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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Greenwood vacation rentals

Terrace/patio

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (85 reviews)
"The property was as described ..cute.. clean.. and perfect for our overnight stay."
United States
Shelly B.
The price is AED 413
AED 682 total
includes taxes & fees
16 Aug - 17 Aug
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
9.2 out of 10, Wonderful, (67 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is AED 290
AED 323 total
includes taxes & fees
12 Aug - 13 Aug
Affordable Suites of America Waynesboro
Outdoor dining

3. 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, (63 reviews)
"Great setting and very clean and comfortable."
United States
Jeanie F.
The price is AED 459
AED 609 total
includes taxes & fees
11 Aug - 12 Aug
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Exterior detail

4. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (36 reviews)
"It was close to the Shenandoah Skyline entrance and close to Blue Ridge Tunnel."
United States
Ernest
The price is AED 516
AED 926 total
includes taxes & fees
13 Aug - 14 Aug
Willow Haven: Cozy cabin in delightful Afton
Exterior detail

5. Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (71 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 902 total
includes taxes & fees
17 Aug - 18 Aug
Stay in Crozet Train Suite in Downtown Crozet
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, (124 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 906 total
includes taxes & fees
11 Aug - 12 Aug
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, (250 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is AED 419
AED 466 total
includes taxes & fees
11 Aug - 12 Aug
Valley Extended Suites
Coffee/tea maker, full-size fridge, microwave, oven

8. The Barn at Haden near Wineries and C'ville

The Barn at Haden near Wineries and C'ville
Crozet
10.0 out of 10, Exceptional, (129 reviews)
"Location is amazing and the place is so cute! Would definitely stay again! "
United States
Crystal L.
The price is AED 589
AED 1,066 total
includes taxes & fees
11 Aug - 12 Aug
The Barn at Haden near Wineries and C'ville
Exterior detail

9. 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, (22 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
The price is AED 413
AED 689 total
includes taxes & fees
16 Aug - 17 Aug
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Property grounds

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

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (34 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is AED 678
AED 1,347 total
includes taxes & fees
11 Aug - 12 Aug
The Cottage @ Afton Mountain- Close to Wineries!
Coffee/tea maker, fridge, microwave, oven

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

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (52 reviews)
"House was quiet and peaceful. We enjoyed our stay. "
United States
Chris R.
The price is AED 428
AED 800 total
includes taxes & fees
1 Sep - 2 Sep
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Exterior

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (17 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is AED 240
AED 619 total
includes taxes & fees
1 Sep - 2 Sep
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Interior

13. 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, (29 reviews)
"It was an excellent place to stay while in Crozet. Roomy and nice house."
United States
Carolyn R.
The price is AED 484
AED 1,225 total
includes taxes & fees
18 Aug - 19 Aug
Rosé All Day: Wine Country Getaway! Walk to Dining
Outdoor spa tub

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, (59 reviews)
"The hot tub was excellent! Such a cute, cozy, and accommodating weekend!"
United States
Sally A.
The price is AED 430
AED 752 total
includes taxes & fees
13 Aug - 14 Aug
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Exterior

15. 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, (62 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is AED 588
AED 1,104 total
includes taxes & fees
26 Aug - 27 Aug
Unique Cypress cottage, close to Charlottesville with mountain views.
Interior

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

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (112 reviews)
"Great little spot, very close to “downtown” Crozet. Great host, great communication…."
United States
Anonymous traveler
The price is AED 735
AED 1,219 total
includes taxes & fees
1 Sep - 2 Sep
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior

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

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (90 reviews)
"Place was perfect! Was a just right distance from the bustle of Charlottesville!"
United States
Bobby T.
The price is AED 661
AED 1,247 total
includes taxes & fees
20 Aug - 21 Aug
Ivy Rose Cottage nestled b/t Cville & Vineyards
Luxury Apartment, Multiple Beds, Non Smoking, Garden View | Egyptian cotton sheets, premium bedding, memory foam beds

18. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is AED 420
AED 480 total
includes taxes & fees
11 Aug - 12 Aug
SONSAK - MONTICELLO
TV, fireplace, offices

19. The Branch at Afton Mountain Retreat

The Branch at Afton Mountain Retreat
Afton
10.0 out of 10, Exceptional, (38 reviews)
"We loved our 2 night stay at this absolutely perfect property ! The place was decorated so tastefully and was immaculate and clean. Beds were super comfortable and bathrooms were modern and updated. The shower had great water pressure and we especially enjoyed having our morning coffee on the lovely screened in porch. Perfect location for wineries and breweries and a short drive to Charlottesville/UVA. We will definitely return and highly recommend! "
United States
Denise M.
The price is AED 753
AED 1,606 total
includes taxes & fees
11 Aug - 12 Aug
The Branch at Afton Mountain Retreat
Exterior

20. Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (33 reviews)
"The location was great and the place was very nice. "
United States
Amanda L.
The price is AED 398
AED 539 total
includes taxes & fees
16 Aug - 17 Aug
Unit 5 - Cozy Lower Level Studio Suite
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

Boar's Head Resort

Boar's Head Resort

10/10 Excellent
"Staff friendly and all helpful Room clean and kept up every day. Food for the price very tasty. Quick service. I had a wheel chair and ALLWAYS had room while dinning. Will return in our travels. Charlie P"
Charlie 4-night trip
Posted less than an hour ago
Boar's Head Resort

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?

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: Located near Greenwood, this vacation home rental is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.