Wintergreen Cottages from CA $237

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Our top choices for Wintergreen cottages

A deck with a fire pit, wooden chairs, and a view of the forest.

1. Mountain Mindset: Pup Friendly + Trail

Laurel Ridge

Caine C.

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.

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

Afton

Caitlin S.

CA $237 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with wicker furniture, a brick wall, and a view of greenery.

3. Bluebird Cottage

Roseland

CA $412 total

includes taxes & fees

Oct 28 - Oct 29

A covered porch with two wooden chairs and a table, large windows, and a string of lights.

4. Modern Nellysford Getaway on 40 Private Acres!

Nellysford

CA $913 total

includes taxes & fees

Nov 4 - Nov 5

A wooden deck with a round table and chairs, a grill, and a trash can.

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

Afton

Liz D.

CA $474 total

includes taxes & fees

Nov 4 - Nov 5

6. Bluebird Cottage: Near 151 + Appalachian Trail

Roseland

Art B.

CA $472 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with a table and chairs, a railing, and a house with two windows.

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

Afton

CA $480 total

includes taxes & fees

Nov 16 - Nov 17

A stone wall, a small stream, and a house with a red roof.

8. Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls

Tyro

Nicole B.

CA $481 total

includes taxes & fees

Oct 25 - Oct 26

A single-story house with a front porch, a pathway leading to the door, and a small garden with various plants and flowers.

9. The Cottage @ Afton Mountain- Close to Wineries!

Afton

Mary R.

CA $446 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a wooden deck and a stone border.

10. Little Haven Cottage: Walk to Meade Tasting

Afton

"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...

Anonymous traveller

CA $721 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a porch, a front door, and a mailbox.

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

Charlottesville

Ron C.

CA $312 total

includes taxes & fees

Oct 27 - Oct 28

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

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

Crozet

karen r.

CA $476 total

includes taxes & fees

Nov 22 - Nov 23

A house surrounded by trees with a clear sky.

13. Artisan's Cottage

Afton

CA $419 total

includes taxes & fees

Nov 17 - Nov 18

A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

14. Unique Cypress cottage, close to Charlottesville with mountain views.

Charlottesville

David F.

CA $413 total

includes taxes & fees

Nov 16 - Nov 17

A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

15. Petite Pink Cottage, Perfect for Solo Travelers

Charlottesville

Beth V.

CA $612 total

includes taxes & fees

Oct 26 - Oct 27

A two-story house with a large lawn, surrounded by mature trees and a white picket fence.

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

Staunton

Pam W.

CA $353 total

includes taxes & fees

Oct 28 - Oct 29

A two-story white house with a front porch, a staircase, and a small front yard.

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

Charlottesville

CA $583 total

includes taxes & fees

Nov 16 - Nov 17

A deck with wooden chairs and tables, overlooking a grassy field and distant mountains.

18. Cottage on Working Turkey and Bee Farm in the Heart of Crozet

Crozet

Thomas G.

CA $636 total

includes taxes & fees

Oct 30 - Oct 31

A house with a covered porch, a door, and a garden area with plants and a hose.

19. 40 Acre - Mechum Hill Guest Cottage

Charlottesville

CA $740 total

includes taxes & fees

Oct 25 - Oct 26

20. Charming Cottage Near Vineyards

Charlottesville

Nicole M.

CA $757 total

includes taxes & fees

Nov 4 - Nov 5

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Top Wintergreen Hotel Reviews

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

10/10 Excellent

"We had a lovely experience staying at this property. We stayed two nights with our 3 kids (ages 5, 7, 9) and we all thoroughly enjoyed the hot tub, Pac Mac console and enjoyed making a fire and roasting s'mores. The house was very clean, beds were comfortable and communication was prompt. We did the Shamokin Falls and Plunge hikes which were very convenient for our young kids. The space was perfect for our needs (we were close to the resort but still felt like we got away and had privacy) - thank you!"

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent

"We were so fortunate to find this spectacular gem! The breathtaking views that pictures just cannot do justice for were amazing! The unit was so well stocked with all the essentials and one of the cleanest places we have stayed. Check-in and check-out were clear and simple. We can’t wait to book again. Thank you for sharing your piece of mountain with us. We loved it."

Family Retreat - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"The house was perfect. Kevin and Jen were VERY responsive to questions. I was unable to take the trash down to the dumpster and Kevin was super accommodating and offered a quick solution. We would absolutely stay there again. Highly recommended."

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

10/10 Excellent

"Great unit. Clean and well supplied with everything you need if you plan to prepare meals. Communication with host (Rebecca) was excellent. If you are planning to eat out and don't want to drive a long distance down the mountain and outside the Wintergreen resort, options are limited. On the resort there are 2 pizza places (which we did not try), plus The Edge (we ate there twice and it was fine), plus Devil's Knob Grill (appears to be the nicest place) but it has a restrictive member/guest policy and staying in a VRBO does not qualify."

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

10/10 Excellent

"What a lovely slopeside condo! Our family had a wonderful stay. The double bunk beds were perfect for our kids. And we loved watching the beautiful sunrise over the mountains. Everything was very clean and comfortable. Thank you for hosting us!"

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews	331
Accommodation	32 Cottages
Lowest Price	CA $237
Highest Price	CA $913

Frequently asked questions

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What is there to do in Wintergreen near my cottage?

Once you've checked in to your hotel, venture out and discover the fantastic things Wintergreen has to offer. Wintergreen Resort is a top attraction to add to your travel itinerary.

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Search Wintergreen Cottage Rentals from CA $237

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wintergreen cottages

1. Mountain Mindset: Pup Friendly + Trail

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

3. Bluebird Cottage

4. Modern Nellysford Getaway on 40 Private Acres!

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

6. Bluebird Cottage: Near 151 + Appalachian Trail

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

8. Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls

9. The Cottage @ Afton Mountain- Close to Wineries!

10. Little Haven Cottage: Walk to Meade Tasting

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

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

13. Artisan's Cottage

14. Unique Cypress cottage, close to Charlottesville with mountain views.

15. Petite Pink Cottage, Perfect for Solo Travelers

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

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

18. Cottage on Working Turkey and Bee Farm in the Heart of Crozet

19. 40 Acre - Mechum Hill Guest Cottage

20. Charming Cottage Near Vineyards

Find vacation rentals that suit your style

Top Wintergreen Hotel Reviews

Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

Find out more about Wintergreen

Wintergreen Cottages information

Frequently asked questions

Explore a world of travel with Expedia