Showing

PreviousNext property

$125

3 BR / 3 BA / Sleeps 7

10 Reviews

$125

Book

Simple Pleasures -N Ridge - Spring is in the Air

Wintergreen condo
3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Black Bear CafĂ©. WiFi available along with TV in each bedroom and den. Discount passes available for limited sporting activities. Walking distance to Wintergarden/ Devil's Knob Golf Course/Tennis Courts and Devil's Grill. …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Fireplace
  • Suitable for children

Details

Reviews

(10)

Simple Pleasures get away... you will...want to stay!

Left on Sep 19, 2013 for a stay in September 2013

Our gang of five stayed at SP( Simple Pleasurers) it was a pleasure,three great bedrooms three baths ,we loved it, nice location, great place. We want to stay again but you're not renting it out during Thanksgiving weekend. We went to a UVa game, not a bad drive at all. We will Definitely try to rent this place again we loved it !! I vote try this place out,... Just not when I want it. he he

PreviousNext property

$200

3 BR / 2 BA / Sleeps 6

1 Reviews

$200

Book

The Bear Dance Cabin at Wintergreen

Wintergreen cabin
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Our log cabin was built in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen. We had such a great time on our family vacation that we decided to come back and look for a lot to build on. Our cabin is located towards to very top of the …
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Dishwasher
  • Freezer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

A beautiful cabin on the top of the mountain

Left on Feb 22, 2014 for a stay in February 2014

The cabin was fantastic! It was nicely decorated and very functional. The living room/kitchen area is really spacious. The owner was courteous and helpful too.

PreviousNext property

$550

5 BR / 6 BA / Sleeps 13

2 Reviews

$550

Book

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

Wintergreen house
5 BR / 6 BA / Sleeps 13 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

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 Golf course, a big dinning room, a office, 2 large …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

This house exceeded all of expectations!

Left on Feb 23, 2015 for a stay in February 2015

Cleanliness: everything was extremely well kept and clean. There were helpful notecards lying around that let us know how to use the large variety or appliances in the house. The bathrooms were in tip top shape.

Location: the house is perfectly located about 3 minutes from the mountain. We had no issues finding the house

Rooms: the master suites were large and extremely well decorated. The…

PreviousNext property

$100

2 BR / 2 BA / Sleeps 6

5 Reviews

$100

Book

Wintergreen - Mountain Views w/ Resort Pass

Wintergreen condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Top Floor with views, Fireplace, 2 bedroom (queen, double and single), 2 sofa beds, 2 baths, 3 Flat Screen TVs, cable, DVD player, XBOX, Movies, Keurig, WiFi, VOIP, near top of advanced slope, top floor end unit, view, non-smoking Near pool and spa, short walk behind building to access slopes Membership provides …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - over five

Details

Reviews

(5)

wintergreen is a perfect spot to share views, hikes, and family memories

Left on Jun 08, 2014 for a stay in May 2014

we have been visiting wintergreen for 20 years and now have the perfect condo for our family of 6 to continue building memories. it's perfect for ski-in, ski-out vacations for the winter guests. It's also very close to the pool and hiking for summer guests. You catch the sunrise over the mountains and all the music festivals from the resort below from your balcony. there are two restaurants …

PreviousNext property

$125

2 BR / 2 BA / Sleeps 6

2 Reviews

$125

Book

Mountain Getaway

Wintergreen house
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Chalet style. High ceilings and airy feel. Walking distance to all major attractions on mountain. Minutes away by car from breweries and restaurants. Clean and comfortable. A great value for a great get away.
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Awesome Location and Great Deal

Left on Nov 24, 2014 for a stay in November 2014

Awesome rental and the owners are super nice, really enjoyed our stay. Great location, close to everything, including breweries and restaurants. Slopes were very close and had some cool places to hike too.

PreviousNext property

$135

2 BR / 2 BA / Sleeps 6

1 Reviews

$135

Book

On the Golf Course/ Member Pass to Pool/Golf

Wintergreen condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

We are full members of Wintergreen. This means as a guest of our condo you will receive a guest pass (up to 4 guests) to resort amenities that are closed to the public including the Aquatics/Fitness Center; Tennis Courts; Mountain Golf Course etc. (fees apply for these amenities). Mountaintop Condo Overlooking …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fairway Woods @Wintergreen Resort in Virginia

Left on Jun 01, 2014 for a stay in May 2014

My husband and I travel all over this beautiful country of ours and around the world. We try to stay in condos whenever possible. Thank you Copelands and Flipkey for making this condo available for rent! This was one of the nicest and most well-appointed condos we've ever enjoyed! It was extremely comfortable and so well-furnished, right down to the pillows on the comfy beds. It had absolutely …

PreviousNext property

$400

5 BR / 3 BA / Sleeps 10

16 Reviews

$400

Inquire

Cabin at Wintergreen - VA Mt. Resort Luxury Rental

Wintergreen house
5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

**** GUEST PASSES - WI-FI - FLAT SCREEN TV - HOT TUB - SCREENED IN PORCH - 2 MASTERS - RELAXATION - PEACE - & TRANQUILITY ALWAYS **** Bonnie Fagan has designed and built a fabulously luxurious 4-bedroom, 3-bath, log and stone vacation home in the Wintergreen VA Resort. The Fagan's offer this luxury vacation rental…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(16)

Gorgeous stone & log cabin - Awesome!

