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Compare 122 Cottages in Greenwood with updated reviews, rates, and availability.

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

10.0 out of 10, Exceptional, (44)
"This cottage was in a charming location with a creek out back, lovely grounds, and total privacy. We stayed in the late fall; it must be even better in the spring or summer. It is the best-equipped -i.e., amenities - of any place we’ve ever stayed. Comfortably furnished. Nice appliances. Would happily return. "
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (22)
"Three couples enjoyed this well appointed home….plenty of room and beautiful views. It was convenient to some great restaurants and wineries. We definitely will visit this area again!"
The price is SAR 548
SAR 1,556 total
includes taxes & fees
19 Mar - 20 Mar
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (25)
"Really enjoyed our stay at this unique property, it is very pretty cottage in a nice area. Stayed here with my wife and parents to attend a wedding in Crozet. Very close to Monticello and some very cool walking trails. The host were very responsive and accommodating."
The price is SAR 551
SAR 1,046 total
includes taxes & fees
19 Mar - 20 Mar
Unique Cypress cottage, close to Charlottesville with mountain views.

Cowboy hide-a-way cottage with hot tub on historic farm close to everything

9.4 out of 10, Exceptional, (19)
"We booked this last min. to come see our new grand daughter. It was exactly what we needed and worked out perfect for our short stay!"
Cowboy hide-a-way cottage with hot tub on historic farm close to everything

"The Sparrow" at Historic Downtown Staunton

9.8 out of 10, Exceptional, (13)
"Adorable house, lovely host, wonderful location."
"The Sparrow" at Historic Downtown Staunton

Pine Cottage: Hot Tub and Central to Nelson 151

10.0 out of 10, Exceptional, (18)
"Perfect friends get away! The house is gorgeous and in a perfect location for having an amazing weekend!"
The price is SAR 746
SAR 1,773 total
includes taxes & fees
9 Apr - 10 Apr
Pine Cottage: Hot Tub and Central to Nelson 151

The Cottage @ Afton Mountain- Close to Wineries!

9.8 out of 10, Exceptional, (10)
"Perfect house and location for our group of 4 ladies. We were close to many wineries and breweries and also an easy drive to Wintergreen. "
The price is SAR 664
SAR 1,335 total
includes taxes & fees
19 Mar - 20 Mar
The Cottage @ Afton Mountain- Close to Wineries!

Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country

10.0 out of 10, Exceptional, (2)
"Beautiful view, close to all the wineries and breweries and a short drive into town. "
The price is SAR 484
SAR 1,268 total
includes taxes & fees
7 Apr - 8 Apr
Mountain View Meadow Cottage - Blue Ridge Mountains and Virginia wine country

Last chance to ski Massanutten March Special, just $99/night 2 night minimum

9.8 out of 10, Exceptional, (90)
"I stayed here for a quick overnight stop during my ski trip and it was perfect for what I needed. I arrived around 8 PM and left by checkout time. The two bedroom unit was spacious and comfortable with my room being well decorated and featuring a huge bathroom. The bed was super comfy, and the vanity was great for getting ready. The only thing I suggest is adding a mirror in the second room as my friend noticed it was a bit lacking and decoration. The shower in my room was large with two shower...
Last chance to ski Massanutten March Special, just $99/night 2 night minimum

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (42)
"In the area to see family in Crozet and the cottage was the perfect place for us. The location is so peaceful and quiet. The host were excellent in communication and made us feel truly welcomed. We will stay again when we are back in the area."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

Mechum Hill Cottage: Central to Crozet & Cville

9.0 out of 10, Wonderful, (8)
"Generally good. Very clean, nicely appointed. The owner was very accommodating. Lovely location. The king bed needs to be relocated so that the second person doesn’t have to crawl across the first to get in & out of bed. Bedside tables on both sides would be helpful - need a place to lay the phone at night. There should be a couple of hooks in the bathroom for wet towels or clothes when showering. A second end table on the couch would be a plus. A microwave would be handy for reheating...
The price is SAR 484
SAR 1,033 total
includes taxes & fees
19 Mar - 20 Mar
Mechum Hill Cottage: Central to Crozet & Cville

