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.

Winston Salem Vacation Rentals

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
    Price
    per night
    $158 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Winston Salem area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Winston Salem
    Sort by:
    Default
    New 3BR and 3BA Single Family Home1 / 13
    (1)Excellent
    Winston Salem
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Winston Salem
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Winston Salem
    2 Bedrooms, 1 Bathroom, Sleeps 6 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
    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
    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
    The following rentals are within 40 kilometres of Winston Salem.
    Awesome Luxury Cabin Retreat Near Pilot Mountain1 / 12
    (9)Excellent
    Pilot Mountain
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Porch
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    This is a great cabin in a great location. We were a family of 6 and had plenty of room to spread out. The room sizes are generous and there is a huge deck with comfortable...
    Reviewed 11 April 2017
    Incredible views from the front porch and even better if you walk up the hill in the back. Beautiful place inside and out. Great 3 bedroom layout: 1 master downstairs with queen...
    See all reviews
    About this property
    For a truly rejuvenating, quiet and relaxing experience, Pilot's Peak Cabin Retreat is the place. Nestled amidst 50 acres of amazing beauty and stunning views, just minutes from the wonderful attractions of the region: Pilot Mountain State Park, Yadkin Valley wineries, hiking trails, biking, zip...
    View all property information
    Location Information
    Pilot Mountain, North Carolina 27041
    Cabin Holiday Rental - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    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
    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
    3 BR home great Nhood near UNCG, Coliseum,downtown1 / 13
    (7)Very good
    Greensboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Porch
    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2017
    loved our stay in Greensboro . This house was perfect. We would definitely love to stay again. House had everything we needed to enjoy our stay. Thank you .
    Reviewed 1 November 2015
    Traveled with my family to a wedding. It was a very clean, nice house. It felt like home while we were there. The neighborhood was beautiful. Would stay there again if we...
    See all reviews
    About this property
    3 Bed 1 Bath brick home in a wonderful neighborhood. 2 miles from downtown, coliseum & UNCG. Friendly shopping center is 1.5 miles, the home is right in the middle of Greensboro, you can get anywhere in 15 mins, to High Point furniture market in 20 mins. Across from the arboretum and walking...
    View all property information
    Location Information
    Greensboro, North Carolina 27403
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Beautiful House 10 Minutes From I-40,85 & Airport.1 / 23
    (1)Excellent
    High Point
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    My family , friends and I had a most relaxing time at this house. The host was very inviting and we enjoyed the stay. The home was beautiful.
    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, Large projection HD Theater. Main level has one bedroom with attached full bath,office room, living room with full sofa, Large flat screen 65'TV, Dining...
    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
    Pfafftown
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Secure Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Feels like home. Peaceful, quiet & friendly. Close to hospitals, shopping $ restraunts. Full use of kitchen and dinning rm & deck. Wr also have gas grill I have outdoor cat that does not come in house The space It has large oak entertainment center with large TV, Dish network lots of space for...
    View all property information
    Location Information
    Pfafftown, North Carolina 27106
    Condo/Apartment - 1 Bathroom, Sleeps 2
    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
    Pfafftown
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a room with twin bed. It has kitchenette with sink, frig, microwave, griddle. It includes dishes and linens. It is in a quiet neighborhood with private entrance. Shopping & restaurants 1 mile away. Near Wake Forest University,Old Salem, Forsyth and Baptist hospitals. Air matteress available...
    View all property information
    Location Information
    Pfafftown, North Carolina 27106
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Greensboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Washer
    • Balcony
    • Wi-Fi
    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear traveling guest! Thank you for your interest in my house. I hope you will be pleased with my terms and intrigued by the many pictures you will see.I hope to meet and exceed your needs for a place to call home away from home. I look forward to hosting guests from around the world and to make...
    View all property information
    Location Information
    Greensboro, North Carolina 27407
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    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
    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 6
    Make Enquiry
    Greensboro
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Outdoor Dining Area
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear traveling guest! Thank you for your interest in renting a room in my house. I hope you will be pleased with my terms and intrigued by the many pictures, to book your needs, for a place to call home from me.Even though you just book a room,most times you will have the entire house to your...
    View all property information
    Location Information
    Greensboro, North Carolina 27407
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    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, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    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
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    • DVD Player
    • Patio
    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
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Jamestown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Kernersville
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    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
    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
    Greensboro
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Shared Garden
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear traveling guest! Thank you for your interest in renting a room in my house. I hope you will be pleased with my terms and intrigued by the many pictures, to book your needs, for a place to call home from me.Even though you just book a room,most times you will have the entire house to your...
    View all property information
    Location Information
    Greensboro, North Carolina 27407
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Kernersville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is on 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. I prefer home rental or a Bed and Breakfast type rental....
    View all property information
    Location Information
    Kernersville, North Carolina 27284
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Greensboro
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your peaceful getaway awaits you when you stay at this 2-bedroom, 1-bathroom vacation rental house in Greensboro, which accommodates 4 guests. 'The Blue House' boasts over 1,300 square feet of space, wood-burning fireplace, and private deck surrounded by lush trees. Whether you choose to stay in or...
    View all property information
    Location Information
    Greensboro, North Carolina 27408
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property
    Owner log in