Vacation Rentals with Hot Tub in Wintergreen

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Filtering by: Jacuzzi or hot tub

23 vacation rentals
23

Ski-in/Ski-out Wintergreen House w/ Hot Tub!

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$190

Responds fast!
avg. 12 minutes

Price per night from

$190

17

Mountain Escape in the Spring

Virginia / Wintergreen

Wintergreen apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$110

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$110

(7) Excellent 

13

Christmas Available: Luxury Mountain House w/ Resort Membership

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“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
…see more

Price per night from

$255

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$255

(3) Very Good 

16

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

Virginia / Wintergreen

Wintergreen condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$100

Price per night from

$100

26

22 Tyro - Luxury Ski In/Out Mountain Home on Upper Tyro Slope

Virginia / Wintergreen

Wintergreen house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$500

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$500

(20) Excellent 

46

Simple Pleasures -N Ridge - Holidays Upon Us

Virginia / Wintergreen

Wintergreen apartment

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
“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
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Price per night from

$150

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$150

(4) Very Good 

15

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

Virginia / Wintergreen

Wintergreen condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$100

Price per night from

$100

(24) Very Good 

24

Cabin at Wintergreen - VA Mt. Resort Luxury Rental

Virginia / Wintergreen

Wintergreen house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
“All we needed in a cabin for a great weekend getaway.” This place was great! I took a group of young adults from my church, and they were all impressed with the house. They kept asking me, "Where did you find this place?" The cabin feels very rustic a
…see more

Price per night from

$400

Price per night from

$400

26

NEW! Wintergreen Cabin w/ Private Hot Tub - Views!

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$215

Responds fast!
avg. 9 minutes

Price per night from

$215

38

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

Virginia / Wintergreen

Wintergreen house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$225

Responds fast!
avg. 9 minutes

Price per night from

$225

(9) Excellent 

41

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

Virginia / Wintergreen

Wintergreen house

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$587

Responds fast!
avg. 33 minutes

Price per night from

$587

(25) Excellent 

17

WINTERGREEN MOUNTAIN HOUSE

Virginia / Wintergreen

Wintergreen house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$199

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$199

(6) Average 

39

wintergreen pet ski hot tub fireplace hike golf pool pets firepl

Virginia / Wintergreen

Wintergreen chalet

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$200

Price per night from

$200

(9) Excellent 

24

Top of the Resort (Discounted Rates Available)

Virginia / Wintergreen

Wintergreen house

6 14 2 nights min

  • 6 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$328

Price per night from

$328

Great rentals within 20 miles that match your search

Distance approx 11.4 km from Wintergreen

(1) Excellent 

32

Shenandoah Valley Farmhouse

Virginia / Waynesboro

Waynesboro house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 13.09 km from Wintergreen

(10) Excellent 

11

Three Sisters Log Cabin

Virginia / Montebello

Montebello house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$155

Price per night from

$155

Distance approx 12.64 km from Wintergreen

13

Rock-n-Creek Cabin mile post 27 off BR Pkwy

Virginia / Montebello

Montebello log cabin

3 11 2 nights min

  • 3 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$194

Price per night from

$194

Distance approx 16.87 km from Wintergreen

5

Osceola Mill Cabins

Virginia / Steeles Tavern

Steeles Tavern log cabin

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$150

Price per night from

$150

Distance approx 7.74 km from Wintergreen

17

Country escape in the heart of the Blue Ridge Mountains

Virginia / Afton

Afton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$135

Price per night from

$135

Distance approx 19.59 km from Wintergreen

(1) Excellent 

30

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

Virginia / Ivy

Ivy house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$353

Price per night from

$353

Distance approx 19.59 km from Wintergreen

31

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

Virginia / Ivy

Ivy house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$142

Price per night from

$142

Distance approx 10.14 km from Wintergreen

(1) Excellent 

24

Maren Estate (Mountain Estate 20 min to UVA)

Virginia / Afton

Afton house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,700

Price per night from

$1,700

Distance approx 9.82 km from Wintergreen

64

The Inn at Blue Mountain Brewery

Virginia / Afton

Afton house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$699

Price per night from

$699