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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Greenwood cottages

A single-story house with a green exterior and a white porch.

1. High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (113 reviews)
"This cute home was perfect for our stay in Crozet! It was close to lovely coffee shops. The home was very clean and communication with the host was fantastic! We would stay here again if in the area."
United States
Jody L.
The price is £251
includes taxes & fees
30 Aug - 31 Aug
High Street | Walk to Everything Crozet | Pet-Friendly
A wooden deck with a round table and chairs, a grill, and a trash can.

2. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was fantastic! Great location for wineries and hiking. Perfect for a couples getaway for privacy and quaintness. Will definitely consider booking again if we ever come back to the area!! "
United States
Liz D.
The price is £252
includes taxes & fees
30 Aug - 31 Aug
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

3. 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, (64 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is £216
includes taxes & fees
30 Aug - 31 Aug
Unique Cypress cottage, close to Charlottesville with mountain views.
A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

4. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (18 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is £127
includes taxes & fees
7 Sept - 8 Sept
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A bathroom with white subway tiles, a window with white curtains, a framed picture on the wall, and a showerhead.

5. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (53 reviews)
"House was quiet and peaceful. We enjoyed our stay. "
United States
Chris R.
The price is £147
includes taxes & fees
1 Sept - 2 Sept
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
A house surrounded by trees with a clear sky.

6. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is £202
includes taxes & fees
30 Aug - 31 Aug
Artisan's Cottage
A two-story house with a porch, a front door, and a mailbox.

7. Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
9.2 out of 10, Wonderful, (7 reviews)
"Such a cozy, secluded cottage! Great place to hang with my besties. We really enjoyed our time at Wandering Bear. "
United States
Carol F.
The price is £155
includes taxes & fees
2 Sept - 3 Sept
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A two-story white house with a front porch, a staircase, and a small front yard.

8. Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries

Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
Charlottesville
10.0 out of 10, Exceptional, (3 reviews)
"We had an absolutely wonderful stay! The property itself was beautiful, comfortable, and everything we could have hoped for, but what really stood out was the owners. Their communication, hospitality, and attention to detail made the entire experience feel effortless. They were incredibly responsive and welcoming from start to finish.It’s clear they take a lot of pride in the property and genuinely care about their guests having a great experience. We would absolutely stay here again and highly...
United States
Alex P.
The price is £283
includes taxes & fees
16 Sept - 17 Sept
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
A single-story house with a front porch, a chimney, and a gravel driveway.

9. Artisan's Cottage: Woodsy+Private, Central to 151

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is £231
includes taxes & fees
30 Aug - 31 Aug
Artisan's Cottage: Woodsy+Private, Central to 151
A covered porch with two wooden chairs and a table, large windows, and a string of lights.

10. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is £478
includes taxes & fees
29 Aug - 30 Aug
Modern Nellysford Getaway on 40 Private Acres!
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

11. Classic Virginia Cottage, 10 min to UVA and Vineyards

Classic Virginia Cottage, 10 min to UVA and Vineyards
Charlottesville
The price is £374
includes taxes & fees
29 Aug - 30 Aug
Classic Virginia Cottage, 10 min to UVA and Vineyards
A rustic wooden cabin with a sloped roof, surrounded by trees and a fenced area.

12. Hike in Shenandoah National Park!

Hike in Shenandoah National Park!
Port Republic
9.8 out of 10, Exceptional, (125 reviews)
"Very comfortable and clean accommodations. The little village was very quiet and close to everything we planned to do in the Shenandoah Valley and National Park. Great communication by Jena. Highly recommend."
United States
Whitney R.
The price is £126
includes taxes & fees
1 Sept - 2 Sept
Hike in Shenandoah National Park!
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

13. Dog Friendly Cottage Close to UVA

Dog Friendly Cottage Close to UVA
Charlottesville
10.0 out of 10, Exceptional, (5 reviews)
"Property was very clean and exactly what we needed. Location is perfect to explore wineries and breweries in both directions. Entrance does sneak up on you at night but no biggie! "
United States
Eric W.
The price is £374
includes taxes & fees
31 Aug - 1 Sept
Dog Friendly Cottage Close to UVA
A two-story house with a large lawn, surrounded by mature trees and a white picket fence.

