Vacation Rentals with Pool in Wintergreen


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Areas near Wintergreen

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

Filtering by: Swimming pool

Great rentals within 20 miles that match your search

1 / 40

Four Seasons Annex | Beautifully Decorated, Ivy Area Central to Town & Wineries

  • 3
  • 6
  • Min stay varies

$326

Details

1 / 28

Civil War Cabin Built by Confederate Soldier in Blue Ridge Mountains

  • 1
  • 4
  • Min stay varies

$158

Details

1 / 36

On A Mountain Stream, Pet Friendly 3BR - Oakwood

  • 3
  • 8
  • Min stay varies

$178

Details

1 / 26

Private Pet-Friendly 3BR Blue Ridge Mtn Cabin - Huge Deck

  • 3
  • 8
  • Min stay varies

$228

Details

1 / 24

Maren Estate (Mountain Estate 20 min to UVA)

  • 6
  • 14
  • 3 nights min

$1687

Details

1 / 23

Pet-Friendly Secluded Mountain Cabin by Pool - Rockwood

  • 2
  • 6
  • Min stay varies

$129

Details

1 / 64

Fit for a KING ( king size beds!)

  • 5
  • 10
  • Min stay varies

$447

Details

1 / 22

Bed & Breakfast at Penmerryl Farm - Cabin A

  • 3
  • 8
  • 2 nights min

$189

Details

1 / 31

The Library Suite | Luxurious Suite Convenient to C'ville & Wineries

  • 1
  • 2
  • 2 nights min

$160

Details

1 / 22

Pet Friendly 2BR Cabin in Blue Ridge Mtns of VA

  • 2
  • 6
  • Min stay varies

$129

Details

1 / 30

Pet Friendly 2BR House in Blue Ridge Mtns, Close to Blue Ridge Parkway

  • 2
  • 6
  • Min stay varies

$150

Details

1 / 20

The Cottage at Sunnybank B&B

  • 1
  • 2
  • 2 nights min

$165

Details

1 / 21

Lovingston Get-Away

  • 2
  • 4
  • 2 nights min

$120

Details

1 / 26

Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood

  • 1
  • 4
  • Min stay varies

$130

Details

1 / 12

Wintergreen - Slope Side w/ Resort Pass

  • 2
  • 4
  • 2 nights min

$95

Details

1 / 5

Condo on the ridge with spectacular view

  • 3
  • 6
  • Min stay varies

$115

Details

1 / 24

Cozy 2BR Wintergreen Condo w/Private Balcony

  • 2
  • 6
  • Min stay varies

$166

Details

1 / 36

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

  • 5
  • 13
  • Min stay varies

$546

Details

1 / 15

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

  • 2
  • 6
  • Min stay varies

$125

Details

1 / 20

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

  • 2
  • 4
  • Min stay varies

$148

Details

1 / 19

2BR Newly Renovated Private and Cozy!

  • 2
  • 5
  • Min stay varies

$125

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 / 19

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

  • 3
  • 8
  • Min stay varies

$148

Details

1 / 13

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

  • 3
  • 8
  • Min stay varies

$255

Details

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1 / 23

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

  • 3
  • 8
  • Min stay varies

$186

Details

1 / 37

Mountaintop Resort-Center 3 Kings Twins PASSes

  • 3
  • 7
  • Min stay varies

$248

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

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