!
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

7. Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (73 reviews)
"Great place to stay!!!"
United States
Brian
The price is HK$1,177
HK$1,926 total
includes taxes & fees
4 Oct - 5 Oct
Stay in Crozet Train Suite in Downtown Crozet
A hotel room with a bed, a nightstand with a lamp, a blue tissue box, and a window with a curtain.

8. Rockwell Ridge | Inn with Afton Mountain Views

Rockwell Ridge | Inn with Afton Mountain Views
Afton
The price is HK$791
HK$3,344 total
includes taxes & fees
25 Oct - 26 Oct
Rockwell Ridge | Inn with Afton Mountain Views
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

9. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (128 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
The price is HK$1,177
HK$1,908 total
includes taxes & fees
5 Oct - 6 Oct
Stay in Crozet Mountain Suite in Downtown Crozet
A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

10. 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, (33 reviews)
"Fantastic stay. Happy to return next time."
United States
Sam B.
The price is HK$1,033
HK$2,598 total
includes taxes & fees
5 Oct - 6 Oct
Rosé All Day: Wine Country Getaway! Walk to Dining
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

11. 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, (25 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is HK$883
HK$1,463 total
includes taxes & fees
4 Oct - 5 Oct
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A dining area with a wooden table and chairs, a chandelier, and a view of the outdoors through a window.

12. Rockwell Ridge | Private Retreat w/ Mountain Views

Rockwell Ridge | Private Retreat w/ Mountain Views
Afton
The price is HK$2,051
HK$6,966 total
includes taxes & fees
13 Oct - 14 Oct
Rockwell Ridge | Private Retreat w/ Mountain Views
A cafe interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

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

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (115 reviews)
"This cute home was perfect for our stay in Crozet! It was close to lovely coffee shops. The home was very clean and communication with the host was fantastic! We would stay here again if in the area."
United States
Jody L.
The price is HK$1,569
HK$2,640 total
includes taxes & fees
4 Oct - 5 Oct
High Street | Walk to Everything Crozet | Pet-Friendly
A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

14. NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (62 reviews)
"The hot tub was excellent! Such a cute, cozy, and accommodating weekend!"
United States
Sally A.
The price is HK$918
HK$1,607 total
includes taxes & fees
4 Oct - 5 Oct
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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$1,229
HK$2,656 total
includes taxes & fees
4 Oct - 5 Oct
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

16. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (21 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is HK$513
HK$1,323 total
includes taxes & fees
6 Oct - 7 Oct
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

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

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (95 reviews)
"Felt like I was in a fairy cottage"
United States
Dionne
The price is HK$1,405
HK$2,647 total
includes taxes & fees
13 Oct - 14 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards
A circular fire pit with a metal rim and a flat top, surrounded by a stone border.

18. Rockwell Ridge | Chestnut Suite with Lux Bathroom

Rockwell Ridge | Chestnut Suite with Lux Bathroom
Afton
The price is HK$1,035
HK$2,212 total
includes taxes & fees
13 Oct - 14 Oct
Rockwell Ridge | Chestnut Suite with Lux Bathroom
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

19. 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, (66 reviews)
"Lovely, charming home."
United States
Deborah R.
The price is HK$1,530
HK$2,708 total
includes taxes & fees
13 Oct - 14 Oct
Unique Cypress cottage, close to Charlottesville with 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

Hotel 24 South

Hotel 24 South

10/10 Excellent
"very open and beautiful lobby. Room and bath clean and comfortable"
susan 1-night trip
Posted 4 hours ago
Hotel 24 South

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 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.