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Our top choices for Greenwood holiday rentals

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
9.8 out of 10, Exceptional, (6 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is £110
includes taxes & fees
12 Apr - 13 Apr
Brand new serene luxury cottage just off the Brew Ridge Trail

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
The price is £108
includes taxes & fees
12 Apr - 13 Apr
SONSAK - MONTICELLO

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (55 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is £88
includes taxes & fees
12 Apr - 13 Apr
The Firefly Springhouse

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (54 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is £69
includes taxes & fees
30 Apr - 1 May
Affordable Suites of America Waynesboro

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, (179 reviews)
"Everything was amazing "
United States
Richard
The price is £143
includes taxes & fees
12 Apr - 13 Apr
Cozy cabin for 2 w/ great mt views & walking trails!

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, (50 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
The price is £220
includes taxes & fees
5 May - 6 May
Unique Cypress cottage, close to Charlottesville with mountain views.

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (14 reviews)
"This house was lovely for our small family. The hot tub, the proximity to ski resort. Highly recommend!"
United States
Megan B.
The price is £240
includes taxes & fees
12 Apr - 13 Apr
Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (106 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is £216
includes taxes & fees
13 Apr - 14 Apr
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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, (98 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is £149
includes taxes & fees
13 Apr - 14 Apr
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

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, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is £143
includes taxes & fees
13 Apr - 14 Apr
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (69 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is £184
includes taxes & fees
12 Apr - 13 Apr
Stay in Crozet Train Suite in Downtown Crozet

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (106 reviews)
"Very clean and amazing location. Owners are very communicative. We certainly plan on returning in the future. "
United States
Anthony C.
The price is £250
includes taxes & fees
12 Apr - 13 Apr
High Street | Walk to Everything Crozet | Pet-Friendly

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (317 reviews)
"I love this place!!! Will book again everytime we are there!"
United States
Thavikiet T.
The price is £191
includes taxes & fees
12 Apr - 13 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (30 reviews)
"The location was great and the place was very nice. "
United States
Amanda L.
The price is £112
includes taxes & fees
12 Apr - 13 Apr
Unit 5 - Cozy Lower Level Studio Suite

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is £174
includes taxes & fees
12 Apr - 13 Apr
The Modern Mountain Condo

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (101 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is £181
includes taxes & fees
12 Apr - 13 Apr
Endless Mountain Top Views from All The Way Up!

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (22 reviews)
"Very clean and central to the wineries."
United States
Cynda
The price is £237
includes taxes & fees
19 Apr - 20 Apr
The Cottage @ Afton Mountain- Close to Wineries!

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, (57 reviews)
"Great little place! I fit our needs perfectly."
United States
Betsy D.
The price is £126
includes taxes & fees
12 Apr - 13 Apr
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is £165
includes taxes & fees
12 Apr - 13 Apr
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

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, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is £188
includes taxes & fees
12 Apr - 13 Apr
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
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 £86 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?

Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive: This holiday home rental outside of Greenwood is located in the city centre, and has a balcony, a selection of games and air conditioning 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.

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 Virginia Discovery Museum, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. 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.