Pet-friendly holiday rentals in Winston-Salem

The charming exterior of a single-story home is presented, featuring a bright red front door. Flanking the entrance are two symmetrical windows, while landscaped bushes and a path lead to the porch. A tree provides shade, enhancing the welcoming appearance.

4.94 out of 5 average rating, 173 reviews

The Walnut Cottage. Charming! Near Everything!

Relax in the historic West Salem district. Central to UNCSA, WSSU, WFU, Carolina University, hospitals, downtown, dining, shopping, parks/greenways and 18th century town of Old Salem. Enjoy cozy seating areas, or head out to the patio, relax on the screened porch or grill on the deck. Off street parking, WiFi, smart TVs in each room, updated kitchen with gas range. 2nd living room in mini suite with workspace and Ethernet port. Beds: 2 queens, 1 full and 1 futon. Keyless entry. Washer/Dryer

A single-family ranch home is showcased with a stone accent exterior, surrounded by well-maintained landscaping. A paved driveway leads to the entrance, while trees and flowering plants add natural beauty to the front yard.

4.98 out of 5 average rating, 129 reviews

Elegant Pet Friendly Ranch close to everything!

Our sun filled updated 1950's single family ranch home in a quiet and beautiful neighborhood has all the comforts needed for a long or short stay. Fabulous location-just minutes to multiple universities, hospitals, historic sites and downtown Winston-Salem. Nearby are plenty of restaurants, shopping and recreational parks. Piedmont Triad Airport in Greensboro is 35 minutes away. ***ALLERGY ALERT*** I do have the house professionally cleaned but dogs and cats do stay here occasionally.

An open living area is shown, featuring a foosball table in the foreground. A cozy seating arrangement is visible, complemented by a stone accent wall and large windows. Light-colored walls and warm wooden flooring enhance the inviting atmosphere of the space.

4.87 out of 5 average rating, 126 reviews

Downtown Charm, 3 Bdr, Near Rest and Bars

Explore Winston-Salem - our cozy 3-bedroom, 2-bath home, a short walk to bars, restaurants, and a famous brewery. Enjoy stylish comfort with TV-equipped bedrooms, a game area with foosball, and an outdoor fire pit. The fully equipped kitchen and dining area cater to your culinary needs. Located in downtown, it's your ideal base for city adventures. Amenities include WiFi, cable TV, essentials. Perfect for any visit, experience downtown charm and convenience in your home away from home

4.99 out of 5 average rating, 141 reviews

Cottage in Winston-Salem

Sleepy Bee Cottage, simple charms, near WFU

Feels like the countryside within city limits. This cottage sits on shared property with the owners’ home and overlooks more than an acre of woodland, with a small garden just out front. Beyond the energized deer‑protection fence lies a Duke Energy easement and a wooded ravine, giving the property a quiet, tucked‑away feel. Guests have ample, well‑lit parking, along with access to a fenced dog yard. A small seating area beneath a mature dogwood tree offers a peaceful spot to relax.

The main bedroom features a sizable bed with a dark gray throw and neatly arranged towels. Two bedside lamps provide soft illumination beside the bed. The room is complemented by two framed artworks, and a bathroom with glass door access is visible in the background.

4.96 out of 5 average rating, 233 reviews

Beautiful 2 BR home with Office and Game Room

This beautifully decorated 2 bedroom home, part of a duplex, comes with high-speed Internet and Wi-Fi. It includes an office and a game room. It is near shopping, hospitals, and the rest of the Winston-Salem scene. The kitchen has all the tools needed to prepare your favorite meals. The TV in the living room includes Disney+. Everything except the game room is on the main level. The back deck is ready for hosting a barbecue, with a view of the backyard and adjoining green space.

A well-appointed bedroom features a spacious bed with blue bedding accented by two orange throw pillows. Above the bed, two framed art pieces are displayed. A small round nightstand with a marble top is positioned beside the bed, and warm curtains frame the window.