Left on Oct 25, 2010 for a stay in July 2010

Gorgeous Cabin in Wintergreen, Va. Spacious, relaxing, the perfect getaway. Great for hanging out with a huge fireplace - probably really cozy on those cold winter nights. Awesome golf and tennis facilities and everyone on the mountain was nice to deal with. The activity passes helped with the kids down at the lake. Also enjoyed having wi-fi access and the flat screen tv with cable just to …

PreviousNext property

$300

4 BR / 3 BA / Sleeps 10

1 Reviews

$300

Book

Mountain Ski/Golf/Tennis resort Townhouse

Wintergreen house
4 BR / 3 BA / Sleeps 10 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

A luxurious 4 season family vacation or weekend getaway in WINTERGREEN RESORT! Our mountain home includes GUEST PASSES, which allow access (fees required) to the Wintergarden Indoor Pool and Spa, two golf courses, and children's Out of Bounds recreation activities. Your passes also give you access to Lake Monocan …
    • Suitable for children

    Details

    Reviews

    (1)

    Excellent Weekend

    Left on Mar 09, 2015 for a stay in March 2015

    We had a fantastic weekend staying at this house so we could get one last weekend of skiing/snowboarding for 2015. The house nicely accommodated the our family 6 adults and 4 kids. This was the first time renting a house versus staying in a hotel in Waynesboro and the convenience was wonderful. The house was well stocked with all the needed kitchen items. We definitely will look into coming …

    PreviousNext property

    $135

    3 BR / 3 BA / Sleeps 6

    2 Reviews

    $135

    Book

    Condo on the ridge with spectacular view

    Wintergreen condo
    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Revel in this condominium atop the Blue Ridge at award-winning Wintergreen Resort, 45 minutes southwest of Charlottesville, two hours and 45 minutes from Washington. The unit is available for weekly/weekend rentals at super discount rates from the owner. You'll have most amenities of the resort at half the cost _ or …
    • Mountain Views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Washing Machine
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Loved this condo

    Left on Feb 01, 2014 for a stay in January 2014

    The condo was spacious, well stocked, visually pleasant,convenient and fun. The views were really great. Price was very reasonable. I understand that not having use of the spa helped keep the price down. That was fine because we were there to just ski. Owner was very responsive and amenities supplied as needed. Very satisfied and would stay there again.

    PreviousNext property

    $255

    3 BR / 3 BA / Sleeps 7

    5 Reviews

    $255

    Inquire

    Wintergreen Mountain 2 or 3 K Masters Resort PASSs

    Wintergreen condo
    3 BR / 3 BA / Sleeps 7 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    Come play outside on the mountain in the heart of Wintergreen Resort. You'll be right beside the Spa and the golf course. Chilly? Turn on the fireplace. Private but close to everything. PASSES cover all our guests for Aquatics and Fitness Center right next door with its beautiful indoor and outdoor pools and hot tubs…
    • Mountain Views
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children

    Details

    Reviews

    (5)

    Comfortable, good location and affordable

    Left on Jul 12, 2010 for a stay in July 2010

    The condo is spacious with (3) large bedrooms each with attached bath & comfortable beds. Kitchen is well equiped although with dated appliances; has washer & dryer. Nice walk out patio with ell kept yard overlooking golf fairway. Pleasant in evenings to sit out before dinner.

    PreviousNext property

    $195

    3 BR / 2 BA / Sleeps 8

    7 Reviews

    $195

    Book

    Mountain Chalet in Heart of Resort Sleeps 6-8

    Wintergreen house
    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 7 Reviews

    Details

    Reviews

    (7)

    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 the winter months. On warm days, linger on the …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (7)

    Cozy, Clean and Inviting!

    Left on Sep 20, 2012 for a stay in August 2012

    I stayed here for a week with my husband and 3 children. It's a lovely place!
    The proximity to the Mountain Inn and many of the main attractions is ideal--within walking distance.
    The chalet was very clean, and I have to say, the beds are so comfortable and I slept so soundly. The kids had a wide assortment of board games to choose from and we spent alot of time on the deck--it's great. I was up …

    PreviousNext property

    $143

    2 BR / 1 BA / Sleeps 4

    1 Reviews

    $143

    Book

    Private 2BR Cabin on Mountain Stream-Screen Porch

    Wintergreen cabin
    2 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    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 silverware has everything you need except the food. …
    • Waterfront
    • Ocean or water views
    • Mountain Views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Great get away for us and our dog!

