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Roseland Holiday Vacation with Pools

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    C$274 Average
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    Don't let other travellers get your favourite Roseland area vacation rental. You're so close to securing your perfect getaway. Book today.
    26 Matching Rentals in the Roseland AreaView all 52 rentals
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    Roseland
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    The following rentals are within 25 kilometres of Roseland.
    Fit for a KING ( king size beds!)1 / 68
    (8)Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Chestnut Place Mountain Lodge1 / 24
    (2)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (20)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2017
    Condo was well stocked and very comfortable for family of five. Loved the Christmas decorations and the fireplace. Could be cleaned a little better. Especially the oven that...
    Reviewed February 27, 2017
    What a lovely little place. We stayed with our family 2 sons and their wives and 2 of my grandchildren. Very accommodating. Although it was a bad weekend for tubing and...
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    About this property
    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 Knob Golf Course/Tennis Courts...
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    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 41
    (9)Excellent
    Wintergreen
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Washer
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 2, 2017
    We had a large group of ski patrol women and this house was perfect! Dawn was great at communication and was always available via text. The location was great. The large...
    Reviewed January 9, 2017
    Booked the house for the New Year's weekend for family skiing, hiking and celebration. Mission accomplished! House was great with plenty of room. The house was well appointed...
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    About this property
    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...
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    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    On A Mountain Stream, Pet Friendly 3BR - Oakwood1 / 36
    (4)Very good
    Tyro
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, pet-friendly vacation home is full of country charm, with country-style paintings on doors and walls scattered throughout. There's plenty of room to spread out, with a large living/dining room, a sun room, a covered deck overlooking the creek, and three bedrooms. The living room...
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    Tyro, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood1 / 26
    (5)Excellent
    Tyro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This romantic one-bedroom cabin in the Blue Ridge Mountains of Virginia is a delightful setting to bring that special person in your life. The peacefulness of the stream, just outside of the cabin, is a place to relax and let the worries of life fall away. The queen-size handmade pencil poster...
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    Tyro, Virginia 22952
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch1 / 20
    (1)Excellent
    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Wintergreen, Virginia 22952
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Bear Dance Cabin at Wintergreen1 / 20
    (16)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Certificate of Excellence
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    • Cable/satellite TV
    • Children's Pool
    • Parking
    • Washer
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 7, 2018
    We had a great stay recently at Bear Dance Cabin at Wintergreen. The cabin has a wonderful fire place which is great after a day of skiing. The location is very convenient to...
    Reviewed December 30, 2017
    Thank you for sharing your beautiful cozy cabin with us! We had a delightful Christmas getaway! The cabin has everything we needed for our fun quality family time. Convenient...
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    About this property
    Our cabin is located near the very top, elev 3515ft, of Wintergreen mountain and is on the resort property; approximately 1.5 miles from the slopes. Wintergreen is an excellent place to vacation given the warmth of the people in this part of the eclectic Blue Ridge Mountains of Virginia and the...
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    Location Information
    Wintergreen, Virginia 22958
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    July 9 Week Available: Luxury Mountain House w/ Resort Membership1 / 13
    (7)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2017
    My wife and I are from Michigan and were looking for a central location to get together with our son, daughter-in-law, daughter, and 2 year old grandson who all live in...
    Reviewed June 25, 2014
    I recently rented this home for a bachelorette weekend for a friend who is more the outdoors type then the Vegas type. It was close to our home in Northern Virginia ~3 hours...
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    About this property
    Week of July 9th still available. Aug 3-5 weekend available. New living room furniture - not shown in these pictures. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to the public! 3500+sq ft Gorgeous/Custom Built House *** Two Master...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    A Cajun Chalet1 / 31
    (1)Excellent
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 8, 2018
    What a great (long) weekend we had at the Cajun Chalet ! Dawn has everything you’ll need to cook at home after a day exploring the mountain.The secluded master bedroom upstairs...
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    About this property
    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 Wintergreen that are Private....
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wintergreen -  Slope Side  w/ Resort Pass1 / 11
    (29)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Certificate of Excellence
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We stayed in Wintergreen for a few days in August. The resort is really quiet at that time. If you are avoiding crowds it’s a good place to go in the summer. The view from the...
