Holiday 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 out of 5 average rating, 260 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!

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, 238 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.

4.91 out of 5 average rating, 150 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

4.97 out of 5 average rating, 131 reviews

A cabin with a distinctive metal roof is nestled on a hillside, surrounded by lush greenery. The expansive view showcases rolling hills and valleys under a cloudy sky, creating a peaceful and natural setting.

Cabin in Wimberley

La Lomita Cabin - Amazing Views, Hot tub

Welcome to La Lomita, an intimate cabin retreat for two in Wimberley! Perched above the treetops, this charming cabin offers comfort and stunning hillside views. The thoughtfully designed interior blends rustic charm with modern style. Keep an eye out for the enchanting wildlife and a spectacular sunrise. The well-appointed kitchen and cozy living area complete this magical setting. Relax, rejuvenate, and reconnect with nature. Experience the magic of Wimberley from the best seat in the house!

4.98 out of 5 average rating, 666 reviews

The cabin is surrounded by lush trees, with a spacious deck offering outdoor seating. A rocky path leads to the entrance, and kayaks are visible on the side. Natural stone and greenery frame the area, creating a serene atmosphere in the Texas Hill Country.

Home in Wimberley

Salvation Cabin

Wimberley's #1 rated award-winning “Salvation Cabin" is in the beautiful Texas Hill County wilderness with outdoor exploration, hiking and a Blanco Valley porch view to observe birds, deer and other wildlife. A throw back to gentler times, you'll leave here touched by nature's healing power. Come and be restored. 500+ visitors testify this is a one of a kind place. Please note* the Hill Country area is in drought presently in 2025. Blanco River dry, but Cypress Falls Swimming Hole close by.

Tiny home in Dripping Springs

A cozy living space features a blue sofa with black and white cushions, a wooden coffee table, and a dining area with a table for four. Large glass doors provide natural light and open to a porch, while a sleek kitchenette is visible along the wall.

4.93 out of 5 average rating, 231 reviews

NEW! Wanda - modern house at Tom Dooley’s Hideout

Tom Dooley’s Hideout is located at the Gateway to the hill country, just minutes west of Dripping Springs off of hwy 290. It’s a unique 4 acre property with 5 modern tiny houses that sit on open range with free grazing livestock which occasionally show up as they do not belong to us. This tiny house comfortably sleeps 2 on a queen bed but we do have a sofa/futon thats great for kids. Enjoy sitting on the porch or at the picnic table under the trees to kick back and relax on a cool evening.

Superhost

An open living area features a leather sofa and a wooden coffee table with potted plants. Large windows allow natural light, while a dining space is visible in the background. The kitchen is equipped with stainless steel appliances and wooden cabinetry.

Tiny home in Dripping Springs

4.85 out of 5 average rating, 267 reviews

Brady Villa @ D6 Retreat: Hike/Swim/Yoga

The Brady Villa at D6 Retreat sleeps 4 and offers guests a rejuvenating escape. Surrounded by natural splendor, the cabin provides direct access to hiking trails, butterfly gardens, wet-weather creek, & amazing sunsets. Guests can also enjoy the retreat's infinity pool, gift market, cafe, yoga studio for classes & community fire pit where fellow travelers gather. This sacred space invites visitors to craft their own transformative getaway in the heart of the serene Texas Hill Country.

Villa in Dripping Springs

The spacious living area features large windows offering panoramic views of the Texas Hill Country. A comfortable sectional sofa faces the view, while a dining area with modern pendant lights is visible in the background. The warm wood flooring adds a natural element to the design.

4.98 out of 5 average rating, 192 reviews

Luxury Home - Stunning Views, Pool, Hot Tub

Welcome to our Ranch. Located on 180 Acres in Dripping Springs, the Hideaway House is a Relaxing Luxury Modern Home with all the amenities. Decorated Mid-Century Modern and accented by beautifully restored antique pieces. This home is built around the west-facing picturesque 180-degree views showcased throughout the indoor and outdoor spaces. Relax on the large comfortable sofa, pool, luxury hot tub, or on one of the multiple covered porches and gazebos to take in the beautiful sunsets.

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.

4.88 out of 5 average rating, 103 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.

Tiny home in Johnson City

A modern tiny house is depicted with a light blue exterior, featuring several large windows that allow natural light to fill the interior. A stone pathway leads to a covered front porch, offering views of the expansive green landscape and hills in the background.

4.98 out of 5 average rating, 263 reviews

The Blue Casita at Caballo Creek Ranch

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.

4.96 out of 5 average rating, 335 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

Breathtaking Treehouse Yurt-Romantic Getaway!

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 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!

The exterior showcases a charming blue farmhouse with a welcoming front porch. Two red chairs are placed on the porch, framed by flowering shrubs and a stone pathway. A wooden fence lines the front yard, enhancing the serene countryside atmosphere.