Wintergreen House Rentals, Cabins & more


1 - 38 of 86

View larger map

Areas near Wintergreen

Travelers going to Wintergreen are booking December dates now. Secure your vacation rental today and have the perfect trip.

Great rentals within 20 miles that match your search

1 / 4

Cozy in Crozet

  • 2
  • 4
  • 1 night min

$184

Details

1 / 23

Pet-Friendly Secluded Mountain Cabin by Pool - Rockwood

  • 2
  • 6
  • Min stay varies

$128

Details

1 / 17

Rose Cottage at Steeles Tavern

  • 3
  • 6
  • 2 nights min

$159

Details

1 / 5

Osceola Mill Cabins

  • 1
  • 3
  • 1 night min

$149

Details

1 / 8

Spacious house located in Shenandoah Valley

  • 4
  • 6
  • 2 nights min

$90

Details

1 / 5

Condo on the ridge with spectacular view

  • 3
  • 6
  • Min stay varies

$116

Details

1 / 19

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

  • 3
  • 8
  • Min stay varies

$148

Details

1 / 12

Wintergreen Resort 2 BR 2 BA Condo with LOW Rates

  • 2
  • 6
  • 2 nights min

$105

Details

1 / 41

CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)

  • 5
  • 13
  • Min stay varies

$546

Details

1 / 24

Cozy 2BR Wintergreen Condo w/Private Balcony

  • 2
  • 6
  • Min stay varies

$165

Details

1 / 20

Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch

  • 2
  • 4
  • Min stay varies

$148

Details

1 / 11

Mountain Chalet in Heart of Resort Sleeps 6-8

  • 3
  • 8
  • Min stay varies

$196

Details

1 / 12

Wintergreen - Slope Side w/ Resort Pass

  • 2
  • 4
  • 2 nights min

$95

Details

1 / 64

Fit for a KING ( king size beds!)

  • 5
  • 10
  • Min stay varies

$447

Details

1 / 20

The Bear Dance Cabin at Wintergreen

  • 3
  • 6
  • Min stay varies

$125

Details

1 / 46

Simple Pleasures -N Ridge - Holidays Upon Us

  • 3
  • 7
  • 2 nights min

$129

Details

1 / 15

Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

  • 2
  • 6
  • Min stay varies

$125

Details

1 / 19

2BR Newly Renovated Private and Cozy!

  • 2
  • 5
  • Min stay varies

$125

Details

1 / 22

Comfortable 3BR Wintergreen House w/Wifi, Multiple Decks & Resort Shuttle

  • 3
  • 8
  • Min stay varies

$191

Details

1 / 13

Book now for Fall - Luxury House on Golf Course with Resort Membership

  • 3
  • 8
  • Min stay varies

$254

Details

1 / 16

Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC

  • 3
  • 8
  • 2 nights min

$169

Details

1 / 16
1 / 9

4 Season Mountain Inn Retreat

  • 1
  • 4
  • 2 nights min

$95

Details

1 / 7

Dogwood Haven

  • 2
  • 4
  • Min stay varies

$154

Details

1 / 23

3BR Ski-In/Out Eagle Swoop House w/Hot Tub!

  • 3
  • 8
  • Min stay varies

$184

Details

1 / 14

TREELOFT- in the snow drift!

  • 3
  • 8
  • Min stay varies

$308

Details

1 / 20

BLUE HOUSE

  • 3
  • 6
  • Min stay varies

$224

Details

1 / 26

22 Tyro Court ~ RA153723

  • 4
  • 10
  • 4 nights min

$566

Details

1 / 17

Mountain Escape in the Spring

  • 2
  • 5
  • Min stay varies

$110

Details

1 / 9

The Mountain House

  • 5
  • 10
  • 2 nights min

$273

Details

1 / 5

Wintergreen Retreat - New Luxury Post & Beam Home

  • 4
  • 12
  • 3 nights min

$298

Details

1 / 9

Open Concept Home, each BR with Walk Out Deck

  • 4
  • 9
  • 2 nights min

$199

Details

1 / 21

The Retreat at Wintergreen

  • 4
  • 10
  • 3 nights min

$392

Details

1 / 37

Mountaintop Resort-Center 3 Kings Twins PASSes

  • 3
  • 7
  • Min stay varies

$248

Details

1 / 25
1 / 17

WINTERGREEN MOUNTAIN HOUSE

  • 4
  • 8
  • Min stay varies

$200

Details

1 / 24

Spacious 6 Bedroom Home in the Wintergreen Resort

  • 6
  • 14
  • 2 nights min

$327

Details

Recent reviews for Wintergreen

"Very comfortable, all the conviences of home with a great view of the golf course ."

Left on 06/06/2017 for a stay in June 2017
Perfect condo if you need two bed rooms, very comfortable with a great view of the tee on the golf course . Great place to relax . A lot of attractions, plenty of things to do while my husband was golfing. Went to the antique shops in the area and the Berry Farm Winery. We enjoyed he cider mills and the brewing companies. Would definitely stay there again, really enjoyed staying at the condo.

"Great!"

Left on 01/17/2017 for a stay in January 2017
The process of reserving, paying, getting in the house and out of the house was easy and fool-proof!! The house was amazing and the location was perfect. Dawn (the contact for the house) was the most helpful and thoughtful person you could imagine... anything you would be able to think of you mind need- she thought of... and was available the whole stay! Amazing experience.

"Great chalet...lots to do"

Left on 07/04/2017 for a stay in June 2017
This was a fabulous resort area, lots to do and places to see however you need to pick up a map from the Mountain Inn to better get around. The chalet has everything needed for a wonderful stay and is close to wineries, Monticello, Natural Bridge, caverns, hiking trails and the Blue Ridge Parkway. Lots of wild life can be seen from the deck. Sylvie is fantastic. She replies quickly to communications and was very professional.

"Beautiful home and wonderful views"

Left on 08/07/2017 for a stay in August 2017
Very spacious home in a beautiful setting. Wonderful deck with view of golf course. So much provided by the owner [ paper towel, napkins, toilet paper, etc. ]. Enjoyed the wineries in the area. Was a great place for three couples to get together and relax.

"Great Weekend Getaway!"

Left on 09/12/2016 for a stay in September 2016
We wanted to get away for the weekend and the owner was very accommodating at last minute booking. This was our first time here and we had a great time. The house is located in Wintergreen Resort with lots of fun activities to do, such as hiking, stargazing, spending time at the lake, arts festival and music on the lawn. The house was very cozy and relaxful. We enjoyed our time cooking marshmallow at the firepit and using the outdoor grill. We recommend this place to anyone looking for a relaxful place to spend time with their family. The owner is very pleasant, responsive, and accommodating!
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more