    Left on May 04, 2014 for a stay in April 2014

    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!

    PreviousNext property

    $164

    3 BR / 1 BA / Sleeps 8

    3 Reviews

    $164

    Book

    Virginia Blue Ridge Mountain Cabin Rental-Foxwood

    Wintergreen house
    3 BR / 1 BA / Sleeps 8 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    You'll be delighted with this 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 on mountains trails, driving on the Blue Ridge Parkway, …
    • Mountain Views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    A Bit of heaven

    Left on Mar 08, 2010 for a stay in February 2010

    Stan, again we want to say Thank you Very Much,
    our family had a great time like usually.
    We even had a change of cabins than we normal stay at and we still had a great time. We normally come
    in the winter but we are thing maybe a weekend in the summer. We have recommended to our friends about Cabin Creekwood and the have all said "Great time"
    Andre

    PreviousNext property

    $105

    2 BR / 2 BA / Sleeps 6

    7 Reviews

    $105

    Book

    Wintergreen Resort 2 BR 2 BA Condo with LOW Rates

    Wintergreen condo
    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 7 Reviews

    Details

    Reviews

    (7)

    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, to ensure the Condo is clean, comfortable and …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (7)

    First Family Outing

    Left on Apr 08, 2013 for a stay in July 2012

    This was the first time that my wife & I were taking our son and his new bride on a family vacation. We liked the Wintergreen Resort because it would be close enough for all of us to drive home in a matter of under 4 hours. The condo was excellent with beautiful views and the pool area was outstanding. There are good places to eat while on the resort, and you are within minutes of reaching the …

    PreviousNext property

    $329

    6 BR / 5 BA / Sleeps 14

    1 Reviews

    $329

    Inquire

    Spacious 6 Bedroom Home in the Wintergreen Resort

    Wintergreen house
    6 BR / 5 BA / Sleeps 14 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    The Wintergreen Chalet is a sprawling 6-bedroom 4.5 bath home located at the top of Devil's Knob Mountain within the Wintergreen Resort in the Blue Ridge Mountains of Virginia. The home sleeps 12-14 comfortably and is available for rent daily or weekly throughout the year. Our home is set on a private road at one …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Wonderful house at Wintergreen Resort

    Left on Jan 07, 2015 for a stay in December 2014

    We spent 10 days of our Christmas Holiday in this home at Wintergreen Resort. It was a great house with plenty of room... 8 adults & 4 kids all had plenty of space. The kitchen was well equipped and the dining room fit all of us! Very clean and well furnished. Would recommend this home and hope to go back and us it again next year!

    PreviousNext property

    $125

    3 BR / 2 BA / Sleeps 7

    13 Reviews

    $125

    Inquire

    Cozy Home with Beautiful Views, Ski in/Out!

    Wintergreen house
    3 BR / 2 BA / Sleeps 7 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    **BRAND-NEW KITCHEN & UPDATED BATHROOMS** Welcome to 'Point of View'! Enjoy the beautiful year-round views from our cozy mountain home located directly on the Tyro ski slope. This is a true four-season get-away. In the winter, step out the door, put on your skis and head down the mountain. If you need a break, you …
    • Waterfront
    • Mountain Views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (13)

    A perfect place for our family!

    Left on Aug 04, 2013 for a stay in July 2013

    Our family of 5 just stayed in this warm & cozy house in a terrific location for a week! We could easily have slept many more in this home right on a ski slope in the gorgeous Blue Ridge Mountains. The house came with everything except food! Towels, sheets, cable, board games, every kitchen utensil, furniture on the deck, pool passes and the most incredible view. It was close to the lodge, the…

    PreviousNext property

    $250

    3 BR / 4 BA / Sleeps 8

    5 Reviews

    $250

    Book

    Luxury House on Mountain Golf Course w/ WPI Pass

    Wintergreen house
    3 BR / 4 BA / Sleeps 8 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    Book now for Spring/Summer vacations! Mother's Day Weekend still available. Inquire about spring discount rates. We have exclusive rights to Wintergreen Resort membership! 3500+sq ft Gorgeous/Custom Built House *** Two Master Bedroom/Bath Suites with flat screen TV's *** FREE Wi-Fi *** FREE long-distance calling …
    • Mountain Views
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Fireplace
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (5)

    Mother/Daughter Weekend

    Left on Sep 13, 2013 for a stay in August 2013

    My mother and I stayed here for a weekend away, and we had an amazing time. The house is gorgeous with a huge spacious living room for sitting and relaxing. The backyard deck is also a good place to relax with a glass of wine and a good book. The backyard backs right up to the golf course which provides a good view. The house was very neat and clean when we arrived and almost everything we could …


    Looking for more rentals?


    We're showing only results that match your dates and preferences.


    See all 58 Wintergreen rentals, all 0 Central Virginia rentals, or start a new search.


    There are no more results in Wintergreen. Top of page