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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Greenwood vacation rentals

Standard Suite, 1 Queen Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (63 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is ￥12,762
￥14,205 total
includes taxes & fees
Jul 8 - Jul 9
Affordable Suites of America Waynesboro
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (245 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is ￥15,768
￥17,550 total
includes taxes & fees
Jun 30 - Jul 1
Valley Extended Suites
House, Private Bathroom (Afton Bliss) | Exterior

The Reserve at 151

The Reserve at 151
2.0 star property
Afton
The price is ￥43,780
￥99,056 total
includes taxes & fees
Jun 26 - Jun 27
The Reserve at 151
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (18 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is ￥20,691
￥32,942 total
includes taxes & fees
Jul 1 - Jul 2
Love Ridge Mountain Lodging
Luxury Apartment, Multiple Beds, Non Smoking, Garden View | Egyptian cotton sheets, premium bedding, memory foam beds

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (1 review)
"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 ￥18,490
￥21,133 total
includes taxes & fees
Jun 29 - Jun 30
SONSAK - MONTICELLO
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (116 reviews)
"Great location"
United States
Chrissy R.
The price is ￥27,226
￥53,465 total
includes taxes & fees
Jun 28 - Jun 29
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Exterior detail

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (70 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 ￥24,266
￥39,346 total
includes taxes & fees
Jun 28 - Jun 29
Stay in Crozet Train Suite in Downtown Crozet
Property grounds

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (156 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
The price is ￥17,771
￥39,915 total
includes taxes & fees
Jul 12 - Jul 13
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (106 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is ￥21,002
￥31,750 total
includes taxes & fees
Jul 2 - Jul 3
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (110 reviews)
"The house was very centrally located in Crozet, an easy walk to restaurants and the brewery. It was very cosy and had lots of little extras like coffee and dog treats! We were there for one night for the walk through for our daughters wedding at one of the local vineyards and it was perfect for our needs. "
United States
Helen S.
The price is ￥32,310
￥53,798 total
includes taxes & fees
Jul 7 - Jul 8
High Street | Walk to Everything Crozet | Pet-Friendly
1 bedroom, desk, internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (45 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is ￥24,589
￥49,595 total
includes taxes & fees
Jun 29 - Jun 30
Panoramic Peak: Wintergreen Condo with Views
Outdoor dining

Total Privacy - H’Owl at the Moon Farm & Cabin

Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler
10.0 out of 10, Exceptional, (184 reviews)
"The cabin was amazing. It was so peaceful and quiet. The cabin was in a prefect place to view wildlife and trails to view the additional property. The amenities were great and everything worked as expected. The owner was responsive and very nice. Would stay here again. "
United States
Nova G.
The price is ￥34,360
￥65,530 total
includes taxes & fees
Jul 12 - Jul 13
Total Privacy - H’Owl at the Moon Farm & Cabin
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (54 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is ￥12,579
￥34,109 total
includes taxes & fees
Jun 29 - Jun 30
Where the Trail Ends
Exterior

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (81 reviews)
"The cabin was very clean. Very cozy. We definitely enjoyed our time there and would love to come back."
United States
jeramy p.
The price is ￥30,533
￥56,874 total
includes taxes & fees
Jul 1 - Jul 2
Ivy Rose Cottage nestled b/t Cville & Vineyards
Property grounds

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (108 reviews)
"Nice place!"
United States
Gregory G.
Endless Mountain Top Views from All The Way Up!
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (30 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is ￥24,717
￥52,429 total
includes taxes & fees
Jul 7 - Jul 8
The Cottage @ Afton Mountain- Close to Wineries!
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (35 reviews)
"Condo was as advertised, perfect for a quick trip up to Wintergreen!"
United States
Jason L.
The price is ￥19,491
￥43,478 total
includes taxes & fees
Jun 30 - Jul 1
Wintergreen Condo -Steps to Ski and restaurants

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (324 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is ￥17,762
￥42,657 total
includes taxes & fees
Jul 1 - Jul 2
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Outdoor dining

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is ￥18,756
￥41,746 total
includes taxes & fees
Jun 28 - Jun 29
Escape to the Blue Ridge Mountains at Wine-tergreen!
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (66 reviews)
"Such a great little place! Quick drive to town, but far enough for a quiet night. Room had everything we needed (and then some) for a short stay, and all the animals were the sweetest added bonus. Would absolutely stay here again if we’re ever back in the area."
United States
Rebekah
The price is ￥13,395
￥18,510 total
includes taxes & fees
Jun 29 - Jun 30
The Firefly Springhouse
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

Sleep Inn Staunton

Sleep Inn Staunton

10/10 Excellent
"Clean, quiet and comfortable"
Elizabeth 1-night trip
Posted 7 hours ago
Sleep Inn Staunton

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

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?

Beautiful New Townhome with Mountain Views. Close to downtown!: This vacation home rental near Greenwood offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 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 garden, 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 Charlottesville Ice Park, 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.