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Wintergreen House Rentals

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    Travellers to Wintergreen are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    21 Matching Rentals in WintergreenView all 36 rentals
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    Columbus Day Weekend-  Luxury House on Golf Course with Resort Membership1 / 13
    (7)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Fit for a KING ( king size beds!)1 / 64
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 41
    (9)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (3)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • 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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    Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC1 / 16
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2017
    Beautiful setting, lovely house with toasty fireplace! Could not have been better! When we come back to Wintergreen, this will be our first choice to stay1
    Reviewed 17 September 2015
    A group of eight friends stayed at this home in the Wintergreen Resort to enjoy a wine tasting weekend. Eric was extremely helpful in the booking process, and his instructions...
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    About this property
    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 on the Tyro slope. The house...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mountain Chalet in Heart of Resort Sleeps 6-81 / 11
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2017
    We had an opportunity to stay here for 4 days and it was an exciting one. We thoroughly enjoyed each and every minute. My little girl enjoyed the stay and nearby play area. I...
    Reviewed 15 October 2014
    We stayed there with our friends. The location is perfect, just a walking distance to all attractions. The house was comfy with good size rooms.
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    About this property
    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...
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    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Spacious 6 Bedroom Home in the Wintergreen Resort1 / 24
    (7)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Grill
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2015
    This house is absolutely beautiful!! It had plenty of room for all of us, including the 8 kids. There were even games for them to play with. We had plenty of room in the kitchen...
    Reviewed 15 June 2015
    There were few things that we could not get to work. I left a list of thiings on the counter for you to look over, just some minor things that didn't work. Could have had...
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    About this property
    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...
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    Location Information
    Wintergreen, Virginia 24477
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    TREELOFT- in the snow drift!1 / 14
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Patio
    • Balcony
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2017
    We love this are to stay on the wintergreen resort. You have quick access to blue and black slopes. Great trails in the area, quick drive or short walk to all main area for food...
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    About this property
    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 of Eagles swoop and Big...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Satellite TV
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 room tables. Beautiful kitchen....
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 . Come enjoy all wintergreen...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Hot Tub
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 BR, 2.5 Bath, 2 Family Rooms, All Access Member Passes, Minutes to Everything Whether you’re looking to get outside and play or just a little R&R, Wintergreen has everything you need and is set in the perfect location…the bright, colorful and peaceful Blue Ridge Mountains!! This split-level...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    WINTERGREEN MOUNTAIN HOUSE1 / 17
    (21)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Sauna
    • Mountain Views
    • Housekeeping Included
    • Internet Access
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Time to start thinking about Fall! Stay 2 nights for $250/ night or save and stay 3 nights for $600. The leaves will be turning soon! Just Renovated, beautiful rental in the woods!!! New carpet/hardwood floors/tile bathrooms. New granite in kitchen, all new appliances, completely painted...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Satellite TV
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 home will let you enjoy easy...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Games, hiking, fishing,...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 21 Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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/ hot tub /gym. Bask at the...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 21
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    The Retreat at Wintergreen1 / 21
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Mountain Views
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2016
    Our stay at The Retreat at Wintergreen was a perfect mountain getaway! The home is very spacious, inviting and comfortable. The well stocked kitchen which is open to the...
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    About this property
    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 private bathrooms. The main level...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 overlooks – and the perfect retreat...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the house, so plenty to...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    The Mountain House1 / 9
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • 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 10
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    Cabin at Wintergreen - VA Mt. Resort Luxury Rental1 / 24
    (22)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Internet Access
    • DVD Player
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    Spent a week at this unique cabin. Had a great time! Owner was very responsive and helpful. The hot tub needed chemicals. That was corrected. The cover was very heavy and...
    Reviewed 20 February 2017
    We spent a wonderful long weekend at the cabin at Wintergreen. It is in a beautiful location overlooking the mountains and the old Appalachian Trail. The sunset from the hot...
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    About this property
    **** 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...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 seeking outdoor excitement, wine...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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