Updating...

Enter dates for more accurate prices

Wintergreen Rentals with Pools

Filter

Wintergreen Rentals with Pools

31 vacation rentals

Simple Pleasures -N Ridge - Holidays Upon Us

Wintergreen apartment

3 bedrooms / 3 bathrooms / sleeps 7

“Wonderful” The accommodations beautiful, Simple Pleasures North Ridge Holidays Upon Us, great location, good food, great skiing for grandkids [first time], son and wife. I would definitely recommend this rental to anyone; it was absolutely stocked w

Responds fast! avg. 2 hours 2 minutes

Price per night from

$130

1 / 46

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

Wintergreen log cabin

2 bedrooms / 1 bathroom / sleeps 4

“Great get away for us and our dog!” Wonderful cabin, great location! Cabin was spotless, and well appointed. Loved the gas fireplace and screened porch. Can't wait to return to Cabin Creekwood!

Responds fast! avg. 3 hours 0 minutes

Price per night from

$149

1 / 20

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 14 minutes

Price per night from

$125

1 / 19

Wintergreen - Slope Side w/ Resort Pass

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful views, clean and comfortable condo.” We loved our stay at this condo. The view from the back deck was beautiful. We enjoyed a bit of hiking, the Zip-line, nearby Monoccan lake, family time, cooking in, and eating at area restaurants. Would c

Responds fast! avg. 1 hour 50 minutes

Price per night from

$99

1 / 11

The Bear Dance Cabin at Wintergreen

Wintergreen log cabin

3 bedrooms / 2 bathrooms / sleeps 6

“Very nice accomidations, close to resort & slopes” The cabin is adorable & cozy. Even though it has a cabin feel, the bathrooms and kitchen are very nice and you don't feel like you're "roughing it" at all. The place a newer build, so it feels very cl

Responds fast! avg. 55 minutes

Price per night from

$175

1 / 20

Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

Wintergreen house

3 bedrooms / 1 bathroom / sleeps 8

“Great mountain getaway!” Conveneintly located near Wintergreen Resort, this is an awesome way to enjoy snowboarding and sking. The cabins are quaint and cozy and the owners are very nice. Especially their Jack Russell Toby! He visits every cabin eve

Responds fast! avg. 3 hours 0 minutes

Price per night from

$149

1 / 19

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

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

1 / 15

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

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$100

1 / 16

Fit for a KING ( king size beds!)

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

“Great!” 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

Responds fast! avg. 36 minutes

Price per night from

$424

1 / 68

The Mountain House

Wintergreen house

5 bedrooms / 3 bathrooms / sleeps 12

“A wonderful stay” Our family traveled to Barbara's home to enjoy a relaxing getaway and celebrate a college graduation! The house is equipped with everything you need- comfortable beds and immaculate. I would give it a 5.- and know that we will look

Responds fast! avg. 2 hours 32 minutes

Price per night from

$275

1 / 9

July 9 Week Available: Luxury Mountain House w/ Resort Membership

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 8

“Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean

Responds fast! avg. 2 hours 33 minutes

Price per night from

$275

1 / 13

A Cajun Chalet

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 36 minutes

Price per night from

$451

1 / 32

Chestnut Place Mountain Lodge

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 15

Responds fast! avg. 36 minutes

Price per night from

$549

1 / 24

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

Wintergreen house

5 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 36 minutes

Price per night from

$551

1 / 41

ALMOST HEAVEN AT WINTERGREEN RESORT!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 36 minutes

Price per night from

$389

1 / 29

wintergreen pet ski hot tub fireplace hike golf pool pets firepl

Wintergreen chalet

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 39

Cozy Custom Home in Wintergreen Resort Area!

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 35 minutes

Price per night from

$265

1 / 24
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more