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, 176 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

Outdoor spacesWalkabilityLong stay

Bungalow in Winston-Salem

The kitchen features granite countertops and stainless steel appliances, with a spacious island and seating. A dining area with a table and chairs is visible in the background, illuminated by natural light through nearby windows.

Renovated Perfection in Quiet W-S Neighborhood

Open floor plan, beautifully renovated, brick home is the perfect place for you and your guests to spend time. Comfortable, home away from home is beautifully and comfortably decorated. Central heat and air conditioning. Updated stainless steel appliances and quartz countertops welcome you to the kitchen, which flows seamlessly into the dining and living rooms. Large screen TV in living room and also in master bedroom. 4th bedroom is the basement where there is a double bed. Dogs allowed.

WalkabilityOutdoor spacesParks

4.91 out of 5 average rating, 413 reviews

A living area features hardwood flooring and natural light from multiple windows. A comfortable sofa with decorative pillows faces a simple coffee table and a modern TV stand. A bright accent chair adds a pop of colour, creating a welcoming space.

4.95 out of 5 average rating, 223 reviews

House in Washington Park, historic Winston-Salem

I love my neighborhood! Newer Location for me! Relax with the family at this peaceful place to stay! If you are just passing through or traveling for work, this is the perfect place for you! Located in Washington Park (which is just 2 miles from Downtown), you will have easy access to all Winston has to offer! I also own Hoots Beer Company, and I will be happy to give you a beer tasting! If you see a concert you want to attend at my place, a free ticket is on me! Side note: NO PARTIES!

Outdoor spacesPetsGetting around

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, 130 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.

PetsWalkabilityCheckout

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, 129 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

Outdoor spacesPetsCheck-in

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.

4.95 out of 5 average rating, 236 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.

WalkabilityOutdoor spacesCheck-in

4.93 out of 5 average rating, 123 reviews

Idlewilde Farmhouse | 4BR/3BA Walk to Wake Forest

A modern farmhouse for groups visiting Wake Forest University and The Grounds — 4 bedrooms, 3 full baths, sleeps 10. 106 reviews at 4.93★. Stone fireplace, chef's kitchen, two private bedroom suites, hardwood floors. Walking distance to Allegacy Stadium, Couch Ballpark, LJVM Coliseum, and the new Grounds retail village. Need more space? We also offer this home combined with the back cottage for up to 16 guests with the whole property to yourselves. Pet-friendly. Superhost.

Outdoor spacesWalkabilityLayout

4.99 out of 5 average rating, 143 reviews

Cottage in Winston-Salem

Sleepy Bee Cottage, 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 gardens. 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. A small seating area beneath a mature dogwood tree offers a peaceful spot to relax. Welcome to the Carolina Cotswolds!

PetsWalkabilityBathroom

The modern kitchen features white cabinetry and a bold patterned backsplash. Stainless steel appliances, including an oven and dishwasher, are present. Natural light enters through two windows dressed with wooden shades. Open shelving displays glassware and plants, contributing to a fresh and functional environment.

4.97 out of 5 average rating, 103 reviews

Historic West End Haven, walk to downtown Winston

3 bdrm 2 bath duplex located in the historic West End district of downtown Winston Salem. This historic 1913 home has been completely renovated. Features a side porch with a view of downtown and rear deck. Convenience, convenience convenience.... Walking distance to the Arts District as well as multiple restaurants, bars and local shops. Minutes from Wake Forest, NC Baptist Hospital, BB&T Field. Includes Washer/Dryer, Cable TV and high speed internet.

WalkabilityOutdoor spacesBathroom

Townhouse in Winston-Salem

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

Prime Location, Comfort, and Convenience Await You! Why staying with us? - NEW: Fully kitchen renovated and well equipped. - Amenities are provided. - Serta & Bessatt mattress. - Smart TVs equipped with Netflix. - 10 min WALK along the sidewalk to WFU Campus (2min drive). - 5 min drive to Downtown. - 3 min WALK to Wake's Stadiums, LJVM Coliseum (A block away), skip parking hassles. - Across from THE GROUND. - 5 min DRIVE to Reynolda village.

PetsOutdoor spacesNearby

4.93 out of 5 average rating, 112 reviews

4.89 out of 5 average rating, 114 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.

PetsWalkabilitySolo travel