Discover Your Perfect Virginia Vacation Rental

Browse stunning Virginia vacation rentals with Pathway Properties. From cozy mountain retreats to wine country escapes, find the perfect stay in Afton, Wintergreen Resort, Shenandoah, the Northern Neck & beyond. Book direct for the best rates!

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Holly Drum 10/8/26 Holly Drum 10/8/26

Trailhead at Laurel Springs: Your Wintergreen Basecamp

9 Guests | 3 Bedrooms | 6 Beds | 3.5 Baths

Holly Drum 9/18/26 Holly Drum 9/18/26

Three Bears Hideaway: Newly Renovated Condo

6 Guests | 2 Bedrooms | 3 Beds | 2 Bathrooms

Holly Drum 8/21/26 Holly Drum 8/21/26

Squirrel Away: Walk to the Slopes

8 Guests | 3 Bedrooms | 5 Beds | 2 Baths

Holly Drum 7/10/26 Holly Drum 7/10/26

Wintergreen Highland Haven: Ski In & Ski Out

6 Guests | 3 Bedrooms | 4 Beds | 3 Baths

Holly Drum 3/26/26 Holly Drum 3/26/26

Bear Paw: Easy Walk to Wintergreen

4 guests | 2 bedrooms | 2 baths

Whitney Delaney 3/1/26 Whitney Delaney 3/1/26

Fox Paw: Walk to Slopes & Village at Wintergreen

4 Guests | 2 bedrooms | 2 beds | 2 baths

Whitney Delaney 2/11/26 Whitney Delaney 2/11/26

Sunny Bear: Private Mountain Getaway

13 guests | 4 bedrooms | 8 beds | 4 baths

Holly Drum 12/1/25 Holly Drum 12/1/25

Mountain Mama: Wintergreen Slopeside Chalet

7 guests | 3 bedrooms | 2 baths

Holly Drum 8/12/25 Holly Drum 8/12/25

Trail Magic: Ski-in/Ski-out Wintergreen Escape

12 Guests | 4 Bedrooms | 8 Beds | 4.5 Bathrooms

Holly Drum 8/12/25 Holly Drum 8/12/25

Almost Heaven: Nature Trails & Cascading Falls

7 Guests | 3 Bedrooms | 4 Beds | 3 Bathrooms

Whitney Delaney 5/11/25 Whitney Delaney 5/11/25

Wintergreen Stargazer: A Charming Condo

4 guests | 2 bedrooms | 2 beds | 2 bath

Holly Drum 3/11/19 Holly Drum 3/11/19

Adventure Awaits: A Four-Season Retreat

13 Guests | 4 Bedrooms | 8 Beds | 3 Bathrooms

Discover Your Perfect Virginia Vacation Rental

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