
Guest house holiday rentals in Winston-Salem
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Top-rated guest house rentals in Winston-Salem
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Winston-Salem
Family-friendly guest house rentals

The Friendly Place
The perfect spot for a weekend trip! Super close to downtown and close to restaurants. Host communicated throughly. The place was just like the photos and had everything we needed.

Studio 1BR near WFU
We had a great stay at Dave's place, very dog-friendly! It was spacious and good for our one-night stay. Our dog had plenty of yard to do her business and sniff around. Due to Dave's clear directions, we had no problem finding the place in daylight. Our event was at night, but we could also find it upon coming back to the apartment. Dave was friendly and welcoming, helping us to feel right at home.

Cozy Downtown Kernersville Carriage House
Angela was a great host and saw to everything we needed. She was always available to make sure our stay was great. Definitely recommend!

Courtyard Cottage Safe Parking! No pet fees!
What an adorable place! It is sweet and has everything you need. I’d stay there again in a heartbeat!

Stylish Hamilton Lakes Studio Facing Park/Trails
Fantastic location, beautiful decoration. Cozy, clean, comfortable. Super friendly hosts. Love staying at their locations.
Guest house rentals with a patio

3 mins from Downtown - PS5, King Bed & EV Charger
Amazing stay. Thank you for everything and it was a pleasure doing business with you.

Tranquil and private lower level apartment
I wouldn’t hesitate to stay again at Diane’s Airbnb. She and her husband were wonderful, responsive hosts. Their home is pristine and peaceful. I’d certainly stay there again…

Modern Country Studio w/Kitchenette | Dog Friendly
Ryan was wonderful! Super attentive and also was able to accommodate a slightly later check-out time. Any questions we had was responded right away. What a lovely spot, did not disappoint at all. It was so nice feeling like we were living in luxury for a night! Highly recommend!

The Little White House
Katherine’s place was perfect r for my needs. It was one of the best 1bdrs I’ve ever stayed in. I certainly hope to be back.

Woods Retreat
Ozzie was a wonderfully responsive host and checked in on us throughout the visit to ensure we were comfortable and happy. The house was beautiful and just as described in the listing. The setting is perfect for a quiet getaway.

City House in Forest 15 min downtown GSO, NC
Older home in a nice neighborhood but it has been fixed up and the house was nice and clean. Beautiful yard with all the trees and Dennis was always very responsive

The Stratford Guesthouse
Wonderful guest house with attention to detail. So clean and cute. Would love to stay again.

The Old Welding Shop
We loved everything about our stay and would highly recommend it. After a long drive, a wedding, and spending time doing activities in town, it was nice to come back to a quiet comfortable place to wind down. We did not walk the property but I'm sure it would have been beautiful. If you need easy accessibility for someone, it would be perfect. There was very flat parking right up to the door, no steps inside or out, no carpet, and a walk-in shower. If we ever needed to come to the area again, we would definitely stay here again.
Guest house rentals with a washing machine and dryer

Golden Studio, few minutes to Downtown.
Super nice little studio very quiet area

Backyard Pool House
We truly enjoyed our stay at Ben’s place. The house was very close to downtown and Old Salem for those visiting the area. We enjoyed the light and open feel of the house and wished it had been warm enough to enjoy the pool! Ben was very responsive and directions were clear even when arriving after dark. I would recommend Ben’s place as a quiet, clean space close to all.

Grandover Hideaway
I really enjoyed my stay, worth every penny. This is a safe location, in a really quiet and peaceful neighborhood. The air bnb had everything I needed for a month stay. Lindsay was very friendly and responsive , which is very appreciated. Only thing I would mention is the neighbor has a larger dog whose area can see into the yard of the air bnb.. I do have a dog that is rather reactive so we walked around the neighborhood when she needed to go outside. The owners do put the dog back in the house if he barks too much.

The Bunkhouse at Olde Stone Farm
It was a perfect stay. The location was wonderful and quiet, the house clean and organized, we had everything we needed, a fully equipped kitchen, and comfortable and warm beds. 100% recommended. Andi and Lori were very friendly, answered questions quickly, and were always attentive. Thank you so much for everything.

Luxurious guesthouse with gorgeous pasture views
Our experience at Southern C’s Farm started 3 weeks before we arrived. That was how much time we had to plan a wedding! Short engagement! When I reached out to Jenny, she was quick to respond and furthermore, she was able to provide such great guidance and advice. And when I had any questions or felt my stress level rising, Jenny is the one who gave me a sense of peace that once we got there, it would all come together. And it did! During our event, she was there to reassure me and to provide solutions for any little hiccup that came up! And we did have some! I can’t thank Jenny enough for being such a wonderful and resourceful host! She is a doer! The property, I can’t say enough! It is breathtaking and was the perfect place for our family. We felt safe was was very comfortable! Very clean. I only wish we could have stayed longer! A huge heartfelt thanks to Jenny and Scott! They are great people. I can’t say enough good. Thank you.

A Spruce Cottage
I had a pleasant stay; I recommend this location.

Peaceful retreat for adventure seakers
Tina’s place was a 5 star oasis. The place was very clean and peaceful. She had everything that we needed there. We did not have any issues. We would definitely recommend.
Quick stats about guest house rentals in Winston-Salem
Total rentals
10 properties
Nightly prices starting at
£53 before taxes and fees
Total number of reviews
1.8K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- North Carolina Zoo
- Hanging Rock State Park
- Greensboro Science Center
- Wet'n Wild Emerald Pointe Water Park
- Sedgefield Country Club
- Pilot Mountain State Park
- Stone Mountain State Park
- Old Beau Resort & Golf Club
- Starmount Forest Country Club
- High Meadows Golf & Country Club
- Old Town Club
- Roaring Gap Club
- Divine Llama Vineyards
- Mooresville Golf Course
- Dan Nicholas Park
- Gillespie Golf Course
- Lazy 5 Ranch
- Lake Norman State Park
- International Civil Rights Center & Museum
- Olde Homeplace Golf Club
- Meadowlands Golf Club