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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 NZ$331
includes taxes & fees
5 Oct - 6 Oct
Guesthouse
A deck with wooden chairs and tables, overlooking a grassy field and distant mountains.

2. Cottage on Working Turkey and Bee Farm in the Heart of Crozet

Cottage on Working Turkey and Bee Farm in the Heart of Crozet
Crozet
10.0 out of 10, Exceptional, (45 reviews)
"Lovely little space on a great working farm. Cozy, quiet, and proximity to plenty of amazing nature and activities. Highly recommended "
United States
Thomas G.
The price is NZ$910
includes taxes & fees
30 Oct - 31 Oct
Cottage on Working Turkey and Bee Farm in the Heart of Crozet
A wooden cabin interior with a kitchen, a dining area, and a living room.

3. 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 NZ$542
includes taxes & fees
3 Nov - 4 Nov
Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
A cafe interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

4. 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 NZ$589
includes taxes & fees
7 Oct - 8 Oct
High Street | Walk to Everything Crozet | Pet-Friendly
An outdoor seating area with wooden chairs and a central fire pit, surrounded by a stone wall and a building with a red roof.

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

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (37 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 NZ$567
includes taxes & fees
4 Oct - 5 Oct
The Cottage @ Afton Mountain- Close to Wineries!
Street view

6. 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 NZ$206
includes taxes & fees
13 Oct - 14 Oct
Valley Extended Suites
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

7. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (129 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
The price is NZ$433
includes taxes & fees
5 Oct - 6 Oct
Stay in Crozet Mountain Suite in Downtown Crozet
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

8. 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 NZ$429
includes taxes & fees
4 Oct - 5 Oct
Stay in Crozet Train 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.

9. 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 NZ$579
includes taxes & fees
5 Oct - 6 Oct
Rosé All Day: Wine Country Getaway! Walk to Dining
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

10. 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 NZ$402
includes taxes & fees
5 Oct - 6 Oct
Willow Haven: Cozy cabin in delightful Afton
A hallway with a wooden floor, a patterned rug, a wooden bench, a chair, a wooden cabinet, and a door with windows.

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

Mountain View Cottage | Wine, Hiking & Dog Friendly
Afton
9.8 out of 10, Exceptional, (56 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 rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

12. 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 NZ$605
includes taxes & fees
3 Nov - 4 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

13. 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 NZ$674
includes taxes & fees
3 Nov - 4 Nov
Ivy Rose Cottage nestled b/t Cville & Vineyards
A gravel path leading through a forested area with a sign that reads "LaVoy".

14. 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 NZ$295
includes taxes & fees
6 Oct - 7 Oct
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
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 NZ$614
includes taxes & fees
3 Nov - 4 Nov
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A spacious kitchen with a large island, dark cabinetry, and a stone pendant light.

16. Mountain Mama- Amazing Views! + Hot Tub!

Mountain Mama- Amazing Views! + Hot Tub!
Afton
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful house with beautiful views. "
United States
Jayson K.
Mountain Mama- Amazing Views! + Hot Tub!
A kitchen with white cabinets, a stainless steel sink, a window with a view of greenery, and a countertop with a dish rack and kitchen utensils.

17. Afton escape centrally located on the brew trail

Afton escape centrally located on the brew trail
Afton
10.0 out of 10, Exceptional, (44 reviews)
"We had a wonderful stay at this immaculate, well decorated, fully stocked home! The home is located so close to everything. The couch was SUPER comfy and so were the beds. Would love to stay again if back in the area."
United States
Robyn A.
Afton escape centrally located on the brew trail
A wooden staircase leading to a covered area with a wooden railing and a hanging light fixture.

18. King Deluxe Suite on Afton Mtn | Pet-Friendly!

King Deluxe Suite on Afton Mtn | Pet-Friendly!
Waynesboro
The price is NZ$330
includes taxes & fees
4 Oct - 5 Oct
King Deluxe Suite on Afton Mtn | Pet-Friendly!
A cozy living room with wooden paneling, a fireplace, a grey sofa, and a round coffee table.

19. Afton Farmhouse - Mountain Views off Route 151

Afton Farmhouse - Mountain Views off Route 151
Afton
9.8 out of 10, Exceptional, (29 reviews)
"Conveniently ;located and very easy to access. Very comfortable house and relaxing atmosphere."
United States
Traci S.
The price is NZ$895
includes taxes & fees
3 Nov - 4 Nov
Afton Farmhouse - Mountain Views off Route 151
A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

20. 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 NZ$387
includes taxes & fees
26 Oct - 27 Oct
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Very nice place. Quiet and clean with a modest, simple elegance."
Peter 1-night trip
Posted 5 hours ago
English Inn of Charlottesville

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as NZ$206 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.