Greenville Holiday Rentals

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Holiday Rentals in Greenville

Apartment in Fishersville

3.0 star property
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is AU$191
includes taxes & fees
9 Dec - 10 Dec
Valley Extended Suites

Cabin in Montebello

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is AU$394
includes taxes & fees
9 Dec - 10 Dec
Love Ridge Mountain Lodging

Condo in Wintergreen

10.0 out of 10, Exceptional, (252)
"Stayed 3 nights for a wedding at Wintergreen. Wonderful place with spectacular views "
United States
Michael S.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!

Cabin in Chestnut Springs

10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is AU$1,552
includes taxes & fees
7 Jan - 8 Jan 2026
New Build! Log Cabin with Hot Tub in Wintergreen

Cabin in Montebello

10.0 out of 10, Exceptional, (44)
"Nice quiet set of new cabins. Solid set of amenities. Really enjoyed our stay."
United States
Jesse C.
The price is AU$350
includes taxes & fees
10 Dec - 11 Dec
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Cabin in Vesuvius

9.8 out of 10, Exceptional, (39)
"Had a very quiet relaxing stay "
United States
Joyce I.
The price is AU$292
includes taxes & fees
9 Dec - 10 Dec
Whimsical Creekside Cabin

Cabin in Afton

2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is AU$592
includes taxes & fees
9 Dec - 10 Dec
Afton Mountain Vineyards

Condo in Roseland

9.0 out of 10, Wonderful, (302)
"Great view!!"
United States
Suzanne W.
The price is AU$341
includes taxes & fees
9 Dec - 10 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Cabin in Montebello

9.8 out of 10, Exceptional, (235)
"The river access is top notch. Great location near a bunch of hikes. A perfect, peaceful spot for a weekend. "
United States
John M.
Rustic Mountain Retreat-Bear Paw

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Condo in Roseland

10.0 out of 10, Exceptional, (336)
"Great stay, highly recommended"
United States
Jeffrey E.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Holiday Home in Pedlars Edge

10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet

Condo in Roseland

9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is AU$381
includes taxes & fees
9 Dec - 10 Dec
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Cabin in Nellysford

10.0 out of 10, Exceptional, (30)
"This location was a nice place to relax and enjoy family time."
United States
Melissa H.
Cozy Cabin with private HOT TUB!

Holiday Home in Roseland

10.0 out of 10, Exceptional, (36)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
Hiker’s paradise! Come relax this summer!!!

Holiday Home in Lexington

9.6 out of 10, Exceptional, (211)
"Wonderful stay!"
United States
Lindsey C.
Alone Mill Schoolhouse - A paradise for outdoor lovers

Holiday Home in Wintergreen Resort

9.8 out of 10, Exceptional, (47)
"Beautiful property, well maintained. Perfect for a large group."
United States
Kenneth H.
The newest and largest edition to the Wintergreen Retreat portfolio!

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (91)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is AU$405
includes taxes & fees
9 Dec - 10 Dec
Wintergreen. Sunset Vista Villa - Close to the ski slopes
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 Greenville Hotel Reviews

Find out more about Greenville

Everything you need to know about Greenville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Greenville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenville holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenville rentals

At Expedia, we put the best Greenville holiday 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 Greenville 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 Greenville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenville. 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 a holiday rental in Greenville?

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

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

Large and Luxurious Exec 5BR Chalet: This holiday home rental outside of Greenville is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Greenville?

Explore the area and family-friendly sights such as Sunspots Studios Glassblowing, or get out into nature at a spot like George Washington National Forest. In the wider area, you’ll find Sherando Lake Recreation Area and Frontier Culture Museum.

What are holiday rentals like in Greenville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenville. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.