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Holiday Homes in Winston Salem

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    Don't let other travellers get your favourite Winston Salem area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Winston Salem
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    Winston Salem
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Winston Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winston Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Winston Salem
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Housekeeping Included
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It was a big family room, now converted into a bed room. Has a queen bed can sleep two, also in the room have two recliners, can sleep two more incase of family gathering. Has central electric heat and air, wood burning fireplace for display, and electric fireplace to enjoy. Bathroom has two...
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    27104, Winston Salem, North Carolina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Winston Salem
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    • Patio
    • Balcony
    • Terrace
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Newly Added Amenities*** - Washer/Dryer on Premises - Pool Access - Gym - Billiards & Game room - BBQ Grill NEW upscale 1 bedroom apartment located on the West side of Winston Salem. The apartment is fully furnished and equipped with super high speed internet. Furnished with a Couch, Queen...
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    27103, Winston Salem, North Carolina
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    Winston Salem
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great neighborhood by WFU (Wake Forest University)/ Reynolda/ Graylyn. The rental is separated from host side of the home and private. You have private front door entrance with 2 rooms; hallway and full bath. It’s clean, simple and safe. Host provides luxury towels, toiletries and a super...
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    27106, Winston Salem, North Carolina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Winston Salem
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Step back in time with this adorable vintage Serro Scotty. This 60's camper is the perfect escape and loaded with charm; you will be the talk of the campground! This cute little camper will be set up at the location of your choice within 50 miles of beautiful Winston-Salem NC, all you have to do...
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    27127, Winston Salem, North Carolina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    The following rentals are within 30 kilometres of Winston Salem.
    Home Away From Home...High Point, Greensboro, Winston Salem, Kernersville1 / 39
    (1)Excellent
    Jamestown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    Tiffany was great and we had everything we needed. Lots of room for the grandbabies to play! Will stay here again!
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    About this property
    Beautiful 4 bedroom home located in a quiet cul-de-sac. Great for business travel as well as friends and family gatherings. Only 4.2 miles to High Point University, 4.49 miles to the High Point Furniture Market, 6.0 miles to the Sedgefield Country Club, 13.5 miles to the Greensboro Coliseum...
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    27260, Jamestown, North Carolina
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Lewisville
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On your next trip to Lewisville, North Carolina, don’t hesitate to book this 5-bedroom, 3-bathroom vacation rental house that accommodates up to 14 travelers. Enjoy a game of pool at the private billiards table after shopping & dining in historic downtown Winston-Salem 17 miles away. You’ll also be...
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    27023, Lewisville, North Carolina
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Kernersville
    3 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Balcony
    • Washer
    • DVD Player
    • Grill
    • Central Heating
    • Terrace
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is centrally located between Greensboro and Winston-Salem. I am only a short distance from A&T, High Point University, UNCG, the Greensboro Coliseum, Winston Salem State, and only 15 minutes from downtown. The home has been completely remodeled and has lots of amenities. I take pride in...
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    Location Information
    27284, Kernersville, North Carolina
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 16
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    Kernersville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take in the air on the sundeck of this renovated 2008 brick home. Inside, the neutral tones and warm light coming through the windows provide a soothing environment, while the kitchen has commercial-grade appliances and marble counter tops. Lovely, modern, bright space. Homely while remaining...
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    Location Information
    27284, Kernersville, North Carolina
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Classy, Cozy Close to Everything1 / 23
    (1)Terrible
    Deep River
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Houses is located in the very high end cozy neighborhood. High speed wireless internet, Cable TV,. Main level has one bedroom with attached full bath, office room, living room with full sofa, large kitchen. Great patio with seating, swing and gas grill. Upper level has beautiful master bedroom with...
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    27265, Deep River, North Carolina
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
    Jamestown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Balcony
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The jewel you've been waiting for! Welcome to Jamestown where you will enjoy brick sidewalks and street lights. Wonderful four bedroom house, with huge deck, spacious and secure parking facility right in the middle of everything. This house surely retains the value of peaceful living while...
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    27282, Jamestown, North Carolina
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    High Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Balcony
    • Terrace
    • Patio
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful renovated 1930 cottage with vintage furnishings and original heart of pine floors and beadboard ceilings. Full laundry on site and wonderful front porch and back deck overlooking 1/2 acre backyard. Plenty of parking and great central location close to HPU, new BB&T Stadium, downtown,...
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    Location Information
    27262, High Point, North Carolina
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Deep River
    6 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    House is located in the middle of town, 10 minutes drive to High Point furniture Market, High Point University and High Point Theater, the world's largest furniture Land South showroom is close by. Many eating places like Apple Bees, Texas Stack House and many fast food spots. PTI Airports, Major...
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    27265, Deep River, North Carolina
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 18
    Jamestown
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Hot Tub
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Although small, this extended-stay hotel has many great features! It is child-friendly, very comfortable, and even has a waterbed! You really can't go wrong. Renters must be pre-approved before scheduling, and a minimum of 38 weeks stay is preferred. This room can fill up quick, so please...
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    27282, Jamestown, North Carolina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
    Wallburg
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the wonders of Winston-Salem like never before from this revived vacation rental! This historic barn boasts 3 bedrooms, 3 baths, and an open interior dotted with elegant treasures and antique accents. Spend mornings watching the farm animals roam from your private balcony or patio, and...
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    27107, Wallburg, North Carolina
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Summerfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a quiet neighborhood, this newly remodeled 3-bedroom, 2-bath Greensboro getaway is the perfect Heartland host for 8! The property boasts brand new furnishings, a spacious sunroom and a large yard for entertaining. A quick 6-mile trip away, downtown plays host to dozens of local...
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    27410, Summerfield, North Carolina
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Deep River
    1 Bedroom, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your stay in historic Jamestown at this family-friendly 3-bedroom, 2.5-bath vacation rental house for 8. You'll feel right at home in the 2,800-square-foot property boasting an expansive deck, a full kitchen, and free WiFi. This property is located 20 minutes from the heart of downtown...
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    Location Information
    27282, Deep River, North Carolina
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 8
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