COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Wintergreen Rentals with Pools

Updating...

age 0-16
32 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

32 houses in Wintergreen with pools

Updated Wintergreen Resort Home w/ Mountain Views!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$224

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$225

July Available: Luxury Mountain House on Golf Course 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. You will love it! It is also perfect for 2-3 couples with 3 1/2 baths and 3 private bedrooms. The master suite is gorgeous!

Responds fast! avg. 3 hours 11 minutes

Match: Swimming pool

All filters match

Price per night from

$338

Wintergreen Cabin w/Private Hot Tub, Deck & Views!

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 45 minutes

Match: Swimming pool

All filters match

Price per night from

$213

2BR Walkout Condo Private and Cozy!

Wintergreen apartment

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

All filters match

Price per night from

$138

'5 Peaks' Luxury Wintergreen Resort Home w/Hot Tub

Wintergreen house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$294

Luxury Custom Home in Wintergreen Resort Area!

Wintergreen house

3 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$314

Wintergreen Resort Mountain Condo w/ Pool Access!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$107

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$166

Cozy Wintergreen Area Resort Condo - Walk to Lift!

Wintergreen condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$137

Wintergreen Resort Home w/ Deck - 5 Min to Slopes!

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$414

Mountaintop Wintergreen Resort Home w/ Deck+Views!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$225

Cozy Mountain Retreat with Radiant Floor Heat - Dog Friendly

Wintergreen house

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

All filters match

Price per night from

$144

Ski-In Ski-Out Wintergreen Condo w/Balcony

Wintergreen condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$125

Prvt Cabin w/Hot Tub, Mins to Wintergreen Rst

Wintergreen cottage

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 13 minutes

Match: Swimming pool

All filters match

Price per night from

$326

Wintergreen Resort Cabin w/Deck-Small Dogs Allowed

Wintergreen cottage

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$237

Blue Ridge Home with Mtn Views & On-Site Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$237

Lavish Wintergreen Home w/Hot Tub by Skiing!

Wintergreen house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$391

A-Frame Cabin w/Grill, Steps to Wintergreen Slopes

Wintergreen cottage

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$198

NEW! Cozy Home: Resort Access & Fire Pit!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$208

NEW! Comfy Condo in Wintergreen - Walk to Ski Hill

Wintergreen condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 6 minutes

Match: Swimming pool

All filters match

Price per night from

$172

NEW! Wintergreen Resort Cabin w/ 2 Decks & Hot Tub

Wintergreen cottage

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$249

NEW! Cozy Wintergreen Resort Condo w/ Ski Access!

Wintergreen condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$101

Wintergreen Home w/Deck - Near Skiing & Hiking!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 17 minutes

Match: Swimming pool

All filters match

Price per night from

$119

Peaceful Getaway w/ Fire Pit & Views: Ski & Hike!

Wintergreen house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$337

NEW! Pet-Friendly Condo < 2 Mi to Ski Wintergreen!

Wintergreen condo

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$107

Spacious Wintergreen Home - Half Mile to Slopes!

Wintergreen house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$283

Wintergreen Family Ski Retreat w/ Fireplace & View

Wintergreen cottage

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$296

NEW! Spacious Wintergreen Resort Home w/ Hot Tub!

Wintergreen house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 14 minutes

Match: Swimming pool

All filters match

Price per night from

$307

Great rentals within 20 miles that match your search

Lovingston Get-Away

Lovingston apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

All filters match

Price per night from

$118

The Cottage at Sunnybank B&B

Charlottesville b&b

1 bedroom / 1 bathroom / sleeps 2

“Idyllic, relaxing setting with attentive but unobtrusive hosts including Joe, the sweetest dog ever.” Location easy to find. Peaceful with beautiful pool and walking trails. Nice places to visit nearby though it was not easy to leave the cottage. Anne and Jim made sure we had everything we needed but gave us plenty of privacy. It was almost like we'd rented the entire property. Every comfort was there from our exact food preferences to comfortable accommodations and private patio. Will visit again as soon as we can.

Responds fast! avg. 1 hour 20 minutes

Travelers’ Choice award

Match: Swimming pool

All filters match

Price per night from

$193

Maren Estate (Mountain Estate 20 min to UVA)

Afton house

6 bedrooms / 7 bathrooms / sleeps 14

Match: Swimming pool

All filters match

Price per night from

$1,947

×

Also consider