
Holiday rentals in Winston-Salem
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Top-rated holiday rentals in Winston-Salem
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The Zen Ranch - Spacious Layout with Modern Decor
1960s ranch style home on 2 acres with 2,400ft² interior. This home has been fully remodeled with a large open floor plan and all modern amenities and decor. With ample yard and patio space, large bedrooms, bonus room and 3 full bathrooms there is plenty of space to spread out. • Abundant Natural Lighting • Backyard w/ patio + fire pit + hammocks • Comfy Beds • Fully stocked Chefs Kitchen • Large Private Deck + BBQ grill • Indoor fireplace • 400Mps WiFi • 3 x 4K TVs w/ Disney, Netflix & Prime

The Foothills in Downtown WS! Renovated | King Bed
Your downtown getaway awaits at the SUMMIT @ West End! Walk to endless restaurants, bars, shops & entertainment throughout beautiful, downtown Winston! Relax in our fully renovated space, designed with comfort & creativity in mind. Enjoy on-site parking & laundry, deluxe coffee/tea station, premium KING mattress & linens, smart TVs in living room & bedroom, high-speed Wi-Fi & more! 3 min to Millennium Center 5 min to Wake Forest Baptist Health 7 min to LJVM 8 min to Novant Health 8 min to WFU

Log Cabin in the city
READ ENTIRE LISTING! NO PARTIES/ GATHERINGS. Only the guests on the reservation are allowed to be on my property. I WILL KICK YOU OUT AND CALL THE COPS. I DO NOT PLAY GAMES. The listing is the entire UPPER LEVEL of my log cabin, which is conveniently located less than a mile from Downtown Winston-Salem! The back yard is surrounded by woods and a privacy fence! Great place close to downtown. NO SMOKING of any kind allowed anywhere. Pots and pans are available. No salt and pepper or condiments

Private, Peaceful, Green Hideaway 6 Minutes to WFU
Just minutes from Wake Forest, we have a completely remodeled this very special place. We have often stood at the huge windows of this ground level space and watched mother deer with their fawns play in the yard. Your home away from home is at the end of an already quiet cul-de-sac so traffic noise is zero. Your suite is completely private with its own ground level entrance. Your kitchen has a full size sink, an induction stove, fridge, with all your cookware, dishes. New bath with tub.

K obscura
Historic loft in Downtown Winston Salem's Innovation Quarter. Located above Krankies Coffee near WFB Medical School and Bailey Park.Short walking distance to several restaurants and bars. This space has private entrance and patio. Includes gift card for coffee at Krankies. Note there is a train that passes by a few times a day and at night. We do allow pets but have a fee. Includes deep soaking tub, mini-kitchen and comfy king-size bed. Space is accessed via stairs. Parking included.

Dragonfly: 1 Br Garden Apt Near WFU & Baptist Hosp
The "Dragonfly" is a spacious, peaceful 1BR garden terrace apartment (800 sq ft) in one of Winston-Salem’s most desirable neighborhoods. Just 1 mile from Baptist Hospital, 4 miles from Wake Forest University, and 10 minutes from downtown, this light-filled retreat is perfect for medical travelers, university visitors, couples, or small families. Features a king bed, washer/dryer, workspace with fast Wi-Fi, kitchenette, and private patio with garden views. Hi-chair & Packngo for families

Entire COZY Unit - 3 min walk to WFU.
Welcome to your cozy - little net. Please keep in mind that this unit is attached to our house (we shared a wall - different entrance). Everything showed in the pictures will be all yours (Master bedroom, Study room - living room Space, and an extraordinary bathroom). 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 and Restaurants. - 10min drive to Wake Forest Baptist Hospital. - Reynolda House museum.

Old Salem Getaway - Visit DTWS via the Strollway
We love our comfy third floor condo with elevator access. Whether you are in town for business or pleasure, this condo fits the bill. Walk to Old Salem, UNCSA, and Salem College. Jog or bike Salem Creek trail, which is at our doorstep. Stroll through Old Salem on your way to downtown’s amazing eateries and breweries. Close by are Wake Forest University, WSSU and downtown Winston-Salem, and hospitals - this condo is central to anywhere in the Winston-Salem area.

Bright and refreshing apartment in Ardmore
Our studio apartment is located in the heart of Historic Ardmore. We are 5 minutes from both Novant and Atrium (Baptist) hospitals, 7 minutes from downtown Winston Salem and 10 minutes from Wake Forest University. The apartment is totally private, quiet and furnished to be comfortable for either a short or long term stay! Enjoy our safe, walkable neighborhood as well as easy and close access to the major highways.

“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!

Charming quiet condo all to yourself
This is a cozy non pet condo for two. Perfect for extended stay hospital visits. Next door to Novant Health care and 1.5 miles from Baptist Hospital. Grocery and restaurants in walking distance. Will meet new guests in person. A few easy steps to the lower level then flat up to the door. Non-smoking. No pets. Contact host in message box for availability.

Urban oasis in downtown W-S; sparkling clean
Top unit of a three-family house, this 1000 sq ft. 2 bedroom, 1 bath apartment is in the heart of downtown Winston-Salem. Please review our house rules before you book. It is an ideal location two blocks away from all of the action of Fourth and Trade Streets, tucked into a funky, tree-lined neighborhood that is quiet and private.
Popular amenities for Winston-Salem holiday rentals
Other great holiday rentals in Winston-Salem

Private bedroom 5 mins from Wake Forest Hospital

Easy stay. Room #3

VHS Suite, West Salem Art Hotel

Thirsty Thistle Tiny Cabin

Quiet in Kernersville with Queen Sized Bed

Rosy’s House

Quiet, Spacious Suite with Private Entrance

One bedroom studio hosted by Gina
Quick stats about holiday rentals in Winston-Salem
Total rentals
1K properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
46K reviews
Family-friendly rentals
560 properties are a good fit for families
Pet-friendly rentals
390 properties allow pets
Rentals with a pool
70 properties have a pool
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- North Carolina Zoo
- Wet'n Wild Emerald Pointe Water Park
- Hanging Rock State Park
- Pilot Mountain State Park
- High Meadows Golf & Country Club
- Sedgefield Country Club
- Dan Nicholas Park
- Meadowlands Golf Club
- Stone Mountain State Park
- Greensboro Science Center
- Old Town Club
- Lake Norman State Park
- Divine Llama Vineyards
- Starmount Forest Country Club
- Lazy 5 Ranch
- Mooresville Golf Course
- Olde Homeplace Golf Club
- International Civil Rights Center & Museum
- Gillespie Golf Course
- Raffaldini Vineyards & Winery
- Childress Vineyards
- Shelton Vineyards
- Guilford Courthouse National Military Park
- Autumn Creek Vineyards