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Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Isolated cottage with good view close to many winery and Brewers.
8.8 out of 10, Excellent, (25)
"The house suited us perfectly for our stay. I grew up in the area and know Greenwood pretty well, so felt like home :-) "
United States
Joseph K.
Isolated cottage with good view close to many winery and Brewers.
The Storefront
3.5 star property
8.8 out of 10, Excellent, (57)
"Great place to stay in charming Staunton!"
United States
Kate
The price is NZ$394
includes taxes & fees
2 Nov - 3 Nov
The Storefront
Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (209)
"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$201
includes taxes & fees
24 Nov - 25 Nov
Valley Extended Suites
Welcome to the daughter of the stars
10.0 out of 10, Exceptional, (44)
"Cute place, had everything we needed. The hammock outside was lovely at night time. Very close to vineyards with grocery store a ~15 minute drive away. Would definitely stay again!"
United States
Cameron
The price is NZ$364
includes taxes & fees
29 Oct - 30 Oct
Welcome to the daughter of the stars
Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
8.0 out of 10, Very good, (8)
"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.
The price is NZ$508
includes taxes & fees
26 Oct - 27 Oct
Bluebird Cottage: Near 151 + Appalachian Trail
Private studio apartment in the heart of Ivy, Virginia
10.0 out of 10, Exceptional, (55)
"Nice little place in a beautiful area. Would definitely stay again if visiting the this part of Virginia. The eggs were our dinner! Very nice!!"
United States
Richard H.
The price is NZ$288
includes taxes & fees
6 Nov - 7 Nov
Private studio apartment in the heart of Ivy, Virginia
Charming Eastham Guesthouse
2.0 star property
10.0 out of 10, Exceptional, (3)
"Lovely spot near Charlottesville, great for families or small groups. Guesthouse was clean and has a nice kitchen. "
United States
Nicholas K.
The price is NZ$387
includes taxes & fees
27 Oct - 28 Oct
Charming Eastham Guesthouse
Guesthouse
10.0 out of 10, Exceptional, (60)
"Very clean and welcoming!"
United States
Betsy D.
The price is NZ$323
includes taxes & fees
31 Oct - 1 Nov
Guesthouse
The Firefly Springhouse
9.8 out of 10, Exceptional, (39)
"What a great place to stay! It is such a cute space, and the owners were wonderful! If you love a farm there are plenty of chickens, goats and even a couple of peacocks! We will definitely be back! It was a perfect for our last minute quick getaway! "
United States
Courtney
The price is NZ$217
includes taxes & fees
17 Nov - 18 Nov
The Firefly Springhouse
Retreat @ 3 Ridges / 8 min to Blue Ridge Parkway
2.0 star property
10.0 out of 10, Exceptional, (21)
"Loved our short stay at the property. Everything was as described. Would stay again."
United States
Stephanie S.
The price is NZ$491
includes taxes & fees
27 Oct - 28 Oct
Retreat @ 3 Ridges / 8 min to Blue Ridge Parkway
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
10.0 out of 10, Exceptional, (39)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is NZ$350
includes taxes & fees
12 Nov - 13 Nov
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
The Shenandoah Suite
2.0 star property
10.0 out of 10, Exceptional, (5)
"Not wanting a stuffy hotel we opted for an apartment type rental. Full kitchen, living room, bedroom and bathroom. Having a couch to feel at home to watch TV made our stay homey. Absolutely loved the decor with a theme throughout the place. I love the charm of the old homes and this one didn’t disappoint. If I get back to Staunton I will definitely stay here! "
United States
Vickie
The price is NZ$280
includes taxes & fees
17 Nov - 18 Nov
The Shenandoah Suite
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
10.0 out of 10, Exceptional, (54)
"Great place to stay. "
United States
Kelly H
The price is NZ$386
includes taxes & fees
26 Oct - 27 Oct
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
The Cottage @ Afton Mountain- Close to Wineries!
10.0 out of 10, Exceptional, (16)
"Great place"
United States
Beverly
The price is NZ$590
includes taxes & fees
27 Oct - 28 Oct
The Cottage @ Afton Mountain- Close to Wineries!
Mechum Hill Cottage: Central to Crozet & Cville
9.6 out of 10, Exceptional, (16)
"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 NZ$487
includes taxes & fees
11 Nov - 12 Nov
Mechum Hill Cottage: Central to Crozet & Cville
The Modern Mountain Condo
10.0 out of 10, Exceptional, (30)
"Ideal location for skiing at Wintergreen. "
United States
Ashok G.
The price is NZ$423
includes taxes & fees
26 Oct - 27 Oct
The Modern Mountain Condo
Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is NZ$474
includes taxes & fees
24 Nov - 25 Nov
Love Ridge Mountain Lodging
Charming Vacation Rental in a Barn on a Horse Farm near Afton Mountain in Virginia
2.0 star property
The price is NZ$440
includes taxes & fees
2 Nov - 3 Nov
Charming Vacation Rental in a Barn on a Horse Farm near Afton Mountain in Virginia
Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!
2.0 star property
The price is NZ$271
includes taxes & fees
27 Oct - 28 Oct
Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
9.8 out of 10, Exceptional, (25)
"Lovely condo. Perfect size for us. Highly recommend, perfect location to go and visit wineries and breweries. Then come back and make a delicious meal or enjoy a beverage on the deck. "
United States
Debbie
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
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, 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 NZ$201 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?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This holiday home rental outside of Greenwood is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.