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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Greenwood

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
Escape to a secluded cabin surrounded by lush woods, with a sheltered porch and natural stone entrance.

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

10.0 out of 10, Exceptional, (58)
"Wonderful getaway with beautiful outdoor space! "
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
1802 cottage once part of Monticello and owned by Thomas Jefferson
Relax by the serene pool surrounded by lush greenery and a lawn.

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (79)
"This is a great place to stay. Close to town but out on a large very private farm. Highly recommend. "
1802 cottage once part of Monticello and owned by Thomas Jefferson
Hike in Shenandoah National Park this June!
Situated in a rural setting, this cabin features a traditional design and weathered exterior.

Hike in Shenandoah National Park this June!

9.8 out of 10, Exceptional, (101)
"Booked this property based on its proximity to Grand Caverns. It was perfectly situated netween the cavern, shopping and local wineries. Will definitely book if in the area again "
Hike in Shenandoah National Park this June!
Mechum Hill Cottage: Central to Crozet & Cville
Enjoy serene views of the forest from this outdoor space, perfect for dining or relaxation.

Mechum Hill Cottage: Central to Crozet & Cville

9.4 out of 10, Exceptional, (12)
"The location and very clean cottage"
The price is NZ$463
includes taxes & fees
27 July - 28 July
Mechum Hill Cottage: Central to Crozet & Cville
High Street | Walk to Everything Crozet | Pet-Friendly
Step outside to a cozy porch with a comfortable chair and a welcoming entrance.

High Street | Walk to Everything Crozet | Pet-Friendly

9.8 out of 10, Exceptional, (101)
"Very cute and very clean. Enjoyed our stay. I understand the abandoned area will be upgraded, looking forward to seeing the outcome"
The price is NZ$541
includes taxes & fees
5 Aug - 6 Aug
High Street | Walk to Everything Crozet | Pet-Friendly
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Relax in a serene garden setting with a comfortable seating area featuring two chairs and lush greenery.

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

10.0 out of 10, Exceptional, (35)
"The property was was beautiful, historic and quiet."
The price is NZ$362
includes taxes & fees
12 Aug - 13 Aug
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Rosé All Day: Wine Country Getaway! Walk to Dining
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and dishwasher.

Rosé All Day: Wine Country Getaway! Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (14)
"Just what we needed for a few days away! Great location with plenty of food and activities nearby! "
Rosé All Day: Wine Country Getaway! Walk to Dining
Birds and Bees Cottage
Fully equipped kitchen with oven, sink, and window.

Birds and Bees Cottage

10.0 out of 10, Exceptional, (44)
"Lovely little cottage in the country. Perfect porch for sipping coffee in the morning or watching to sunset. Close to wineries, breweries, hiking and not far from Charlottesville! We enjoyed sitting around the fire pit in the Adirondack chairs. "
Birds and Bees Cottage
Isolated cottage with good view close to many winery and Brewers.
Situated on a grassy slope, this house features a charming porch and a prominent chimney.

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is NZ$355
includes taxes & fees
28 July - 29 July
Isolated cottage with good view close to many winery and Brewers.
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Escape to a serene riverside retreat surrounded by lush greenery and a well-maintained lawn.

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

10.0 out of 10, Exceptional, (19)
"We had a great time starting here on spring break."
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Unique Cypress cottage, close to Charlottesville with mountain views.
Escape to a secluded cabin surrounded by lush forest and a sheltered porch.

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (32)
"Great cabin. Layout, furnishings and touches exceeded expectations. Organized and easy. Loved the lighting and plants. Train was a bonus. We’ll be back. "
The price is NZ$476
includes taxes & fees
20 Aug - 21 Aug
Unique Cypress cottage, close to Charlottesville with mountain views.
Quiet Blue Ridge Mountain Cottage
Enjoy a peaceful outdoor space with a comfortable chair and table, surrounded by a natural lawn.

Quiet Blue Ridge Mountain Cottage

9.6 out of 10, Exceptional, (88)
"small, quaint little cottage that accommodated our lodging needs sufficiently"
Quiet Blue Ridge Mountain Cottage
"The Sparrow" at Historic Downtown Staunton
Compact kitchen with modern design, featuring a sink, microwave, refrigerator, and oven.

"The Sparrow" at Historic Downtown Staunton

9.8 out of 10, Exceptional, (16)
"We had a relaxing time"
"The Sparrow" at Historic Downtown Staunton
Beautiful, Remodeled Cottage in the Heart of Afton
Stroll through the serene garden, surrounded by lush greenery and vibrant flowers.

Beautiful, Remodeled Cottage in the Heart of Afton

10.0 out of 10, Exceptional, (64)
"My husband and I were just looking for a quick getaway for the weekend and this was perfect!"
Beautiful, Remodeled Cottage in the Heart of Afton
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Cozy kitchen with microwave, dining area, and a framed picture.

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (48)
"Very peaceful and comfortable place to stay."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
Loveshack, a charming tiny house on a 5 acre farm
Relax in a spacious interior with a high ceiling, featuring a leather sofa and a cozy seating area.

Loveshack, a charming tiny house on a 5 acre farm

9.4 out of 10, Exceptional, (6)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm
Brand new serene luxury cottage just off the Brew Ridge Trail
Interior

Brand new serene luxury cottage just off the Brew Ridge Trail

The price is NZ$263
includes taxes & fees
5 Aug - 6 Aug
Brand new serene luxury cottage just off the Brew Ridge Trail
Charming Mountain Escape | Hot Tub & Scenic Views
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and granite countertop.

Charming Mountain Escape | Hot Tub & Scenic Views

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay! The house is conveniently located near many popular wineries. We absolutely loved the house amenities, including the hot tub and fire pits. Beds were comfortable and kitchen was well stocked with essentials."
Charming Mountain Escape | Hot Tub & Scenic Views
The Firefly Cottage
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven.

The Firefly Cottage

9.8 out of 10, Exceptional, (40)
"Firefly Cottage was a charming escape—lush greenery, diverse surroundings, and serene farm views made it unforgettable. We thoroughly enjoyed our time in this peaceful haven, filled with beauty and variety."
The Firefly Cottage
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Relax by the pool with lounge chairs and umbrellas, surrounded by a secure fence.

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (25)
"We had a great time!! The house was spotless, hot tub was great, and the fire pit was perfect! We had fun playing pool every night and seeing the animals next door during the day. Master bedroom and bathroom are amazing!!!"
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"I had an amazing experience staying here for a week. Front desk staffs are so polite and friendly. Will recommend it any day "
Nitesh 2-night trip
Posted 20 hours ago
English Inn of Charlottesville

Frequently asked questions

How much do cottages in Greenwood cost?
Cottages in Greenwood range between NZ$263 and NZ$541 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 121 cottages available in Greenwood. To help you select an ideal place, use our filter tool to search for amenities or perks you prefer.
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.