Vacation rentals in Henly

Cottage in Dripping Springs

A circle of dark green Adirondack chairs is arranged among trees, situated in a grassy area. The backdrop features a light-colored guest house partially visible, surrounded by greenery and garden elements, creating an inviting outdoor space for relaxation.

5.0 out of 5 average rating, 279 reviews

Star House Hill Country Getaway! Relaxation, Views

Welcome to the Star House getaway in Dripping Springs, known as The Gateway To The TX Hill Country within the Dark Sky Initiative & Wildlife Status. Your 38 acres boast scenic hilltops with amazing views of rolling ravines & views for miles. It’s an independent, elegantly appointed & eclectically furnished guest house surrounded by art, nature & gardens. Enjoy our harvested & filtered rainwater we call Cloud Juice! Pick organic vegetables & feed our sweet goats with goat nibbles left for you!

A modern farmhouse is depicted, featuring a spacious outdoor area with a clear swimming pool and a shaded seating area. A covered patio extends from the house, complemented by a grill and a few lounge chairs. Lush greenery surrounds the property, providing a serene backdrop.

4.97 out of 5 average rating, 100 reviews

NEW Chic, Luxury Home with Pool - Howard Ranch!

This unique + stylish modern farmhouse has you living in the lap of luxury! Breeze out of your designer bedroom (one of TWO primary suites!) into your gorgeous bathroom, then wander out to one of TWO decked out kitchens for coffee or tea, cook a few eggs from the chicken coop just on the other side of the driveway, then meander outside for a splash in the pool to stretch your legs or stroll the property on the walking trails! Close to wineries, wedding venues, and hill country beauty/adventures!

The cottage is illuminated against a night sky, highlighting its charming architecture. Soft lighting accentuates the inviting porch and stone detailing, while windows glow warmly from within, creating a welcoming entrance. Outdoor seating enhances the cozy atmosphere, perfect for relaxing under the stars.

4.99 out of 5 average rating, 254 reviews

Monticello Cottage

Monticello Cottage is situated on a hill, wide views, close to Dripping Springs, wineries, wedding venues, Blanco, Wimberley, Fredericksburg and Johnson City, Pedernales . The fresh air, comfortable beds, the coziness, the kitchen, the quiet, & night sounds, the fresh air and clear skies filled with stars at night. will delight you. Good for families, couples, great for brides and "pre-wedding weekends", artists and business travelers. EV charger available . Pet fee@ $60 per dog per stay

The charming white bungalow features two chairs placed on a gravel pathway, framed by a welcoming front porch. Large windows illuminate the interior, showcasing the inviting entrance door. A vibrant sunset sky enhances the serene outdoor setting surrounded by greenery.

4.92 out of 5 average rating, 179 reviews

Modern “Carmen”Farmhouse With Star Gazing Patio.

Discover our 1-bedroom suite on our 30 acre Madrona Ranch, surrounded by magnificent oak trees. Unwind on the inviting front porch or stargaze on the stone patio. This new suite features high-end finishes, including custom cabinets, vaulted ceilings, quartz counters, and maple hardwood floors. Enjoy country views and a starlit sky. Need more space? Inquire about our 2 additional bungalows and a 2-bedroom home on the property. Your escape awaits. 1 Exterior security camera faces the parking area

4.96 out of 5 average rating, 388 reviews

The interior of the yurt features a circular design with a skylight dome at the center, allowing natural light to fill the space. A spacious bed is positioned in the foreground, accompanied by a kitchenette and comfortable seating area in the background.

Yurt in Dripping Springs

Romantic Yurt Getaway: King Bed | Private Hot Tub

This one-of-a-kind Treehouse Yurt is your PERFECT getaway from city life! Located in the heart of Texas winery and brewery country, your day trips are only minutes away in every direction! This one bedroom (king bed) is hosted by Airbnb's 2022 Top New Host of the State of Texas! Relax in the spa, stargaze, or sit around the fire under a 300-year-old Live Oak Tree! The Tangled Oak Yurt is tucked away on a beautiful 9-acre property and offers all your modern amenities plus a king-size bed!

A modern two-story building is captured from an elevated view, showcasing large glass windows and sleek architectural lines. A spacious deck with seating overlooks the surrounding landscape, while trees frame the property, emphasizing its connection to nature.

