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Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Greenwood holiday rentals

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 HK$895
HK$1,024 total
includes taxes & fees
21 Jun - 22 Jun
SONSAK - MONTICELLO
Exterior

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 HK$848
HK$1,149 total
includes taxes & fees
21 Jun - 22 Jun
Unit 5 - Cozy Lower Level Studio Suite
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 HK$1,018
HK$1,540 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Shower, hair dryer, towels, soap

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (65 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 HK$649
HK$897 total
includes taxes & fees
29 Jun - 30 Jun
The Firefly Springhouse
Exterior

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
10.0 out of 10, Exceptional, (12 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is HK$581
HK$1,397 total
includes taxes & fees
21 Jun - 22 Jun
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Private kitchen

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (62 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is HK$619
HK$689 total
includes taxes & fees
21 Jun - 22 Jun
Affordable Suites of America Waynesboro
Outdoor spa tub

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, (56 reviews)
"Perfect for what we needed. "
United States
Matt & Jean
The price is HK$1,018
HK$1,744 total
includes taxes & fees
1 Jul - 2 Jul
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Exterior

Unit 3 - Luxury King Suite with Private Balcony

Unit 3 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (26 reviews)
"Very nice space. Clean, quiet, and comfortable. Host very responsive to any questions or information needs. Would definitely consider staying here again."
United States
Brian T.
The price is HK$1,563
HK$2,019 total
includes taxes & fees
17 Jun - 18 Jun
Unit 3 - Luxury King Suite with Private Balcony
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (17 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is HK$1,162
HK$1,775 total
includes taxes & fees
24 Jun - 25 Jun
Love Ridge Mountain Lodging
Property grounds

Cozy cabin for 2 w/ great mt views & walking trails!

Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler
10.0 out of 10, Exceptional, (183 reviews)
"Beautiful cabin, clean, peaceful and quiet! "
United States
Lanelle A.
The price is HK$1,057
HK$1,363 total
includes taxes & fees
17 Jun - 18 Jun
Cozy cabin for 2 w/ great mt views & walking trails!
Exterior

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, (56 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is HK$1,332
HK$2,427 total
includes taxes & fees
30 Jun - 1 Jul
Unique Cypress cottage, close to Charlottesville with mountain views.
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 HK$1,175
HK$1,897 total
includes taxes & fees
17 Jun - 18 Jun
Stay in Crozet Train Suite in Downtown Crozet
Outdoor dining

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, (59 reviews)
"Great little place! I fit our needs perfectly."
United States
Betsy D.
The price is HK$979
HK$1,298 total
includes taxes & fees
22 Jun - 23 Jun
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
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, (155 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 HK$862
HK$1,927 total
includes taxes & fees
17 Jun - 18 Jun
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (53 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 HK$602
HK$1,643 total
includes taxes & fees
30 Jun - 1 Jul
Where the Trail Ends
Fridge, microwave, oven, stovetop

RiverFront Country Home with Blue Mountain Views

RiverFront Country Home with Blue Mountain Views
Free Union
9.8 out of 10, Exceptional, (30 reviews)
"A quiet and clean stopping place out in the country very close to one of the southern entrances to Shenandoah National Park. Would definitely stay again if in the area."
United States
Timothy
The price is HK$642
HK$1,295 total
includes taxes & fees
30 Jun - 1 Jul
RiverFront Country Home with Blue Mountain Views
1 bedroom, iron/ironing board, free WiFi, bed sheets

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is HK$670
HK$1,738 total
includes taxes & fees
17 Jun - 18 Jun
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (29 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is HK$1,135
HK$2,480 total
includes taxes & fees
23 Jun - 24 Jun
The Cottage @ Afton Mountain- Close to Wineries!
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (109 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 HK$1,567
HK$2,600 total
includes taxes & fees
17 Jun - 18 Jun
High Street | Walk to Everything Crozet | Pet-Friendly
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, (183 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 HK$1,833
HK$3,474 total
includes taxes & fees
21 Jun - 22 Jun
Total Privacy - H’Owl at the Moon Farm & Cabin
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

Comfort Inn & Suites Charlottesville Hollymead Town Center

Comfort Inn & Suites Charlottesville Hollymead Town Center

10/10 Excellent
"Clean, comfortable and quiet hotel. Good breakfast also."
Cyndi 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Charlottesville Hollymead Town Center

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 holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

Beautiful New Townhome with Mountain Views. Close to downtown!: This holiday home rental outside of Greenwood offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.