14. The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!

The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Staunton
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful visit. Beautifully landscaped and, clean property. Peaceful- hope to visit again."
United States
Pam W.
The price is £184
includes taxes & fees
31 Aug - 1 Sept
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
A modern house with a covered patio, outdoor seating, and a well-maintained lawn.

15. Charming Eastham Guesthouse

Charming Eastham Guesthouse
Charlottesville
10.0 out of 10, Exceptional, (11 reviews)
"Great place we loved it! "
United States
Al B.
The price is £167
includes taxes & fees
31 Aug - 1 Sept
Charming Eastham Guesthouse
A two-story house with a wooden deck and a stone border.

16. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is £305
includes taxes & fees
30 Aug - 31 Aug
Little Haven Cottage
A rural landscape with a large house, a fenced yard, and a dirt road.

17. Little Haven Cottage: Walk to Meade Tasting

Little Haven Cottage: Walk to Meade Tasting
Afton
6.0 out of 10, (1 review)
"House was clean except for the two dirty hand towels lying on the bed when we arrived. Washer and dryer were behind a locked door so I had to message the host to get a code to open it. She first insisted it wouldn’t be inside a locked door, so I had to wait for her to find out about it and she replied quickly enough with the access code. I’m guessing nobody ever needed to use the washer before us? Strange. Rooms could have used dressers or something to put clothes in. Vanities in master...
United States
Anonymous traveller
The price is £346
includes taxes & fees
30 Aug - 31 Aug
Little Haven Cottage: Walk to Meade Tasting
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

18. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (7 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is £441
includes taxes & fees
20 Sept - 21 Sept
Charming Cottage Near Vineyards
A blue house with solar panels on the roof, a small patio with a white umbrella, and a garden with red foliage.

19. Locust Garden, A North Downtown C'ville Guesthouse

Locust Garden, A North Downtown C'ville Guesthouse
Locust Grove
8.0 out of 10, Very good, (1 review)
"Very clean and sweet property. Attractively furnished. Check in was easy. Good communication.Kitchen was very easy to use. Did lots of our own cooking. Would have appreciated some quality stainless steel pots and tops as we can’t use anodized cookware for specific health reasons."
United States
Susan K.
The price is £253
includes taxes & fees
1 Sept - 2 Sept
Locust Garden, A North Downtown C'ville Guesthouse
A deck with a fire pit, wooden chairs, and a view of the forest.

20. Mountain Mindset: Pup Friendly + Trail

Mountain Mindset: Pup Friendly + Trail
Laurel Ridge
9.6 out of 10, Exceptional, (10 reviews)
"Nice cabin in a good location! "
United States
Caine C.
The price is £570
includes taxes & fees
30 Aug - 31 Aug
Mountain Mindset: Pup Friendly + Trail
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

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent
"Great"
Jarmy 1-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Greenwood

Greenwood Cottages information

Number of reviews
435
Accommodation
132 Cottages
Lowest Price
£126
Highest Price
£570

Frequently asked questions

How much do cottages in Greenwood cost?
Cottages in Greenwood range between £126 and £570 per night. These retreats offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Greenwood?
Enjoy nature's beauty in one of the 132 cottages available in Greenwood. To help you select an ideal place, use our filter tool to search for amenities or perks you prefer.
Why book your cottage in Greenwood with Expedia?
We think that holidays should be stress-free, so if you're searching for cottages in Greenwood at an affordable rate, Expedia has you covered. Save cash and go for a wallet-friendly option far away from the hustle and bustle, or splurge on a luxury cottage to spoil your loved ones.
How can I find cheap cottages in Greenwood?
With Expedia's filter tool, scoring cheap cottages in Greenwood is a cinch. To find properties that'll make your bank balance smile, narrow your search by amenities, budget and star rating.
What is there to do in Greenwood near my cottage?
If you'd like to discover the sights of Greenwood, pay a visit to Pollak Vineyards. It's a favourite with locals and visitors alike.