Guesthouse holiday rentals in Winston-Salem

Gate House Garden

Walk down the path to your mini suite: a cozy studio with an open floor plan, kitchenette (microwave & toaster over), clawfoot tub with shower, queen bed, & private deck. Great for 2 guests or place to work remotely. A 5-min walk to scenic lake/trails. In a very quiet neighborhood, it's not a good fit for gatherings or folks coming & going at all hours. Please no smoking/vaping of any kind in/on premises. 10 min drive to GAC, Tanger, UNCG, A&T, Coliseum, Guilford College & 25 mins to High point.

Stylish Hamilton Lakes Studio Facing Park/Trails

Private keyless entry to 2nd floor garage studio apartment in prestigious Hamilton Lakes. Space is one large room with a kitchen w/bar next to living area. Sleeps 4 (2 under 18) with queen bed, a twin and a sofa; 42" TV, SMART bluray, WIFI, NETFLIX, toaster oven, coffee maker, microwave, fridge, full bathroom with walk-in shower; washer/dryer in garage. Three miles of trails start across the street; 5 minute walk to the lake/playground. 3rd & 4th guests (must be under age 18) $20 each/night.

Carolina Cottage

Charming themed studio cottage, newly refurbished. Cozy space w/full kitchenette (loaded), charming breakfast table, special coffee/tea bar, comfy 2-seat sofa & large TV. Bright seating area w/ screen door to patio for fresh air, new queen bed with vaulted ceiling. Full modern bath-shower. Pets OK w approval, walkable historic Emorywood & HP Country Club neighborhood, near HPU, hospital, park, HP Library, farmers market & HP Furniture Market. Big yard, patio & gas BBQ. Week-longterm discount.

Sunset Hills Carriage House! King Bed

Industrial Chić Abode in Beautiful Sunset Hills! Close to Everything with all the comforts of home. The Carriage House offers a private self contained guesthouse located behind our house ( 485 sq ft studio ) Safe upscale neighboorhood. Comfy King Bed! We have a pullout Queen sofa bed available for extra guests! 2 car max, NO SMOKING OR PETS! Walkable to UNCG and 2 minutes from everywhere you want to be! Close to Lindley Park favorites at the corner, UNCG, Downtown and Greensboro Coliseum.

The Cottage at Haze Gray Vineyards

Ready for a romantic weekend getaway? Or just a break to get away to the country? This beautiful log cabin situated in a vineyard in the heart of the Yadkin Valley wine country. Our tasting room is situated on the other side of the vineyard where you can taste our wines made from the grapes we grow in our own vineyard. We are located close to several wineries in the local area. Other local Attractions include Rockford General Store, Pilot Mountain. Mt Airy or hiking at numerous parks.

The Bungalow at Weather Ridge

Kick back and relax in this calm, stylish space! Our private guest house is the perfect studio style space. COMFORTABLE queen bed, plus a futon for 3rd guest, dining, loveseat, full micro kitchen and full bathroom are all beautifully designed for your stay. Located at the back of acre lot in quiet, well established, neighborhood. Centrally location in the Triad: 10 minutes from Kernersville, 12 minutes from Winston Salem, 20 minutes from Greensboro, and 25 minutes from downtown High Point.

Bee Happy- Studio & Pets Welcome- No cleaning Fees

Welcome to the "Bee Happy" a self-check in retreat for anyone needing a clean, peaceful retreat to rest a weary head, visit locally or just get away from it all. Pets are always welcome and are as pampered as our guests (Please read our important Pet Policy below). Our large, private outdoor deck is complete with a small side yard and fenced for your pet's safety. Our neighborhood is beautiful, secluded and in a perfect location that is close to I-40, Parks, restaurants.

Mel’s country cottage. Country life near the city.

Private detached effeciency apartment in a country setting near WinstonSalem. Queen bed, kitchenette with sink and essentials, sofa, smart TV, full bath, covered porch. Relax by the creek or enjoy nature walks. Watch the occasional deer & other wildlife. Use the grill or fire pit at your leisure. Pets welcome. Local restaurant & convenient store 1 min. away. Close to many tourist destinations- Hanging Rock, Winston Salem, Pilot Mt. Belews Creek power station.

A charmer! Great spot near downtown.

A sunny garden studio in peaceful Fisher Park historic neighborhood that's an easy walk to downtown, restaurants/breweries, baseball stadium. Perfect location. Private with a separate entrance. One queen bed. Wifi. Plenty of on street parking. The kitchenette area has a microwave, coffee pot (I provide coffee/tea & water cooler), mini fridge w/ sm freezer. Private outdoor garden area with table, chairs & umbrella.

Beautiful Duplex

Please Read Before Booking: Maximum Occupancy: 2 Guests (Including Children) check in is at 3:00 PM. Check out at 10:00 AM. Enjoy a simple, peaceful stay in our centrally located duplex . We're just 15 minutes from UNC Greensboro, High Point University, the Greensboro Coliseum, Four Seasons Mall, Friendly Center, and both Downtown Greensboro and High Point. Downtown Jamestown is only 5 minutes away.

Private Guesthouse in a Quiet Neighborhood.

If you are looking to party, this is not your place. Our lovely and cozy detached suite is in a quiet residential neighborhood close to the charming restaurants and shops of Friendly Shopping Center. A short 13 min drive to downtown Greensboro and a short 12 minute drive to the Greensboro Airport. Perfect for tourists or business travelers who want to be able to see all Greensboro has to offer.

“Home” on the Road!

Have fun with the whole family at this stylish apartment situated on a beautiful 3.5 acre property! Massive walk in tiled shower with multiple shower heads. Friendly dogs allowed for $35 a dog. No more than 2 dogs. Must be left in a crate if left in apartment alone. We have a large crate available to use. We have a SUPER friendly 2 year old poodle/border collie mix that will greet you!