Greenwood Vacation Rentals from CA $179: Short-Term Rentals for 2026

Q: 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.

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Our top choices for Greenwood vacation rentals

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

1. Guesthouse

Crozet

Laurie R.

CA $334 total

includes taxes & fees

Nov 10 - Nov 11

A narrow hallway with beige walls, a wooden floor, and a star decoration on the wall.

2. Stay in Crozet Mountain Suite in Downtown Crozet

Crozet

Lynn K.

CA $370 total

includes taxes & fees

Nov 10 - Nov 11

3. Valley Extended Suites

Fishersville

Jamie

CA $179 total

includes taxes & fees

Nov 10 - Nov 11

4. Stay in Crozet Train Suite in Downtown Crozet

Crozet

James B.

CA $370 total

includes taxes & fees

Nov 29 - Nov 30

A cafe interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

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

Crozet

karen r.

CA $507 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a table and chairs, surrounded by lush greenery.

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

Charlottesville

Fay

CA $221 total

includes taxes & fees

Nov 10 - Nov 11

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!

Afton

Mary R.

CA $411 total

includes taxes & fees

Nov 16 - Nov 17

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

Afton

Travis W.

CA $331 total

includes taxes & fees

Nov 10 - Nov 11

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

Crozet

Sam B.

CA $607 total

includes taxes & fees

Nov 10 - Nov 11

A cozy cabin interior with wooden walls, a TV on a wooden stand, a sofa, and a staircase.

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

Afton

Kevin

CA $383 total

includes taxes & fees

Nov 10 - Nov 11

A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

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

Charlottesville

Joel F.

CA $456 total

includes taxes & fees

Nov 10 - Nov 11

A hot tub on a wooden deck with a wooden railing and a table with chairs.

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

Afton

Liz D.

CA $473 total

includes taxes & fees

Nov 12 - Nov 13

A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

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

Charlottesville

Allison H.

CA $381 total

includes taxes & fees

Nov 16 - Nov 17

A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

14. Petite Pink Cottage, Perfect for Solo Travelers

Charlottesville

Tracy

CA $638 total

includes taxes & fees

Nov 10 - Nov 11

A two-story house with a porch, a front door, and a mailbox.

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

Charlottesville

Ron C.

CA $273 total

includes taxes & fees

Nov 10 - Nov 11

A hallway with a wooden floor, a patterned rug, a wooden bench, a chair, a wooden cabinet, and a door with windows.

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

Afton

Dustin S.

CA $1,460 total

includes taxes & fees

Nov 14 - Nov 15

A spacious kitchen with a large island, dark cabinetry, and a stone pendant light.

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

Afton

Maura F.

CA $768 total

includes taxes & fees

Nov 10 - Nov 11

A compact kitchen with white cabinetry, a blue door, and a white refrigerator.

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

Ivy

Linda W.

CA $322 total

includes taxes & fees

Dec 1 - Dec 2

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!

Waynesboro

Elisa G.

CA $252 total

includes taxes & fees

Nov 10 - Nov 11

20. Charming Cottage Near Vineyards

Charlottesville

Nicole M.

CA $864 total

includes taxes & fees

Nov 29 - Nov 30

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Top Greenwood Hotel Reviews

Hotel 24 South

10/10 Excellent

"It’s a beautiful old hotel, and the staff are lovely. It is our go to place in Staunton."

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent

"My only regret was that I couldn’t stay longer. The staff were professional, clear communicators and friendly. The room was clean and neat and the hotel was in a good location. I also very much appreciated that there was a Bible in the room. Prior to reading the entire Bible, it meant little to me whether there was one in a hotel room or not. Now that I’ve read it, it’s indispensable."

Holiday Inn Charlottesville-Monticello by IHG

10/10 Excellent

"The room was very well thought out and had everything I needed. It was very clean and exceptionally quiet. The environmental unit was by far the best, easy to set and extremely quiet. The complimentary breakfast was well above average. I would definitely stay here again."

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood vacation rentals we have selected for you start as low as CA $179 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 vacation 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 vacation.

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 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.

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Check prices for these dates

Our top choices for Greenwood vacation rentals

1. Guesthouse

2. Stay in Crozet Mountain Suite in Downtown Crozet

3. Valley Extended Suites

4. Stay in Crozet Train Suite in Downtown Crozet

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

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

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

8. Willow Haven: Cozy cabin in delightful Afton

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

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

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

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

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

14. Petite Pink Cottage, Perfect for Solo Travelers

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

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

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

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

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

20. Charming Cottage Near Vineyards

Find vacation rentals that suit your style

Top Greenwood Hotel Reviews

Hotel 24 South

Sonesta ES Suites Charlottesville University

Days Inn by Wyndham Charlottesville/University Area

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

DoubleTree by Hilton Hotel Charlottesville

Holiday Inn Charlottesville-Monticello by IHG

Find out more about Greenwood

Frequently asked questions

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