Birds and Bees Cottage

10.0 out of 10, Exceptional, (40)
"Our hiking trip to Shenandoah Nat park was unexpectedly enhanced by our stay at Birds and Bees cottage! What a lovely, comfortable place with amazing view of the Blue Ridge Mountains and acres of pastures. The turkeys and llamas were so interesting to watch. I particularly liked when the turkeys gobbled in unison! The owners were very nice and informative. Would definitely stay again and recommend."
Birds and Bees Cottage

Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts

10.0 out of 10, Exceptional, (3)
"Great place"
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts

Rosé All Day: Wine Country Getaway! Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (10)
"We were in town for work and needed a comfortable place to come back to at the end of our long days. The beds were extremely comfortable, and the hosts were so responsive! Such a charming house with a great location! We would love to stay again!"
The price is SAR 810
SAR 1,642 total
includes taxes & fees
28 Mar - 29 Mar
Rosé All Day: Wine Country Getaway! Walk to Dining

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!

Pet-Friendly Somerset Cottage at Ivy Cottages

Pet-Friendly Somerset Cottage at Ivy Cottages

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (71)
"We absolutely loved our stay here! Absolutely beautiful property inside and out, perfect cozy spot, caught the snow which was beautiful! Only 15 minutes from town. We will definitely be back, and we loved the Alley Light suggestion from the owner which was incredible! All around it was a perfect stay, thank you!"
1802 cottage once part of Monticello and owned by Thomas Jefferson

Quiet Blue Ridge Mountain Cottage

9.6 out of 10, Exceptional, (82)
"This is a delightful, quiet & clean little cabin. We enjoyed exploring the area then cooking dinner at home and spending time together. Thank you!"
Quiet Blue Ridge Mountain Cottage

Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

10.0 out of 10, Exceptional, (13)
"A great house in a great location! Really big fenced in yard that the dogs loved. This house was more equipped/stocked than any other VRBO we have ever been to- you can tell the owners really care about visitors. Nice quiet location where you can hear the stream if you open the windows. Comfortable beds, very clean- great amenities! Can’t wait to stay here again."
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

The Firefly Cottage

9.8 out of 10, Exceptional, (28)
"Quaint and quiet property. Convenient to Staunton, yet away from the traffic. Perfect spot from which to get to downtown for shopping, dining, etc., and also easy access to the interstate. Highly recommend. "
The Firefly Cottage
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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Other property types in Greenwood

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

9.0 out of 10, Wonderful, (267)
"The date of my stay was Sun Feb 9 - Tues Feb 11, 2025. It was a great place to stay with beautiful views. Our stay was short. We were there for my son to participate in WASI- Wintergreen Alpine Special Invitational. Travel to the Mountain Inn for ski competition and celebration was easy. I really enjoyed having the full kitchen so we could make breakfast each day. The washer and dryer were helpful for keeping ski bibs clean and dry."
The price is SAR 394
SAR 906 total
includes taxes & fees
19 Mar - 20 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (175)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is SAR 406
SAR 452 total
includes taxes & fees
13 Apr - 14 Apr
Valley Extended Suites

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (297)
"Our girls getaway was perfect! The house was just as described and very clean!!! I’m a stickler for clean and every nook and cranny was spotless. There was only one tiny inconvenience with the hot hub not being filled quite enough and maybe not cleaned before we came because of a film on the surface. But the owner/host responded immediately. We had everything we needed to fix the issue. The house is in a perfect location and located on a cul de sac, so very private. Would highly recommend and we...
The price is SAR 559
SAR 1,398 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
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.

Frequently asked questions

How much do cottages in Greenwood cost?
Cottages in Greenwood range between SAR 484 and SAR 810 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 122 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 vacations 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.