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Holiday Rentals in Greenwood

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Holiday Rentals in Greenwood

Cottage in Roseland

2.0 star property
8.4 out of 10, Very good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
Bluebird Cottage: Near 151 + Appalachian Trail

Apartment in Mt Crawford

9.8 out of 10, Exceptional, (47)
"We loved our stay while visiting Shenandoah National Park. It was a great stay! We appreciate how wonderful the communication and beautiful the location was! Very clean! Would absolutely recommend! "
United States
Leah M.
The price is €185
includes taxes & fees
4 Dec - 5 Dec
Welcome to the daughter of the stars

Apartment in Waynesboro

2.5 star property
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is €76
includes taxes & fees
1 Jan - 2 Jan 2026
Affordable Suites of America Waynesboro

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 €225
includes taxes & fees
4 Dec - 5 Dec
Love Ridge Mountain Lodging

Cottage in Charlottesville

9.6 out of 10, Exceptional, (17)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
United States
Steven
The price is €247
includes taxes & fees
14 Dec - 15 Dec
Mechum Hill Cottage: Central to Crozet & Cville

Cottage in Afton

9.8 out of 10, Exceptional, (10)
"Very tranquil place. "
United States
Thomas K.
Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Apartment in Crozet

10.0 out of 10, Exceptional, (67)
"The property was the perfect place for a weekend trip to Crozet! The beds were comfy, the place was beautifully decorated, and the location was ideal. Plus, Joanna was super responsive throughout the entire process. We will definitely keep this lovely guesthouse in mind for future trips! "
United States
MaryJo M.
The price is €164
includes taxes & fees
11 Dec - 12 Dec
Guesthouse

Holiday Home in Jefferson Park Avenue

2.0 star property
10.0 out of 10, Exceptional, (5)
"Was a great place. "
United States
Tripp C.
Westerly Haven B: Walk to Scott Stadium!

Cabin in Roseland

10.0 out of 10, Exceptional, (89)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is €173
includes taxes & fees
4 Dec - 5 Dec
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Holiday Home in Staunton

9.8 out of 10, Exceptional, (43)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
The price is €102
includes taxes & fees
14 Dec - 15 Dec
The Firefly Springhouse

Holiday Home in Waynesboro

10.0 out of 10, Exceptional, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
The price is €151
includes taxes & fees
7 Dec - 8 Dec
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Cottage in Ivy

10.0 out of 10, Exceptional, (40)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Cottage in Crozet

2.0 star property
10.0 out of 10, Exceptional, (18)
"The house was clean, fully stocked kitchen, comfortable beds, nice big full bathroom, and convenient location!"
United States
Margaret W.
Rosé All Day: Wine Country Getaway! Walk to Dining

Cottage in Charlottesville

10.0 out of 10, Exceptional, (45)
"Lovely stay. Clean, comfortable, quaint, and roomy. Perfect location for our family!"
United States
kim E.
The price is €250
includes taxes & fees
4 Dec - 5 Dec
Unique Cypress cottage, close to Charlottesville with mountain views.

Apartment in Charlottesville

10.0 out of 10, Exceptional, (55)
"Good stay."
United States
Aabir K.
The price is €146
includes taxes & fees
4 Dec - 5 Dec
Private studio apartment in the heart of Ivy, Virginia

Cabin in Elkton

10.0 out of 10, Exceptional, (6)
"All the unusual amenities were a nice touch for our group. Would stay here again if we come back for our annual golf trip or if I bring my family back to the area."
United States
jeremy s.
Shenandoah Mansion

Condo in Wintergreen Resort

2.0 star property
10.0 out of 10, Exceptional, (24)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is €272
includes taxes & fees
4 Dec - 5 Dec
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Cabin in Schuyler

10.0 out of 10, Exceptional, (171)
"Gorgeous spot, and the cabin is very cozy and clean and has all the essentials, including smart TV and WiFi! Close to hiking trails, and not a far drive from wineries, breweries and a few restaurants. Sunsets are beautiful out back, and the location is quiet and peaceful."
United States
Lauren
Cozy cabin for 2 w/ great mt views & walking trails!

Holiday Home in Waynesboro

9.6 out of 10, Exceptional, (44)
"We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. "
United States
Virginia W.
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Condo in Charlottesville

10.0 out of 10, Exceptional, (27)
"This VRBO was super clean, great accommodations, and very nice owners."
United States
Elizabeth B.
The price is €113
includes taxes & fees
4 Dec - 5 Dec
Unit 5 - Cozy Lower Level Studio Suite
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

Find out more about Greenwood

Everything you need to know about Greenwood 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 Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Greenwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenwood holiday 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 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 Greenwood 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 Greenwood holiday rentals we have selected for you start as low as €208 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood 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 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 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 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 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?

Large and Luxurious Exec 5BR Chalet: This holiday home rental outside of Greenwood 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.

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 War Fields, or get out into nature at a spot like Shenandoah National Park. 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.