30 Best Wintergreen Apartments on Holiday Lettings - Vacation rentals

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75 Vacation rentals

(2) Excellent 

15

Wintergreen ski condo to rent.

Virginia / Wintergreen

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a large group/family. Do you …see more

from $125 / night

$825 / week

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from $125 / night

(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

$1,043 / week

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Responds fast!
avg. 1 hour 58 minutes

from $149 / night

(7) Excellent 

13

Vacation home in Wintergreen

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Book now for Spring/Summer. We have been booked every weekend (Sep -Oct). Some March weekends still available. We have brand new living room furniture - so new that the pictures are not yet posted online. We have the Wintergreen Resort membership so you have access to …see more

from $265 / night

$1,400 - $1,700 / week

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Responds fast!
avg. 3 hours 13 minutes

from $265 / night

(3) Very Good 

19

Ski apartment to rent in Wintergreen

Virginia / Wintergreen

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 - $855 / week

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Responds fast!
avg. 2 hours 33 minutes

from $125 / night

(27) Excellent 

Certificate of Excellence

11

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 $105 / night

$550 / week

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Responds fast!
avg. 1 hour 36 minutes

from $105 / night

17

Wintergreen ski apartment to rent.

Virginia / Wintergreen

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • 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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Responds fast!
avg. 2 hours 28 minutes

from $110 / night

(2) Excellent 

22

Wintergreen Vacation home rental

Virginia / Wintergreen

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • 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 $180 / night

$1,260 - $2,800 / week

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avg. 8 minutes

from $180 / night

(4) Excellent 

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

$1,043 / week

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Responds fast!
avg. 1 hour 58 minutes

from $149 / night

23

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 awaits you at this 3-bedroom, 2-bath vacation rental house which sleeps 8 in Wintergreen. Located at the summit of Eagle's Swoop, this home has ski-in/out access to Wintergreen Resort's main ski slope, along with a private hot tu …see more

from $185 / night

$1,295 - $3,465 / week

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avg. 38 minutes

from $185 / 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

(15) 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

22

Wintergreen Vacation home rental

Virginia / Wintergreen

5 21 1 night min

  • 5 bedrooms
  • Sleeps 21
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Sleeps 21. Three master suites. On golf course next to ski slopes and hiking in Blue Ridge Mountains at Wintergreen Resort.Two minutes and you are on ski slopes. Free ski shuttle. Breweries, Cideries, Wineries close 20 min drive. Walk 2 Spa for a masage and indoor pool/ …see more

from $85 / night

$595 / week

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from $85 / night

(1) Excellent 

13

Ski home to rent in Wintergreen

Virginia / Wintergreen

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
This is a SUPER beautiful modern home with 5 bedrooms, 3 full bathrooms and 2 half baths. All hardwood floors except for the tile kitchen.There are 2 big family rooms perfect for big families or groups of friends. 3 big flat screen TVs and pingpong. Two large dining roo …see more

from $590 / night

$2,800 - $3,900 / week

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Responds fast!
avg. 1 hour 3 minutes

from $590 / night

22

Vacation apartment in Wintergreen

Virginia / Wintergreen

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $150 / night

$710 / week

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from $150 / night

(5) 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

$1,600 - $2,700 / week

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avg. 1 hour 3 minutes

from $310 / night

16

Ski condo to rent in Wintergreen

Virginia / Wintergreen

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY ABOVE THIS UNIT: 8743003 Do you have a large group/family. Do you need 4 Bedrooms? Do you need …see more

from $125 / night

$825 / week

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from $125 / night

39

Wintergreen Vacation home rental

Virginia / Wintergreen

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
* 15% discount for 1 week bookings * Explore all the best of Wintergreen, Virginia from this newly built 5-bedroom, 4.5-bath vacation rental home that sleeps 12. Boasting a spacious deck with views, an outdoor grill and close proximity to a wide range of indoor and out …see more

