25 Best Wintergreen Apartments on Holiday Lettings - Vacation rentals

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26 Vacation rentals

(1) Excellent 

20

Wintergreen Vacation log cabin rental

Virginia / Wintergreen

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Right on a mountain stream, this two-bedroom cabin is very private. No other cabins or homes can be seen. Two double beds make this very accommodating for four. The full kitchen with stove, refrigerator, microwave, coffeemaker, toaster, dishes, pots & pans, and silve …see more

from $149 / night

$1043 / week

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Responds fast!
avg. 1 hour 28 minutes

from $149 / night

(20) Excellent 

Certificate of Excellence

12

Ski condo to rent in Wintergreen

Virginia / Wintergreen

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Welcome to Wintergreen! This condo is located near the top of the Highlands lift, within walking distance to the slopes and the nearby fitness and spa center. The included membership guest passes allow access to the fitness center, spa, golf, and tennis areas of the res …see more

Certificate of Excellence

from $96 / night

$550 - $1000 / week

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from $96 / night

(3) Very Good 

19

Wintergreen Vacation home rental

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
You'll be delighted with our Pet-Friendly, fully furnished mountain home, located just two miles from the Blue Ridge Parkway, and one mile from Sherando Lake. With all the comforts of home, you'll be able to enjoy the outdoors without roughing it! Spend the day hiking …see more

from $149 / night

$1043 / week

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Responds fast!
avg. 1 hour 28 minutes

from $149 / night

(7) Excellent 

64

Vacation home in Wintergreen

Virginia / Wintergreen

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Now HERE is a really great house! Fit for a KING or two. This house has 4 large bedrooms with 2 of them having KING size beds. Then there is a Queen & 2 twins and then the loft has a twin day bed that has a pop up trundle so this could be another KING (that makes 3) ..o …see more

from $450 / night

$2300 - $3200 / week

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Responds fast!
avg. 48 minutes

from $450 / night

(9) Very Good 

11

Vacation home in Wintergreen

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Nestled in the heart of Wintergreen, a year round resort, this cozy chalet home is a brief walk to the Mountain Inn, ski slopes, restaurants, shops, and market. The house is conveniently located on a private, wooded lot and offers a view of the mountain ranges during th …see more

from $195 / night

$875 / week

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avg. 1 hour 47 minutes

from $195 / night

(14) Excellent 

12

Vacation apartment in Wintergreen

Virginia / Wintergreen

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Cozy and Convenient! Our Condo is centrally located for easy walking access to the full-service SPA, Golf course and indoor-outdoor Tennis facilities. We have been owners of this Condo for the past 9 years and love the Wintergreen Resort. We manage the Condo ourselves …see more

from $105 / night

$550 / week

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from $105 / night

(1) Excellent 

24

Wintergreen Vacation apartment rental

Virginia / Wintergreen

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Have a truly special stay at this extraordinary 2-bedroom, 2-bathroom condo with room to comfortably accommodate 6 guests. Once you witness the serene sunset vistas overlooking the valley and mountain, you will never want to leave! Upon arrival, you’ll find that the ad …see more

from $165 / night

$990 - $1050 / week

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Responds fast!
avg. 11 minutes

from $165 / night

(9) Excellent 

36

Vacation home in Wintergreen

Virginia / Wintergreen

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a really amazing home! It is so perfect for all kinds of groups because it has 3 SERIOUS master suites. You could say it is perfect for "separate togetherness". The main floor has the kitchen that overlooks a huge deck right on the 16th tee box of Devils Knob Go …see more

from $550 / night

$3200 - $3900 / week

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Responds fast!
avg. 48 minutes

from $550 / night

(18) Excellent 

46

Wintergreen ski apartment to rent.

Virginia / Wintergreen

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ski
North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Devils Knob Golf/Tennis. WiFi available along with TV in each bedroom and den. Discount passes available for limited sporting activities. Walking distance to Wintergarden/ Devil's K …see more

from $130 / night

$700 - $945 / week

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Responds fast!
avg. 2 hours 52 minutes

from $130 / night

15

Wintergreen ski condo to rent.

Virginia / Wintergreen

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Gorgeous Views/Beautiful Weather/Perfect Sectional Couch to relax!Golf/Pool Pass Please be advised we request a two night stay on the weekends, during the winter season. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a …see more

from $135 / night

$750 - $1050 / week

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from $135 / night

(9) Excellent 

Certificate of Excellence

20

Vacation log cabin rental

Virginia / Wintergreen

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
We decided to build our cabin after a family trip to WTG. We fell in love with the Wintergreen community and much like you we searched for a place to stay at Wintergreen. For us and our guests Wintergreen is a perfect getaway. Our cabin is located near the very top of …see more

Certificate of Excellence

from $125 / night

$875 / week

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Responds fast!
avg. 47 minutes

from $125 / night

(3) Very Good 

19

Ski apartment to rent in Wintergreen

Virginia / Wintergreen

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
We invite you to stay in our lovely totally updated golf-front walk-out condo, right in the heart of the Devils Knob area of Wintergreen Resort. Relax in the private, cozy cottage feel of our condo while having easy access to resort amenities. The Wintergarden Spa and …see more

from $125 / night

$750 - $1040 / week

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Responds fast!
avg. 2 hours 1 minutes

from $125 / night

(4) Excellent 

9

Vacation condo in Wintergreen

Virginia / Wintergreen

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Nestled in the Blue Ridge Mountains in the heart of Mountain Village, this loft condo has everything needed for a quick weekend getaway or an extended vacation. This unit is at the Mountain Inn, the heart of the Winter Village, and is the best condo for skiing at the re …see more

from $96 / night

$750 / week

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Responds fast!
avg. 2 hours 23 minutes

