Holiday rentals with a patio in Winston-Salem

The Colonial Winston-Salem: a boutique guest suite

A beautifully decorated basement suite 15 minutes from downtown Winston, near Lewisville and some of the best wineries! The space is entirely yours, complete with a charming patio, kitchenette, full bathroom, and studio bedroom/living room. Sit out on the patio with a cup of coffee from our fully stocked coffee bar and watch the deer & birds, or grab a book and snuggle in cozy bedding. We are an active family with dogs & kids living upstairs, so we've provided everything you need for quiet!

K-Obscura, Romantic Downtown loft

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 complimentary coffee and treat at Krankies. Quiet for a downtown spot with the exception of an occasional train passing through adjacent lot. Includes deep soaking tub, mini-kitchen and comfy king size bed. Space is accessed via stairs. Parking included.

Comfort & Convenience in this 3BR Brick Ranch

Your family will be close to everything when you stay at this centrally-located place. The following destinations are only 5 minutes away:  Wake Forest Baptist Medical Center; Main Street, Winston Salem and the Stevens Center as well as the Dash Baseball Field (Truist Stadium).  You can sit on the back sunroom porch & listen to the baseball games or the birds.  Shopping galore & lots of restaurants are also close.  Washington Park is right behind the house.  Ride your bikes & walk the greenway.

Cozy King Blue H2O Staycation , Pool & Hot Tub

Quiet secluded STAYCATION w/ Fully Fenced Back Yard for the PUPS. We have a hot tub for year round use and a Stock Tank Pool (Closed until 5/23/25) . A fire pit to unwind. Back yard BBQ with a built in bar top table and a cozy Sectional to enjoy the outdoors. Inside we have an amazing plush King size mattress to take all stress away. Full kitchen * Hot tub - I will do my best to have it available at all times unless there is a mechanical issue. (No refunds if hot tub is not available)

The Morning Star Lofts

Welcome to your home away from home in Winston-Salem! Nestled on the peaceful hills of Winston-Salem, this comfortable 2-bedroom, 2-full bath apartment offers a perfect blend of relaxation and convenience. Ideal for families, couples, business travelers, or traveling nurses, our space provides everything you need for a memorable stay. Our apartment is located in a quiet, friendly neighborhood but is just a short drive to local attractions (~12 mins from Wake Forest, Costco, and Downtown).

West End Wonder! Rooftop Deck, Walk Downtown, 2 QN

Take in the West End neighborhood views from our private rooftop deck! Once you’re settled in, stroll down to some of the best restaurants & shops in downtown. Guests will enjoy our newly renovated apartment which is equipped with high speed WiFi, quality mattresses & linens, smart tv, fully equipped kitchen, & more. We offer a complimentary coffee/tea station & toiletries. Shared washer/dryer on site. Traveling with a group? Our property has 3 units that can be booked individually!

The Dragonfly in Buena Vista (near BMH & WFU)

Naturally lit, spacious 800 sq ft basement apt, 1 bdrm / 1 ba, located in the premiere Buena Vista neighborhood. Centrally located, only minutes away from downtown, WFU, and Baptist Hospital. Sidewalks and azalea-laden landscapes abound in this 1920's era neighborhood. Two bicycles give you alternative means for exploring. All rooms have natural light. Bedroom has two twins pulled together (with a bridge) to make a comfortable king. A rollaway bed is available on request.

House in Sunnyside W-S w/NC Beer Tasting!

Absolutely NO Parties or large gatherings allowed. You will be kicked out. Only guest registered are allowed to stay. You and your family will enjoy this spacious 3 bedroom home which is located in the historic Sunnyside area of town! Located a little over 1 mile into the downtown area, you will have easy access to nightlife, tourist attractions and lots of great food options! If you are a beer fan, I own Hoots Beer Co. and offer a free tour and tasting with your stay, so just ask!

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.