from $315 / night

$2,205 - $3,325 / week

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Responds fast!
avg. 9 minutes

from $315 / night

25

Vacation studio in Wintergreen

Virginia / Wintergreen

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Experience the best of Wintergreen from this 1-bath vacation rental studio located right in the Wintergreen Resort! Offering the best spot in the mountains, with splendid views of the ski lifts and resort activities from the private balcony, this home offers the perfect …see more

from $85 / night

$595 - $1,365 / week

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Responds fast!
avg. 8 minutes

from $85 / night

(8) 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

$2,300 - $3,200 / week

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Responds fast!
avg. 1 hour 3 minutes

from $450 / night

(9) Excellent 

41

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

$3,200 - $3,400 / week

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Responds fast!
avg. 1 hour 3 minutes

from $550 / night

(20) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $130 / night

$800 - $1,000 / week

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Responds fast!
avg. 2 hours 3 minutes

from $130 / night

(6) Very Good 

23

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 $95 / night

$750 / week

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Responds fast!
avg. 2 hours 33 minutes

from $95 / night

(16) 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 $150 / night

$1,050 / week

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Responds fast!
avg. 23 minutes

from $150 / night

24

Wintergreen Vacation home rental

Virginia / Wintergreen

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Nestled at the top of Wintergreen Mountain Resort within the Virginia wilderness, this 4-bedroom, 3-bath vacation rental house that sleeps 9 is the perfect destination for your next ski trip or relaxing getaway. With hiking trails, wineries, breweries, state parks, and …see more

from $285 / night

$1,995 - $3,115 / week

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Responds fast!
avg. 8 minutes

from $285 / night

(1) Excellent 

21

Wintergreen ski home to rent.

Virginia / Wintergreen

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 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 priv …see more

from $395 / night

$2,600 / week

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Responds fast!
avg. 1 hour 39 minutes

from $395 / night

(1) Excellent 

9

Home rental in Wintergreen

Virginia / Wintergreen

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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

$1,200 - $1,500 / week

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Responds fast!
avg. 2 hours 9 minutes

from $275 / night

(1) Excellent 

28

Vacation home in Wintergreen

Virginia / Wintergreen

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to A Cajun Chalet! We are located in the Blue Ridge Mountains, inside Wintergreen Resort. Beautiful modern home with 4 bedrooms, and 3 bathrooms, with a hot tub and a stream, and central AC and the All Access passes! The passes allow you to do the 3 things at W …see more

from $490 / night

$2,800 - $3,100 / week

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Responds fast!
avg. 1 hour 3 minutes

from $490 / night

24

Vacation home with shared pool in Wintergreen

Virginia / Wintergreen

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to the Wintergreen mountains in this custom 3-bedroom, 3.5 bathroom vacation rental home. Plush furnishings and modern amenities comfortably accommodate up to 10 guests throughout 3,500 square feet of well-appointed living space. This home is ideally situated on …see more

from $265 / night

$1,855 - $2,975 / week

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Responds fast!
avg. 8 minutes

from $265 / night

10

Ski condo to rent in Wintergreen

Virginia / Wintergreen

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ski
  • Child friendly
  • Air conditioning
Take advantage of all the Blue Ridge Mountains have to offer while staying at this CHARMING FIRST FLOOR CONDO. This premier Wintergreen vacation rental is ideally situated within a short distance of Wintergreen Resort, on the 12th hole of Devils Knob Golf Course. From t …see more

from $76 / night

$150 - $700 / week

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from $76 / night

23

Ski home to rent in Wintergreen

Virginia / Wintergreen

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Located on a wooded half acre lot on a quiet cul-de-sac, Split Rock Trail provides a feeling of privacy while offering easy access to everything the four-season Wintergreen Resort has to offer. Boasting a perfect layout for groups and families, Split Rock Trail has a fu …see more

from $300 / night

$1,875 / week

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from $300 / night