from $96 / night

22

Wintergreen Vacation home rental

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
For your next mountain getaway, why not stay somewhere that lets you truly take advantage of all the Blue Ridge Mountains have to offer? This premier Wintergreen vacation rental house does just that - ideally situated within walking distance of Wintergreen Resort, this …see more

from $191 / night

$1330 - $2800 / week

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Responds fast!
avg. 32 minutes

from $191 / night

7

Vacation apartment in Wintergreen

Virginia / Wintergreen

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
We have a newly remodeled basement with its own door and private deck. We are .6 miles from the mountain inn/ski slopes. I have a pass for the chestnut / Rodes farm pools and tennis access . We are within a half hour of several winery's and brewery's. Wintergreen is a …see more

from $155 / night

$711 - $900 / week

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from $155 / night

16

Ski condo to rent in Wintergreen

Virginia / Wintergreen

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Relax, Golf, Beautiful Views, Passes for Golf, Tennis and Pool Please be advised we request a two night stay on the weekends, during the winter season. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY ABOVE THIS UNIT: 8743003 Do you have a large group/family. Do you nee …see more

from $135 / night

$750 - $1050 / week

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from $135 / night

(1) Excellent 

9

Home rental in Wintergreen

Virginia / Wintergreen

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly
Beautiful 5 bedroom, 2 1/2 bath home located in the Blue Ridge Mountains at Wintergreen Resort, Va.We are a four season community, with golf, tennis, swimming, boating, hiking (Appalachian Trail), skiing, ice skating, tubing, horseback riding, wine tasting, and more, lo …see more

from $275 / night

$1000 / week

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Responds fast!
avg. 1 hour 57 minutes

from $275 / night

(3) Very Good 

16

Vacation home in Wintergreen

Virginia / Wintergreen

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
A skier's delight can be found at our Wintergreen vacation home on Squirrel Tree Lane, featuring ski in and ski out on the intermediate slope Tyro so that no time is wasted in traffic. Home is located 70' from the parking area, located in a private wooded area directly …see more

from $170 / night

$900 / week

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from $170 / night

5

Vacation home with shared pool in Wintergreen

Virginia / Wintergreen

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Wintergreen Retreat is a vacation rental home within the Wintergreen Resort in Virginia, set among the beautiful Blue Ridge Mountains. This brand new charming mountain getaway is nestled on Wintergreen Mountain, just a few hundred yards from gorgeous scenic overlook …see more

from $300 / night

$2100 / week

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from $300 / night

17

Wintergreen ski apartment to rent.

Virginia / Wintergreen

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Terrace level apartment of personal mtn house w/ private entrance, shared hot tub on deck, 2 bdrms, full kth, stocked wine frig, Keurig w/ coffee, LR w/ vintage Pacmac game, private W/D. Deck w/ shared hot tub. Walk to lodge/restaurants & slopes. Seasonal mountain views …see more

from $110 / night

$770 / week

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from $110 / night

(1) Excellent 

14

Vacation home in Wintergreen

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
TREELOFT #1 is Located in a really GREAT spot, right in the Middle of Wintergreen Resort. It is walking distance to several overlooks, and the main lodge called the Mountain INN, and our Market. It is just 100 STEPS to the Tyro ski slope! 200 steps from there to the top …see more

from $310 / night

$1600 - $2500 / week

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Responds fast!
avg. 48 minutes

from $310 / night

31

Vacation home with shared pool in Wintergreen

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The ultimate Blue Ridge Mountain getaway in Wintergreen, Virginia awaits you at this 3-bedroom, 2-bathroom house. Located at the summit of Eagle’s Swoop, this spectacular home has ski-in/ski-out access to one of Wintergreen Resort’s main ski slopes. Whether you’re seeki …see more

from $185 / night

$1295 - $3465 / week

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Responds fast!
avg. 3 hours 12 minutes

from $185 / night

9

Vacation home in Wintergreen

Virginia / Wintergreen

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Private garden
Welcome to our mountain home at Wintergreen Resort! We fell in love with this house for the same reasons that we know you’ll love it. There’s plenty of sleeping space with 4 bedrooms, each with its own sliding glass door that opens onto a deck. There are three decks on …see more

from $200 / night

$900 / week

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from $200 / night

26

Wintergreen Vacation home rental

Virginia / Wintergreen

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Suitable for children age 5+
  • Air conditioning
True SKI-IN/OUT 4BR newly-renovated decorated private home is located directly on the Upper Tyro slope at Wintergreen. Seriously, you can step out of the house and into your skis. In summer, the slopes offer access to many activities such as mountain-biking, the Spartan …see more

from $570 / night

$3990 - $7945 / week

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Responds fast!
avg. 2 hours 15 minutes

from $570 / night

(1) Excellent 

21

Wintergreen ski home to rent.

Virginia / Wintergreen

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ski
  • Child friendly
  • Private garden
The Wintergreen Retreat Is a spacious house with an open floor plan, four large bedrooms and four full bathrooms. Two bedrooms have king beds, one has a queen bed and another has two twins and a bunk bed. We also have two Pack and Plays. The two king bedrooms have priva …see more

from $395 / night

$2600 / week

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Responds fast!
avg. 1 hour 58 minutes

from $395 / night

5

Vacation home in Wintergreen

Virginia / Wintergreen

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Blue Chalet is a quaint little cabin in the blue ridge mountains. It has a full kitchen ,a comfortable living room that has 2 couches , 3 bedroom. There is a ping pong table down stairs , and a wii game for you to enjoy. We offer guest passes for golf , tennis & pools . …see more

from $225 / night

$1000 - $1800 / week

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from $225 / night