Greenville Holiday Rentals

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Our top choices for Greenville holiday rentals

Apartment in Fishersville

Valley Extended Suites
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 NZ$219
includes taxes & fees
16 Dec - 17 Dec
Valley Extended Suites
10.0 out of 10, Exceptional, (255)
"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!!

Cabin in Montebello

Love Ridge Mountain Lodging
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 NZ$451
includes taxes & fees
16 Dec - 17 Dec
Love Ridge Mountain Lodging
10.0 out of 10, Exceptional, (45)
"Nice quiet set of new cabins. Solid set of amenities. Really enjoyed our stay."
United States
Jesse C.
The price is NZ$389
includes taxes & fees
16 Dec - 17 Dec
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is NZ$1,853
includes taxes & fees
7 Jan - 8 Jan 2026
New Build! Log Cabin with Hot Tub in Wintergreen

Condo in Wintergreen Resort

Wow! What A View!
10.0 out of 10, Exceptional, (55)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
9.0 out of 10, Wonderful, (303)
"Great view!!"
United States
Suzanne W.
The price is NZ$377
includes taxes & fees
16 Dec - 17 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.8 out of 10, Exceptional, (59)
"Good location. Great view. "
United States
Elizabeth G.
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (34)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
The price is NZ$395
includes taxes & fees
16 Dec - 17 Dec
The Modern Mountain Condo
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 NZ$677
includes taxes & fees
16 Dec - 17 Dec
Afton Mountain Vineyards

Cabin in Vesuvius

Whimsical Creekside Cabin
9.8 out of 10, Exceptional, (40)
"Had a very quiet relaxing stay "
United States
Joyce I.
The price is NZ$295
includes taxes & fees
17 Dec - 18 Dec
Whimsical Creekside Cabin
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is NZ$453
includes taxes & fees
16 Dec - 17 Dec
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Holiday Home in Laurel Ridge

Mountain Views in Wintergreen
10.0 out of 10, Exceptional, (9)
"We had a great trip! The house was beautiful with so much space! We loved using the hot tub at night. The host was helpful and responsive to all my questions. Would be happy to book this house again."
United States
Kara S.
Mountain Views in Wintergreen
10.0 out of 10, Exceptional, (92)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is NZ$453
includes taxes & fees
16 Dec - 17 Dec
Wintergreen. Sunset Vista Villa - Close to the ski slopes
10.0 out of 10, Exceptional, (68)
"Stunning scenic getaway! Perfect setting, beautiful decor, high end amenities, gracious host, serene outdoor spaces. One of best places we’ve stayed. Highly recommend."
United States
Diane L.
The price is NZ$756
includes taxes & fees
18 Dec - 19 Dec
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
10.0 out of 10, Exceptional, (303)
"Large well appointed home. Perfect for our family who likes to hang out and cook together and play games in the evening. Beautiful area! Recommended!"
United States
Kristen S.
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
9.6 out of 10, Exceptional, (29)
"Great place to stay, would book again!"
United States
Jessica P.
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
10.0 out of 10, Exceptional, (336)
"A nice, comfortable ski lodge in a beautiful area."
United States
Christopher B.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Chalet in Wintergreen Resort

Dragon's Back, 9BR 10BA in Wintergreen
The price is NZ$5,587
includes taxes & fees
2 Jan - 3 Jan 2026
Dragon's Back, 9BR 10BA in Wintergreen
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 favorite 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 depends 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 NZ$219 per night. Entering your travel dates in the search wizard you might find 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.