4.89 out of 5 average rating, 119 reviews

2 units 1 price. Pickleball court. TX Hill Country

Hill Country pickleball. Listing is both units (2/2 and a 1/1) on 4 acres in the wedding capital of Texas. This hill country retreat has breath taking views. 10 minutes to Dripping Springs, 30 min. Wimberley and the Blanco river, 45 min. to Austin. Come explore everything Dripping Springs and the surrounding areas have to offer. Wineries and Breweries galore nearby. Family Friendly Dreamland 5 minutes away or just come for this beautiful home, view and the perfect central Texas getaway.

Villa in Dripping Springs

A spacious living area features large windows that provide expansive views of the Texas Hill Country. A comfortable sofa is positioned alongside a coffee table, while an open-concept kitchen with modern appliances is visible in the background, enhancing the bright and inviting atmosphere.

4.96 out of 5 average rating, 221 reviews

Luxury Villa | Pool | Views | Hot Tub | Fire Pit

Welcome to our Ranch. Located on 180 Acres in Dripping Springs, the Nook Villa is a Relaxing Luxury Modern Home with all the amenities you could possibly need. Decorated Mid-Century Modern and accented by beautifully restored antique pieces. This home is built around the west-facing picturesque 180-degree stunning views showcased throughout the indoor and outdoor spaces. Relax on the large comfortable sofa, the luxury hot tub, or on the covered porch to take in the beautiful sunsets.

Tiny home in Johnson City

A cozy living area is presented with a large light-colored sofa and an armchair. A wooden coffee table sits in front of the sofa, with a decorative cowhide rug underneath. A wall clock and a large television are mounted on a textured white-brick wall, enhancing the room's design.

4.98 out of 5 average rating, 263 reviews

The Green Casita at Caballo Creek

This tiny house offers luxurious Texas Hill Country accommodations which are easily accessible yet feel a world away from urban life. Enjoy the Casitas’ private refuge on 55 acres surrounded by hill country views with the comforts of an upscale hotel. The property is close to wineries, distilleries and breweries. The area is also well known for its abundance of parks and swimming holes including Pedernales Falls State Park (a 5 minute drive), Hamilton Pool, and Blanco State Park.

The exterior of a modern farmhouse is presented at dusk, showcasing large windows that illuminate the inviting interior. A covered carport provides sheltered entry. The surrounding yard is decorated with natural landscaping, and the atmosphere is enhanced by the soft glow of sunset hues in the sky.

4.99 out of 5 average rating, 120 reviews

Day Drippin' Farm-stay | Rainwater| New Build

Situated on one acre of fenced yard, our cozy retreat offers the perfect blend of Texas country charm and modern amenities. Built in 2023, our home features chemical-free rainwater collection, a whole-home propane back-up generator, and top-of-the-line appliances for your convenience. Check-in with your personal code on the keyless entry in the covered carport. We are a family owned business which means we oversee every turnover, and go the extra mile to welcome you.

Tiny home in Dripping Springs

A charming tiny home is featured, showcasing a welcoming front porch with a white railing. The entrance is accentuated by steps leading up to a central front door, framed by a gabled roof. Lush green grass surrounds the stone pathway, contributing to an inviting outdoor space.

4.96 out of 5 average rating, 52 reviews

Adorable Green tiny home-near Field of Dreams

Less than a mile from Field of Dreams & Speeding Springs. Super cute and sparkling clean! This little gem is so close to many of the main attractions in Dripping Springs and surrounding area. Less than 8 miles to Pedernalas state park. Perfect location if you’re looking for a quiet, beautiful, serene setting that’s close to everything you want but just far enough away to help you forget the big city. We hope you choose to come stay with us at Cricket Hill Ranch.

Farm stay in Dripping Springs

A welcoming living area features a comfortable sofa and an armchair, accented by soft lighting from a side table lamp. The kitchen area, equipped with modern appliances, showcases rustic shelving and a vintage hutch, adding character to the space. Natural light flows through the window.

4.92 out of 5 average rating, 134 reviews

Modern Cottage @ Flyin’ Arrow Ranch

Flyin’ Arrow Ranch is a special place for families to make memories. With open pastures, a park-like setting, plenty of massive old oak trees, and occasional events on the lawn, this little piece of the Texas Hill Country can be a perfect retreat for your family. Whether you’re staying in The Crooked Cottage and enjoying a spectacular modern farmhouse vibe or having a pop-up dinner party in the field, Flyin’ Arrow is a place for families to make memories.

A walkway leads to a charming house surrounded by a lush, green landscape. Mature trees provide shade over the entrance, while flower pots are arranged thoughtfully along the path, adding a touch of color to the natural setting.