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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Greenwood vacation rentals

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

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (93 reviews)
"Great stay! Perfect location, booked for quick overnight girls trip."
United States
Melissa G.
$218 nightly
The price is $249
Oct 20 - Oct 21
Total with taxes and fees
Guesthouse
Street view

2. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (267 reviews)
"Location extremely convenient."
United States
michael
$97 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
Valley Extended Suites
A bedroom with a bed, a ceiling fan, a window with curtains, and a view of greenery outside.

3. Rockwell Ridge | Inn with Afton Mountain Views

Rockwell Ridge | Inn with Afton Mountain Views
Afton
$346 nightly
The price is $371
Nov 3 - Nov 4
Total with taxes and fees
Rockwell Ridge | Inn with Afton Mountain Views
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

4. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (43 reviews)
"Great little cabin"
United States
Travis W.
$221 nightly
The price is $248
Oct 18 - Oct 19
Total with taxes and fees
Willow Haven: Cozy cabin in delightful Afton
A wooden deck with a table and chairs, surrounded by lush greenery.

5. 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, (66 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
$145 nightly
The price is $166
Oct 18 - Oct 19
Total with taxes and fees
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
A blue door with a keyhole and a sign for 'Stay in Crozet' overnight lodging.

6. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (130 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
$227 nightly
The price is $244
Oct 25 - Oct 26
Total with taxes and fees
Stay in Crozet Mountain Suite in Downtown Crozet
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)
"A fun place to stay with room to spread out at the table and large couch, located in the middle of Crozet center in walking distance to churches, 3 unique coffee shops, restaurants and grocery store. Plus short drive to local vineyards, and hiking."
United States
Denise C.
$227 nightly
The price is $244
Oct 19 - Oct 20
Total with taxes and fees
Stay in Crozet Train Suite in Downtown Crozet
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.

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (22 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
$153 nightly
The price is $169
Oct 21 - Oct 22
Total with taxes and fees
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a forested area.

9. Rockwell Ridge | Private Retreat w/ Mountain Views

Rockwell Ridge | Private Retreat w/ Mountain Views
Afton
$796 nightly
The price is $859
Nov 9 - Nov 10
Total with taxes and fees
Rockwell Ridge | Private Retreat w/ Mountain Views
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

10. 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.
$169 nightly
The price is $188
Oct 20 - Oct 21
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A cozy cabin interior with wooden walls, a TV on a wooden stand, a sofa, and a staircase.

11. 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, (17 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.
$255 nightly
The price is $286
Oct 19 - Oct 20
Total with taxes and fees
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.

12. 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.
$293 nightly
The price is $329
Oct 21 - Oct 22
Total with taxes and fees
The Cottage @ Afton Mountain- Close to Wineries!
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)
"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.
$312 nightly
The price is $335
Oct 21 - Oct 22
Total with taxes and fees
High Street | Walk to Everything Crozet | Pet-Friendly
A hot tub on a wooden deck with a wooden railing and a table with chairs.

14. 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.
$310 nightly
The price is $340
Nov 3 - Nov 4
Total with taxes and fees
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

15. 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, (34 reviews)
"Fantastic stay. Happy to return next time."
United States
Sam B.
$391 nightly
The price is $447
Oct 25 - Oct 26
Total with taxes and fees
Rosé All Day: Wine Country Getaway! Walk to Dining
An outdoor dining area with wicker chairs, a table with plates and glasses, a fire pit, and a barbecue grill.

16. 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)
"This is a beautiful, peaceful and quiet spot for retreating! Loved sharing this spot with our family!"
United States
Phyllis A.
$334 nightly
The price is $375
Oct 19 - Oct 20
Total with taxes and fees
Secluded 20+ Acre Retreat Near Brew & Wine Trails
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

17. 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, (67 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
$257 nightly
The price is $294
Nov 12 - Nov 13
Total with taxes and fees
Unique Cypress cottage, close to Charlottesville with mountain views.
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.
$223 nightly
The price is $255
Oct 19 - Oct 20
Total with taxes and fees
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

19. 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, (64 reviews)
"Love this home!! Great backyard, lovely decor and super cozy. Easy access to surrounding attractions."
United States
Kathleen
$185 nightly
The price is $206
Oct 26 - Oct 27
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

20. 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
$316 nightly
The price is $361
Oct 19 - Oct 20
Total with taxes and fees
Ivy Rose Cottage nestled b/t Cville & Vineyards
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

8/10 Good
"I had a really nice stay at the English Inn. The staff were super friendly and helpful. The room was clean, and the corridors were quiet. The hot breakfast was an added bonus after a late night. Everything looked well-maintained, and the touches of England were delightful, including the phone booth in the lobby! I struggled a little with the room temperature when I first arrived, and the refrigerator kept making a clicking noise that made me a little crazy when I was trying to sleep, but overall, it was a very pleasant experience. I hope to return with the rest of my family at some point in the future!"
Saralynn 1-night trip
Posted 2 hours ago
English Inn of Charlottesville

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.