Holiday rentals in Henly

An aerial view showcases a spacious hill country retreat surrounded by lush greenery and a seasonal creek. A modern house with a metal roof is positioned near the water, with a walk bridge connecting the property to the opposite bank.

4.99 out of 5 average rating, 78 reviews

Private Ranch: Creek+Nature+ Gameroom+Relax

Relax & unwind on your own private 27 acre hill country retreat 10 mins from Dripping Springs. Admire sunsets from a rocking chair lined porch. Take the stairs down to the seasonal creek for a dip or head over to the bridge to look for birds, sunbathin' turtles, fish or a flock of turkey. Kick back & play a round of pool, foosball, arcade games or corn hole. Have drinks in the string-lit cedar room or sit on the screened-in porch & enjoy the sounds of nature. Stargaze & enjoy the dark night sky!

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, 275 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, 252 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

4.96 out of 5 average rating, 169 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!

Cabin in Dripping Springs

An inviting cabin interior features wooden walls and rustic decor. A spacious bed is accompanied by a cozy sitting area with leather sofas. A ping-pong table and a game area with a checkerboard are visible, enhancing the recreational atmosphere of the living space.

4.98 out of 5 average rating, 185 reviews

Backwoods BNB in Dripping Springs TX on 23 acres

Located in the Heart of the Hill Country just 10 miles west of Dripping Springs providing an easy day trip to many local favorites like Austin, San Antonio, Fredericksburg, & Wimberley. The cabin has 3 beds, living, kitchen, dining, bathroom & shower. The property has wildlife galore giving the feel of backwoods just 10 mins from civilization. Community pool available to guests 2 hours/day during the hours of 10A-3P with advanced reservation. Rules & use waiver must be signed in advance.

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, 112 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.

4.98 out of 5 average rating, 182 reviews

The interior of the Yurt showcases a spacious layout with a circular skylight dome at the center. A king-sized bed is adorned with colorful pillows, complemented by a cozy full-sized couch and a coffee table. Bright windows allow natural light to enhance the room's inviting design.

Yurt in Dripping Springs

Romantic Yurt Getaway: Private Hot Tub | King Bed

This one-of-a-kind Yurt in the Live Oak trees is your PERFECT getaway from city life! Located in the heart of Texas winery/brewery country, your day trips are only minutes away! This one bedroom (king) is hosted by Airbnb's 2022 Top New Host of the State of Texas! Relax in the private hot tub, stargaze, or sit around the fire on a 300+sq/ft deck surrounded by ancient live oak trees! The Hidden Oak Yurt is tucked away on a beautiful 9-acre property and offers all your modern amenities!

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.

4.93 out of 5 average rating, 130 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.

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. 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 just 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.

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.

4.91 out of 5 average rating, 169 reviews

Ranch House Retreat

The McBride Ranch is a family owned property nestled on 17 acres of wildlife habitat in the Texas Hill Country, between Dripping Springs and Blanco. The house has 3 bedrooms, 2 baths, living, dining, kitchen, sun room, covered deck, fenced yard and native butterfly gardens. The home set up is great for visiting and entertaining or just relaxing. It is close to wineries, distilleries, breweries, wedding & events venues, State parks and swimming holes.

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.

4.92 out of 5 average rating, 248 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. Enjoy sitting on the porch or at the picnic table under the trees to kick back and relax on a cool evening.

The exterior of a contemporary cottage is featured, showcasing a yellow facade complemented by stone accents and dark window frames. A large tree provides shade in the front yard, while a small patio area includes outdoor seating, surrounded by lush green landscaping.