Vacation rentals in Winedale

Luxe Farmhouse with Scenic Views and Cowboy Pool

Welcome to your private retreat in the heart of the Texas countryside - a modern farmhouse set on 18 peaceful acres, just minutes from downtown Fayetteville and 15 miles from the Round Top Antiques Fair. Designed with clean lines and subtle 1970s inspiration, the home features light-filled interiors and floor-to-ceiling windows framing panoramic views of rolling hills and endless skies. Ideal for star gazers, antique hunters, remote workers, nature lovers, or city dwellers needing to recharge.

King Beds | Luxury Farm Stay| 5 Min to Round Top

Modern Manor by Hill & Hollow Stays is a perfect home base for Round Top. Set on the sprawling Three Oaks Farm, this stylish modern farmhouse blends space, comfort, and thoughtful design for a perfect Round Top trip -Beautiful working farm with luxury interiors & furnishings -Cozy fireplace for relaxed evenings -Minutes to Round Top & Warrenton shows -Option to book the full estate (3 homes/pool) -Concierge services available We consider every detail to ensure an elevated, effortless stay!

Gypsy Farmhouse

The Gypsy Farmhouse is a 1952 Sears Kit House and the original farmhouse on the Junk Gypsy property. It features plush beds, custom Signature Hardware bath tubs, a gourmet kitchen and a large seating area with a rock fire place. There is a king bedroom downstairs with a custom crown headboard, tufted sofa & a full bath with a oversized copper bathtub. Upstairs there are 2 bedrooms with 2 queen beds in each room and a shared full size bath. Additionally, there is. 1/2 bath downstairs.

Pool, HotTub- Cardinal Cottage, RoundTop/Brenham

-Private home & large lap pool for your use during your stay. No other renters on the property. -Wide open outdoor spaces to get away. A breath of fresh air. See the stars at night! -GREAT WiFi signal. - 1600 sq ft home on 11 acres. Common areas downstairs, bedrooms upstairs. -Lap Pool (not heated) and spa hot tub (heated year round). Pool towels provided. -Firepit area. I provide firewood, fire starters, & lighter. -Brenham 10 minute drive. Round Top 20 minute drive. Sorry, no pets.

The Horseshoe Cottage

Charming Texas Hill Country guest cottage located on 19 acre private family horse farm. Easy access to Hwy. 237, close to Festival Hill and 2.5 miles to the town square. This spacious studio has a queen bed and day bed with trundle (two twin beds). There is also a kitchen with a small refrigerator, microwave, toaster oven and Keurig. The bathroom has a large walk in shower, washer/dryer and closet space. Air Conditioning, Heat. WiFi avaliable. Covered porch with two rocking chairs.

Azure Skye Haus (Guest House) - Round Top

Need a countryside getaway? There is no better place than Azure Skye Haus! Enjoy the private, quiet setting where you can experience a beautiful sunset on a vintage glider, breathe in the fresh air, and enjoy the sounds of the countryside in the heart of Round Top. A beautifully appointed 2 bdrm guest house with a fully equipped kitchen, coffee and teas provided, private bath, luxury linens and towels, full-size washer and dryer, and more. A private carport with extra parking.

The Union Hill House *Outdoor Hot Tub*

Discover the ultimate Texan getaway for family and friend groups alike at the Union Hill House! This Round Top-area compound offers 5 bedrooms and 5 full baths on 5 sprawling acres with an outdoor hot tub. Perfect for groups of up to 12, this property is just a short drive from Houston or Austin. Indulge in the chef's kitchen, cozy up by the outdoor fire, or take a walk in the lush green fields. The Union Hill House is the perfect escape. Book your stay today!

Camelia Farm Burton Little House

This 326 sq.' of comfort is small, but feels spacious once inside. There is a full kitchen so you can prepare whatever meals you want on a small scale, full bathroom, queen bed in private bedroom, separate living room and dining space. The sofa opens into a full size, comfortable bed. We are minutes from great restaurants, antiques, and fun. Close to Brenham, Roundtop, Carmine, Burton, Bellville, Fayetteville, Giddings and Lake Somerville state park.

Summer is here and it's awesome in Round Top

Come get away from the city craziness! Clean air, beautiful stars and having the house all to yourselves! There are two large bedrooms with a comfy king sized bed in each. The house is appointed with interesting art pieces and furniture. The porches welcome you to sit and sip and enjoy for hours the beautiful countryside in our small piece of heaven in Texas. Slowly but surely Texas will be open for business again!

The Old Farmhouse

At dawn, the sun rises and washes the horizon with a soft golden glow, coloring the sky with lively oranges and pinks. When evening arrives, it slips behind the trees, leaving brilliant, deep red hues that are truly breathtaking. After dark, countless stars appear, sparkling like diamonds on a rich, dark canvas, enriching the peaceful and magical mood of the area. Every moment spent here fills you with calmness and awe.

Round Top Designer Home

Escape to this professionally designed 3BR/2BA home on 16 private acres, just minutes from the Round Top show grounds. Ideal for show visitors, designers, or families, the home features a king master with en suite, a queen room, and a twin room with a shared Jack-and-Jill bath. Enjoy stylish interiors, peaceful surroundings, and easy access to all Round Top has to offer—your perfect Hill Country retreat awaits!

Ladies Lounge @ Carmine Compound

Stay in this adorable pink, western vintage–styled house just minutes from the heart of Round Top, Texas. Full of charm, cozy details, and Texas personality, this home is the perfect retreat for antiques shoppers, girls’ weekends, or a relaxing country escape. The space:     •  Primary bedroom: King bed + private bathroom     •  Second bedroom: Two twin beds + private bathroom, perfect for friends or family.