We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Winston Salem

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €110 Average
    |||
    |||
    €0€1,000+
    Suitability
    Suitability
    More filters
    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 21 Rentals in Winston Salem
    Sort by:
    Default
    New 3BR & 3BA !No Smoking!Pets $40! A single family home in convenient location.1 / 13
    (1)Excellent
    Winston Salem
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Winston Salem
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Winston Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Winston Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This James Bond inspired secret hideaway welcomes you with a comfy vibe. In historic upscale Buena Vista, its central location means you're 5 minutes from Wake Forest University, Downtown, Old Salem, NC School of the Arts, Trader Joe’s & Whole Foods. A private, inviting cottage surrounded by trees...
    View all property information
    Location Information
    Winston Salem, North Carolina 27104
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Winston Salem
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Private Garden
    • Washer
    • Cable/satellite TV
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Old Salem and its shops and restaurants, Cobblestone Farmer's Market, Granville Park, Washington Park, and the attractive, shady Strollway leading to downtown. Unwind on the home's lovely front porch swing, or spend time with family and friends on the expansive back deck, which overlooks...
    View all property information
    Location Information
    Winston Salem, North Carolina 27101
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Winston Salem
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Winston Salem, North Carolina 27104
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    Winston Salem
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Winston Salem, North Carolina 27103
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    Make Enquiry
    Winston Salem
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Winston Salem, North Carolina 27127
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    The following rentals are within 40 kilometers 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
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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!
    See all reviews
    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...
    View all property information
    Location Information
    Jamestown, North Carolina 27260
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Beautiful House 10 Minutes From I-40,85 & Airport.1 / 23
    (4)Excellent
    High Point
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Children's Pool
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2018
    The house was beautiful and comfortable! It had everything we needed, including an outdoor area to gather! We had family coming from CT, RI, NH, GA & KS for my daughters...
    Reviewed 31 December 2017
    We stayed here during Christmas, 2017 while visiting my wife’s parents. The total cost for this six bedroom house was comparable to what we would have paid for a hotel for our...
    See all reviews
    About this property
    House is located in the very high end cozy neighborhood, High speed gigabit wireless internet, Cable TV, Fully automated with CPI security with 2 Surveillance cameras out side and one door bell camera by ringcom Large projection HD Theater. Main level has one bedroom with attached full bath,office...
    View all property information
    Location Information
    High Point, North Carolina 27265
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Save time - get the best Winston Salem rentals sent straight to your email!
    Get the List
    Downtown Renovated 1906 Queen Anne1 / 18
    (1)Excellent
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    My sister, daughter and I enjoyed our quick stay here at Barbara's condominium. She and her husband met us upon arrival and gave us a quick tour of the place as well as...
    See all reviews
    About this property
    Spacious, quiet, all amenities. Our home was converted into a duplex many years ago. Our listing is the whole upstairs unit. 950sf, 2BR, 1Bath, LR, full Kitchen. Fully furnished, WiFi, everything included. Separate entrance, complete privacy. And even a front porch swing! All Downtown activities...
    View all property information
    Location Information
    Greensboro, North Carolina 27401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    The Owl's Nest- private country cottage on 10 acre horse farm in the Triad1 / 10
    (2)Very good
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Parking
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2017
    Quiet, peaceful, and great for family gatherings! Very clean, well-kept, and well-equipped. Definitely recommend!
    Reviewed 9 May 2017
    This is such a nice, clean, well-appointed cabin. The bed was so comfortable and each morning I sprang to the windows to look at the incredible view of horses in a field of...
    See all reviews
    About this property
    The Owl's Nest provides a cozy setting to relax and unwind. This house provides all the comforts of home while offering the unique experience of rolling hills, quiet breezes, and star-lit nights. Located on a 10 acre horse farm along with the hosts' home. Minutes away from I-40 and I-85....
    View all property information
    Location Information
    Greensboro, North Carolina 27406
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Luxury on the Lake - Perfect for Wedding Families1 / 19
    (1)Very good
    Greensboro
    7 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2018
    Overall a very good experience, good localization. The house was clean but it does need some renovation in the near future. Nothing mayor thought.
    See all reviews
    About this property
    ** Please read description in its entirety as it answers a lot of FAQ** This beautiful house is located in Greensboro, NC with its back to a private golf course and beautiful lake. The house features 7 bedrooms and 6 1/2 bathrooms and sits on 2.5 acres of land. It can be used for functions like...
    View all property information
    Location Information
    Greensboro, North Carolina 27410
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 24
    Make Enquiry
    Lewisville
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    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 20 minutes away. You’ll also...
    View all property information
    Location Information
    Lewisville, North Carolina 27023
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    Home Away From Home Charmer1 / 42
    (1)Average
    Kernersville
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2018
    I recently stayed at the home away from home during mlk weekend. I did not like that the pictures make it seem as if there are two separate rooms and a living room. It is more...
    See all reviews
    About this property
    Convenient to the triad. Winston-Salem, Greensboro, High-Point. This place is for everyone. With a king bed, a full bed, a queen air mattress, two couches, a full bath, WiFi, Netflix, a 55 in flat-screen TV you have it all! There is a big back deck for grilling or relaxing. The coffee bar is great...
    View all property information
    Location Information
    Kernersville, North Carolina 27284
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Kernersville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is on half an acre in Kernersville. It has been remodeled from top to bottom with beautiful lighting and the inside is like a rustic cabin. I provide all necessities like clean towels, soap, shampoo, tooth brush in case you forget. The house is smoke free. The house is conveniently located...
    View all property information
    Location Information
    Kernersville, North Carolina 27284
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Jamestown
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Jamestown, North Carolina 27282
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
    Make Enquiry
    Greensboro
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Greensboro is an interesting city to visit and explore. There are parks, a good down-town with plenty of restaurants, brew-pubs etc. and there museums, including the Civil Rights Museum (ex Woolworths). My house is close to downtown, to a stream and walking/running path, and I provide bi-cycles for...
    View all property information
    Location Information
    Greensboro, North Carolina 27401
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Greensboro getaway awaits you at this spacious and open 2-bedroom, 1-bathroom vacation rental house, which features accommodations for 5 guests. The property boasts fantastic amenities and is located in a peaceful, quiet neighborhood, fit for an unforgettable stay! Boasting 1,500 square feet...
    View all property information
    Location Information
    Greensboro, North Carolina 27405
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Greensboro
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1 bedroom, 2 bath contemporary apartment located in the heart of downtown Greensboro. Walking distance to scores of restaurants and bars, the ballpark and the Performing Arts Center (currently under construction). Don't miss the International Civil Rights Museum or any of the many...
    View all property information
    Location Information
    Greensboro, North Carolina 27401
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Greensboro
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your next getaway to North Carolina's heartland region by staying at this gorgeous Greensboro vacation rental condo. Situated right downtown in the charming Southside community, this condo offers ultimate easy access to Greensboro's most notable attractions! Featuring 2 bedrooms, 2...
    View all property information
    Location Information
    Greensboro, North Carolina 27406
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property
    Owner log in