    Reviewed July 28, 2018
    This unit had a great location and the views were excellent. Centrally located close to the Spa and restaurants as well. Plenty of parking. The unit itself was comfortable and...
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    About this property
    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 resort with a small fee. These...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 15
    (4)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Shared Indoor Pool
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The condo was very accommodating, but we went without hot water the whole weekend. The owner forgot to tell us that the hot water was off and needed to be turned on...
    Reviewed January 17, 2018
    It was an unbelievable location. The kitchen was great, beds were comfortable, and the view was beautiful.
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    About this property
    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 need 4 Bedrooms? Do you need...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (4)Excellent
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 on mountains trails, driving...
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    Location Information
    Wintergreen, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 16
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Shared Indoor Pool
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    Condo was nice. Have no complaints. Good many stairs to the unit. Would have like to known . Good unit for the price.
    Reviewed July 25, 2018
    Easy access to trails, golf and tennis. Devils Knob first tee and just around the corner as well as the tennis facility offering clay courts and great instruction. Easy to...
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    About this property
    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 some space during your...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2BR Walkout Condo Private and Cozy!1 / 19
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 28, 2017
    The owner of this condo obviously cares a great deal about every detail and wanted to make sure our stay was an enjoyable one. The condo is immaculately clean, the beds are...
    Reviewed March 9, 2016
    We loved staying here. Most everything we needed was supplied--even coffee and basic toiletries! The bedrooms were very nice. Full washer and dryer. We plan to stay here...
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    About this property
    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 the Nature Foundation are...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Central Wintergreen Home w/ Free Resort Amenities!1 / 39
    (1)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    This house is beautiful and perfect as a family getaway. It is quiet and peaceful. We never left the house or the mountain! Although you can do both very easily. The rooms...
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    About this property
    * 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 outdoor activities, this...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Mountaintop Resort-Center 3 Kings Twins PASSes1 / 37
    (7)Very good
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 12, 2018
    Great condo located on Wintergreen mountain convenient to everything. Three bedroom all with comfortable king size beds and each has its own full bathroom. Lots of pillows...
    Reviewed December 10, 2015
    I stayed at this condo with my husband, daughter, and friends for a wedding. The location is great and near different attractions. The condo was clean and the owners had labels...
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    About this property
    Come play on the mountain! The best location In the heart of Wintergreen Resort. Private but close to everything. 2 minutes to the slopes! You'll be right beside the pool, spa and the mountaintop golf course. All Resort PASSES cover all our guests for Aquatics and Fitness Center right next door...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    wintergreen pet ski hot tub fireplace hike golf pool pets firepl1 / 39
    (6)Average
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home on one acre in wintergreen ski resort 5 - 10min walk to ski slopes, mountain inn restaurants ice rink basketball court ourdoor grill gift and ski equip shops rental and ticket office, market store deli beer wine pizza sundries, hiking , overlooks, newyears and july fourth fireworks Pets...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Mountain House1 / 9
    (1)Excellent
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, located on our near our...
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    Location Information
    Wintergreen, Virginia 23831
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 tub surrounded by towering...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    NEW! 4BR+Loft Roseland House - Deck w/ Mtn Views!1 / 24
    (1)Average
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Sauna
    • Cable/satellite TV
    • Patio
    • Washer
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    The house itself was a nice place, it was definitely a little dirty with dead bugs and cobwebs, but in general was how the listing showed. However, the management of this house...
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    About this property
    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 world-class ski slopes within...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags for an exciting Wintergreen Resort escape and stay at 'Monster Mountain Retreat!' Nestled amid the flourishing forests of the Blue Ridge Mountains, this 6-person property offers 2 bedrooms, 2 bathrooms, and access to a seasonal community pool. Whether you're skiing down the slopes...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lovingston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Parking
    • Air Conditioning
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the Village of Lovingston, VA. There are wineries, breweries, and distilleries. We have Wintergreen Ski Resort. The Lockn' Festival each August. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby we have UVa's...
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    Location Information
    Lovingston, Virginia 22949
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the Virginia mountainside in...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Wintergreen Resort from this 2-bed, 2-bath Nellysford townhome, nestled in the Laurelwood complex! Featuring all of the comforts of home, this cozy abode takes up to 5 guests on a trip of a lifetime through the Blue Ridge Mountains - where skiing, hiking, swimming, golfing...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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