4.9 out of 5 average rating, 153 reviews

Sleeps 12 | 4BR Walk to Wake Forest & Grounds

One of the largest and most-reviewed homes near Wake Forest University — 145 stays at 4.92★, top 5% Guest Favorite. The Polo sleeps 12 across 4 bedrooms (3 queens + 4 twins) plus a sofa bed. Walk to Wake Forest University and The Grounds entertainment district, with steps to Allegacy Stadium, Couch Ballpark, LJVM Coliseum, and the new retail village. A classic brick home in a quiet residential pocket, with a dedicated workspace and self check-in. Pet-friendly.

4.88 out of 5 average rating, 112 reviews

The bedroom features a spacious bed dressed with soft linens, flanked by two nightstands with lamps. Large windows are adorned with light curtains, allowing natural light. A cozy area rug lies beneath a vintage bench, while an antique mirror adds character to the room.

Flat in Winston-Salem

Light & Bright West Salem 2nd Floor Apartment

This beautifully decorated, second floor apartment in a lovely, 100 year old historic home is perfect for short or extended stays. Self check-in via smart lock, fast wi-fi, dedicated living room, kitchen, bedroom, and small office. High ceilings and many windows. Walk a few blocks to Old Salem or Truist baseball stadium or take a quick ride to area hospitals and colleges. Plenty of street parking, laundry room on site.

4.95 out of 5 average rating, 334 reviews

A cozy bedroom is presented, featuring a spacious bed adorned with a rust-colored quilt. A decorative lamp casts light beside a dark wood nightstand, accentuated by sculptural art pieces on display. A soft texture of a woven rug completes the inviting atmosphere.

Flat in Winston-Salem

West Salem Art Hotel, "Art"partment #1

Welcome to the West Salem Art Hotel! This eclectic and beautiful apartment is located in a 1931 historic brick building only 1 mile from Downtown Winston-Salem! All the conveniences of staying JUST on the outskirts in Historic West Salem, without all the city noise, AND located in the middle of a peaceful urban garden! We are minutes away from the best eateries/entertainment W-S offers! Private, unique, and clean.

Townhouse in Winston-Salem

A comfortable bedroom presents a spacious bed dressed in earthy-toned linens, flanked by two vibrant red nightstands. Above the bed, a modern piece of abstract art adds visual interest, while natural light filters in, highlighting the soft textures of the bedding.

4.93 out of 5 average rating, 109 reviews

Heart of Winston - Walk to Stadium/ Close to WFU.

Prime Location, Comfort, and Convenience Await You! Experience the ease of front door parking, indulge in the luxury of a premium Serta & Bessatt mattress paired with high-quality linens, unwind with smart TVs equipped with Netflix. When staying at our place, you are: - 3 min drive (10min walk) to WFU Campus. - 5 min drive to Downtown. - 3 min WALK to Stadiums. - 5 min drive to Reynolda village.

The living room features a spacious blue sectional sofa adorned with light cushions. A round coffee table sits at the center, complemented by a small lamp nearby. A ceiling fan provides airflow, and a cozy area rug adds warmth to the hardwood floor.

4.9 out of 5 average rating, 443 reviews

House in Historic Sunnyside W-S

Beautiful home in Winston-Salem located just minutes from downtown, hospitals and all of the colleges the area has to offer! You and your family will enjoy this spacious 3 bedroom home with easy access to nightlife, all tourist attractions and great food options! If you need suggestions in the area, I can give you a great list! No parties, gatherings or unauthorized guests allowed on the property!

A single-family home features a light-colored exterior with blue shutters. A large, attached garage is visible, with a paved driveway leading to it. The front yard is well-maintained, showcasing shrubs and a tree with vibrant autumn foliage.

4.93 out of 5 average rating, 231 reviews

"Deacon House" 3 bedrooms

Looking for a place to stay in Winston Salem? Check out this 1,315 sqft. single family home that has 3 bedroom and 2 full bath. It has its own driveway with 2 car garage attached and fenced in backyard, guest occupy the entire house except the attic. It is just a few minutes away from downtown, Wake Forest University, Reynolda Garden, LJVM coliseum, Starbucks and grocery stores.