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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Greenwood vacation rentals

Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (68 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
$103 nightly
The price is $114
Jul 18 - Jul 19
Total with taxes and fees
The Firefly Springhouse
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, (2 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
$127 nightly
The price is $145
Jul 19 - Jul 20
Total with taxes and fees
SONSAK - MONTICELLO
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, (49 reviews)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
$165 nightly
The price is $188
Jul 20 - Jul 21
Total with taxes and fees
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Exterior

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, (190 reviews)
"Excellent stay! Perfect little get-a-way cabin in the woods!"
United States
Brenda P.
$146 nightly
The price is $164
Jul 20 - Jul 21
Total with taxes and fees
Cozy cabin for 2 w/ great mt views & walking trails!
Exterior detail

Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.6 out of 10, Exceptional, (34 reviews)
"Great little place! Would stay again!!"
United States
brian f.
$206 nightly
The price is $232
Jul 20 - Jul 21
Total with taxes and fees
Willow Haven: Cozy cabin in delightful Afton
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (57 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.
$190 nightly
The price is $213
Jul 21 - Jul 22
Total with taxes and fees
Where the Trail Ends
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, (108 reviews)
"Beautiful cabin!"
United States
Anna W.
$175 nightly
The price is $197
Jul 19 - Jul 20
Total with taxes and fees
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Standard Suite, 1 Queen Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (65 reviews)
"Very good value, would definitely stay again"
United States
Frank
$81 nightly
The price is $90
Aug 5 - Aug 6
Total with taxes and fees
Affordable Suites of America Waynesboro
Interior

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (31 reviews)
"Everything was perfect! "
United States
Danielle B.
$201 nightly
The price is $226
Jul 22 - Jul 23
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
$220 nightly
The price is $247
Jul 16 - Jul 17
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior detail

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, (21 reviews)
"Great host and beautifully decorated property."
United States
Elisa G.
$169 nightly
The price is $188
Jul 19 - Jul 20
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (31 reviews)
"Well supplied with essentials , charming"
United States
Beth
$282 nightly
The price is $317
Jul 19 - Jul 20
Total with taxes and fees
The Cottage @ Afton Mountain- Close to Wineries!
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, (33 reviews)
"Enjoyed our stay."
United States
Katrecia B.
$143 nightly
The price is $162
Jul 20 - Jul 21
Total with taxes and fees
RiverFront Country Home with Blue Mountain Views
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, (61 reviews)
"Great little place! I fit our needs perfectly."
United States
Betsy D.
$145 nightly
The price is $166
Jul 19 - Jul 20
Total with taxes and fees
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
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, (20 reviews)
"Very quiet and peaceful stay. "
United States
Timika
$212 nightly
The price is $231
Jul 21 - Jul 22
Total with taxes and fees
Love Ridge Mountain Lodging
Fridge, microwave, oven, stovetop

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (41 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$275 nightly
The price is $308
Jul 19 - Jul 20
Total with taxes and fees
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
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.
$128 nightly
The price is $147
Jul 19 - Jul 20
Total with taxes and fees
Unit 5 - Cozy Lower Level Studio Suite
Exterior

Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (85 reviews)
"Very unique and beautiful two story cottage in the woods."
United States
Harvey
$295 nightly
The price is $337
Jul 19 - Jul 20
Total with taxes and fees
Ivy Rose Cottage nestled b/t Cville & Vineyards
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
$229 nightly
The price is $247
Jul 16 - Jul 17
Total with taxes and fees
Stay in Crozet Train Suite in Downtown Crozet
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, (60 reviews)
"We have stayed here once before and we absolutely love the place. Mary is an excellent host and she did everything to accommodate us. "
United States
Kurt K.
$257 nightly
The price is $294
Aug 11 - Aug 12
Total with taxes and fees
Unique Cypress cottage, close to Charlottesville with mountain views.
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

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent
"Personal de primera , muy limpio piscina bien laundry bien este hotel vale la pena"
Carlos Jose Sanchez 2-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

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 $90 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 rental 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 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.