Lodging Image

Greenwood Vacation 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Greenwood vacation rentals

Terrace/patio

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (91 reviews)
"Great stay! Perfect location, booked for quick overnight girls trip."
United States
Melissa G.
The price is AED 413
AED 682 total
includes taxes & fees
27 Sep - 28 Sep
Guesthouse
Standard Suite, 1 Queen Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

2. Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.0 out of 10, Wonderful, (70 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is AED 437
AED 486 total
includes taxes & fees
8 Oct - 9 Oct
Affordable Suites of America Waynesboro
Exterior detail

3. 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, (24 reviews)
"Owner was communicative. Lots of space. Decor was unique."
United States
Clement
The price is AED 413
AED 685 total
includes taxes & fees
27 Sep - 28 Sep
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Exterior detail

4. 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 AED 440
AED 828 total
includes taxes & fees
29 Sep - 30 Sep
Willow Haven: Cozy cabin in delightful Afton
Property grounds

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

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (36 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is AED 532
AED 1,163 total
includes taxes & fees
27 Sep - 28 Sep
The Cottage @ Afton Mountain- Close to Wineries!
Exterior detail

6. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (127 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
The price is AED 551
AED 893 total
includes taxes & fees
27 Sep - 28 Sep
Stay in Crozet Mountain Suite in Downtown Crozet
Street view

7. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (258 reviews)
"Would stay again 👍"
United States
Jessica
The price is AED 389
AED 433 total
includes taxes & fees
7 Oct - 8 Oct
Valley Extended Suites
Exterior detail

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)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
The price is AED 551
AED 893 total
includes taxes & fees
27 Sep - 28 Sep
Stay in Crozet Train Suite in Downtown Crozet
Property grounds

9. Rockwell Ridge | Chestnut Suite with Lux Bathroom

Rockwell Ridge | Chestnut Suite with Lux Bathroom
Afton
The price is AED 327
AED 826 total
includes taxes & fees
27 Sep - 28 Sep
Rockwell Ridge | Chestnut Suite with Lux Bathroom
Outdoor dining

10. 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 AED 459
AED 609 total
includes taxes & fees
29 Sep - 30 Sep
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Outdoor spa tub

11. 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)
"Place was exactly as described. We were only passing through for one night but was exactly what we needed. Fenced in backyard for the dog with lots of space."
United States
Brian T.
The price is AED 430
AED 752 total
includes taxes & fees
4 Oct - 5 Oct
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Interior

12. 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 AED 735
AED 1,223 total
includes taxes & fees
27 Sep - 28 Sep
High Street | Walk to Everything Crozet | Pet-Friendly
Outdoor dining

13. Secluded 20+ Acre Retreat Near Brew & Wine Trails

Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton
9.8 out of 10, Exceptional, (26 reviews)
"Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! "
United States
Harold R.
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Dining

14. Rockwell Ridge | Private Retreat w/ Mountain Views

Rockwell Ridge | Private Retreat w/ Mountain Views
Afton
The price is AED 433
AED 2,631 total
includes taxes & fees
6 Oct - 7 Oct
Rockwell Ridge | Private Retreat w/ Mountain Views
Exterior

15. 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 AED 731
AED 1,339 total
includes taxes & fees
13 Oct - 14 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards
Interior

16. 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.
Rosé All Day: Wine Country Getaway! Walk to Dining
Terrace/patio

17. 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 AED 575
AED 1,243 total
includes taxes & fees
4 Oct - 5 Oct
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Exterior

18. 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 AED 240
AED 619 total
includes taxes & fees
6 Oct - 7 Oct
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Cottage, Private Bathroom (Bluebird Cottage) | Exterior

19. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is AED 422
AED 990 total
includes taxes & fees
28 Sep - 29 Sep
Bluebird Cottage
Exterior

20. 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, (65 reviews)
"Lovely, charming home."
United States
Deborah R.
The price is AED 716
AED 1,218 total
includes taxes & fees
5 Oct - 6 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.
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

Oakhurst Inn at the University

Oakhurst Inn at the University

10/10 Excellent
"My husband and I have stayed here several times and love it!!"
Hannah 1-night trip
Posted 15 hours ago
Oakhurst Inn at the University

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.