Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Greenwood vacation rentals

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, (16 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is ￥19,357
￥31,089 total
includes taxes & fees
Feb 5 - Feb 6
Love Ridge Mountain Lodging
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (217 reviews)
"Clean room great location quiet area"
United States
Krista
The price is ￥16,167
￥17,994 total
includes taxes & fees
Feb 15 - Feb 16
Valley Extended Suites
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (105 reviews)
"Such a lovely cottage in a great spot!We enjoyed Crozet and time at Praha bakery, Star Hill Brewery, King Family Vineyard, and Mint Springs Park!"
United States
Polly H.
The price is ￥31,166
￥51,893 total
includes taxes & fees
Feb 5 - Feb 6
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior

Shenandoah Mansion

Shenandoah Mansion
Elkton
10.0 out of 10, Exceptional, (6 reviews)
"The house was amazing and very cozy. My family enjoyed the amenities that come with the property. I would visit again."
United States
Jansenia Diane
The price is ￥18,855
￥136,250 total
includes taxes & fees
Feb 10 - Feb 11
Shenandoah Mansion
Luxury Room, Ensuite (The Storefront) | Lounge

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great place to stay in charming Staunton!"
United States
Kate
The price is ￥23,171
￥35,282 total
includes taxes & fees
Feb 11 - Feb 12
The Storefront
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (24 reviews)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is ￥29,391
￥72,301 total
includes taxes & fees
Feb 24 - Feb 25
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
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, (47 reviews)
"Great cottage. Very comfortable and good location."
United States
Paul W.
The price is ￥22,860
￥44,081 total
includes taxes & fees
Feb 5 - Feb 6
Unique Cypress cottage, close to Charlottesville with mountain views.
Property grounds

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is ￥27,836
￥64,791 total
includes taxes & fees
Feb 5 - Feb 6
Hillside Haven: Modern Retreat, Mountain Views
Exterior detail

Bee Mountain Cabin fireplace, kitchen, jacuzzi

Bee Mountain Cabin fireplace, kitchen, jacuzzi
Lyndhurst
10.0 out of 10, Exceptional, (11 reviews)
"The cabin is lovely and the scenery is beautiful."
United States
Kimmy M.
The price is ￥28,829
￥36,401 total
includes taxes & fees
Feb 5 - Feb 6
Bee Mountain Cabin fireplace, kitchen, jacuzzi
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
9.8 out of 10, Exceptional, (20 reviews)
"Great place"
United States
Beverly
The price is ￥22,299
￥49,018 total
includes taxes & fees
Feb 5 - Feb 6
The Cottage @ Afton Mountain- Close to Wineries!
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, (68 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is ￥23,375
￥37,901 total
includes taxes & fees
Feb 5 - Feb 6
Stay in Crozet Train Suite in Downtown Crozet
Terrace/patio

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
10.0 out of 10, Exceptional, (12 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is ￥21,352
￥49,704 total
includes taxes & fees
Feb 18 - Feb 19
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Fridge, microwave, oven, stovetop

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (41 reviews)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is ￥14,586
￥29,139 total
includes taxes & fees
Feb 5 - Feb 6
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (5 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is ￥14,773
￥43,411 total
includes taxes & fees
Feb 24 - Feb 25
Laurelwood Hollow: Walk to Ski & Swim
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is ￥40,048
￥76,140 total
includes taxes & fees
Feb 10 - Feb 11
Blackwood Chalet
Property grounds

Welcome to the daughter of the stars

Welcome to the daughter of the stars
Mt Crawford
9.8 out of 10, Exceptional, (50 reviews)
"The place was absolutely perfect, inside and out. Location has amazing video.Look forward to the next stay!"
United States
Ed S.
The price is ￥9,797
￥32,590 total
includes taxes & fees
Feb 10 - Feb 11
Welcome to the daughter of the stars
Exterior

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Verona
10.0 out of 10, Exceptional, (59 reviews)
"Great place to stay. "
United States
Kelly H
The price is ￥19,985
￥34,904 total
includes taxes & fees
Feb 5 - Feb 6
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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, (90 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is ￥20,216
￥30,562 total
includes taxes & fees
Mar 5 - Mar 6
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
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, (124 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
The price is ￥20,102
￥41,999 total
includes taxes & fees
Mar 1 - Mar 2
Escape to the Blue Ridge Mountains at Wine-tergreen!
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, (46 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is ￥18,232
￥31,739 total
includes taxes & fees
Feb 12 - Feb 13
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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

Sonesta ES Suites Charlottesville University

Sonesta ES Suites Charlottesville University

10/10 Excellent
"Loved the two bedrooms and two baths. Loved the quiet! So peaceful. No road noise. Staff was friendly and welcoming "
Irene 1-night trip
Posted 2 days ago
Sonesta ES Suites Charlottesville University

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:

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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?

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: This vacation home rental near Greenwood 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 War Fields, 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.