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Holiday Rentals with Pools in Montebello, VA

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    The following rentals are within 25 kilometers of Montebello, Virginia.

    1 / 12
    5 of 5 bubbles (18) Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 48
    5 of 5 bubbles (7) Excellent
    Wintergreen
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    1 / 26
    5 of 5 bubbles (5) Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 27
    5 of 5 bubbles (6) Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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) ..or they can separate into... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 25 October 2016
    My family (and extended family) stayed during the peak leafing weekend of the year. The house was incredible and suited our needs perfectly. The host was extremely helpful, not...
    5 of 5 bubbles Reviewed 11 October 2016
    We had 8 adults getting together for a long weekend of visiting many Wineries, Cidery's and Breweries just outside of Charlottesville. this is an ideal central location and Dawn...
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    1 / 29
    4.5 of 5 bubbles (7) Very good
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    We built our log cabin in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen and after such a great experieince we decided to come back and look for a lot to build on. For us Wintergreen was perfect for a young family living... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 3 November 2016
    The cabin was a pleasantly rustic in design, but very clean and modern in construction. The location was convenient for exploring the surrounding mountains, and the rental process...
    5 of 5 bubbles Reviewed 21 August 2016
    Our family of three humans and one dog, thoroughly enjoyed our time at the cabin. It was clean, spacious, comfortable, and located in a quiet residential neighborhood. The...
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    1 / 24
    Wintergreen
    7 Bedrooms, 7 Bathrooms, Sleeps 17 | Quick View
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    • Mountain Views
    • Skiing: Property Is...
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    New Listing! Mountain, Forest Views, Awesome, Spacious throughout and Spacious bedrooms, Comfortable, 3 floors, Beautiful Home and Beautifully furnished Home at Wintergreen Resort, 7 bedrooms, 6 bedrooms have a private bath. Floor to ceiling windows. Great place for Families traveling together,... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 23
    4.5 of 5 bubbles (4) Very good
    Tyro
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Grill
    • Washer
    • Porch
    • DVD Player
    • Shared Outdoor Pool...
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful 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 boasts a large... View all property information
    Location Information
    Tyro, Virginia 22952
    1 / 46
    5 of 5 bubbles (16) Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Skiing: Property Is...
    • Satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 29 October 2016
    Thank you for sharing your wonderful property with us. Our group was so delighted by your place that we wanted to keep it for ourselves! The location was perfect. We felt there...
    5 of 5 bubbles Reviewed 27 July 2016
    Condo unit was clean and well stocked with towels, bedding, and kitchen items. We did not plan on cooking in the condo, but kitchen was well stocked with items you would need if...
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    1 / 10
    5 of 5 bubbles (5) Excellent
    Tyro
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool...
    • Mountain Views
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Tyro, Virginia 22952
    1 / 5
    5 of 5 bubbles (3) Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 8 December 2014
    very nice accomidations. We had plenty to do around us and enjoyed our time there. Condo was nicely furnished.
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    1 / 6
    5 of 5 bubbles (1) Excellent
    Greenville
    Private Room, 10 Bathrooms, Sleeps 30 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Mountain Views
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Charming country retreat in the heart of Virginia Horse country. Lodge style Bed and Breakfast that also has 2 cabins all surrounding a large outdoor pool on a working equestrian center. Beautiful lake, trails, hot tub, game room, delicious breakfast and much more! Family and pet friendly. Perfect... View all property information
    Location Information
    Greenville, Virginia 24440
    5 of 5 bubbles Reviewed 24 October 2015
    We came to Pennmerryl Farm to bicycle at a fall festival held in Staunton. We drove back and forth to Staunton each day which took a good half hour. We are all animal lovers (one...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool...
    • Waterfront
    • Washer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 24
    5 of 5 bubbles (1) Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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 adjacent free off-street... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 14 September 2016
    This condo is the perfect size for a couple or small family. It is really comfortable with warm, overstuffed couches, large TVs, a gaming system and internet. The accents are...
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    1 / 10
    4.5 of 5 bubbles (3) Very good
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 14
    4.5 of 5 bubbles (27) Very good
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    **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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 3 weeks ago
    Great place to stay! Beautiful home with spectacular mountain views! Everything you need for an enjoyable getaway! Close to many wineries and breweries, too! Can't wait to come...
    3 of 5 bubbles Reviewed 11 October 2016
    I chose "Point of View" for the view. The house has a slope side view lovely in any season. Our family fit perfectly in the house and had great fun reconnecting with the fine...
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    1 / 6
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Skiing: Property Is...
    • Patio
    • Ocean Views
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ski Slope Access across the street - Mountain Cabin/Chalet - Pet Friendly - Nature awaits you A beautiful Guest Cabin/Chalet/ or call it a peaceful home with windows all around so you can look out and see mountains, hills, forest, trees, wildlife and all that nature has to offer. She is a... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 37
    5 of 5 bubbles (6) Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is...
    • Hot Tub
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Come play on the mountain! The best location In the heart of Wintergreen Resort. Private but close to everything. 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 with its beautiful indoor... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 bubbles Reviewed 10 December 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 on...
    5 of 5 bubbles Reviewed 24 June 2014
    Our family of 6 plus a small child had a fun, relaxing week at this condo. The owner was very helpful and responsive during the planning period. We found the condo to be...
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    1 / 9
    Greenville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Parking
    • Shared Garden
    • Shared Outdoor Pool...
    • Mountain Views
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Lovely & Cozy log cabin at charming country retreat at a working farm and equestrian center. Cabins are fully furnished and fully stocked with linens,towels, pots, pans, dishes and more. The facility has a full equestrian center, a lake for fishing and canoeing, lots of trails for walking or... View all property information
    Location Information
    Greenville, Virginia 24440
    1 / 5
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    1 / 19
    4 of 5 bubbles (1) Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • DVD Player
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • Mountain Views
    • Skiing: Property Is...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    We invite you to stay in our newly renovated golf-front 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 access to the shuttle just outside the door. The Wintergarden Spa and the Nature Foundation are just... View all property information
    Location Information
    Wintergreen, Virginia 22967
    4 of 5 bubbles Reviewed 9 March 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 again...
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    1 / 13
    5 of 5 bubbles (5) Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Internet Access
    • Sauna
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Book now for Christmas week. January and February weekends are filling up fast. House is perfect for your holiday celebration. We are near the slopes and have an exclusive parking pass for the two private ski lots. We have the Wintergreen Resort membership so you have access to resort facilities... View all property information
    Location Information
    Wintergreen, Virginia 22957
    5 of 5 bubbles Reviewed 25 June 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 away...
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    1 / 9
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 23831
    1 / 15
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Unique Benefits include passes and close proximity to the summer-time pool, the Shamokin Nature Preserve, the Nature Foundation, the Post Office, the Spa, and a dog park. This home is on the Mountaintop part of Wintergreen, near Sherando Lake (a National Park), the Blue Ridge Parkway and The... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 24
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Sauna
    • Shared Outdoor Pool...
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The ultimate Blue Ridge Mountain getaway in Wintergreen, Virginia awaits you at this 3-bedroom, 2-bathroom house with awe-inspiring views of the mountains. 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... View all property information
    Location Information
    Wintergreen, Virginia 22967