Guesthouse vacation rentals in Kendall County

Charming Hill Country Casita + Patio

Experience true Hill Country serenity with five-star comfort at this newly built casita, thoughtfully designed for guests who appreciate quality, privacy, and a beautiful natural setting. Set on a picturesque property where deer and local wildlife frequently wander by, this charming two-bedroom, two-bath retreat offers a peaceful countryside escape just 25 minutes from the shops, restaurants, and parks of Downtown Boerne. Inside, the casita feels refined yet welcoming, with a spotless, well-stocked kitchen featuring stainless steel appliances, cooking essentials, and everything needed to prepare meals with ease. Comfortable living spaces invite you to slow down and relax, whether you’re enjoying a meal at one of the dining tables, playing board games, reading a book, or unwinding in the evening with cable TV. Each bedroom offers a queen bed dressed for comfort, while the bathrooms provide spa-like touches, including a walk-in shower and a shower/tub combination. Central air conditioning and heating, ceiling fans, a washer and dryer, and quality linens and toiletries ensure a seamless, hotel-level stay. Step outside to enjoy the quiet beauty of the property, where an outdoor seating area overlooks the surrounding landscape, making mornings with coffee or evenings under the stars especially memorable. Nature lovers will appreciate being close to the Guadalupe River and the scenic Kreutzberg Canyon Natural Area, while day trips to San Antonio remain an easy option. The homeowner resides on the property, and an exterior security camera faces outward for added peace of mind, allowing you to enjoy your stay comfortably and confidently. This casita is ideal for couples, friends, or small families seeking a polished, tranquil retreat that blends five-star quality with the authentic charm of the Texas Hill Country. Guests with mobility issues will enjoy the step-free access as you enter the home, the grab bars located in the master shower and wider doorways throughout the home.

Dog Trot Guest Suites on the RW Ranch

Welcome to the hilltop on our 135 acre ranch. We are located in the heart of the Texas Hill Country with close proximity to everything! Our Dog Trot Guest Suites consists of 2 suites each with a queen bed, an additional sleeping area (daybed or trunnel) and private bath. Our 180 deg views are spectacular and the stars at night are big and bright! We are a short distance from Old Tunnel State Park, James Kiehl River Park, Sister Creek Winery, foodie restaurants and caves. Hope to see you soon!

The Sunday House

Welcome to the Sunday House! Our tiny home was built by hand using reclaimed materials with your rest & relaxation in mind. This rustic romantic getaway is equipped with many amenities including a queen-sized memory foam mattress, kitchenette, full size bathroom with a shower and a wood burning stove to keep you cozy. Enjoy a complementary cup of coffee in our courtyard garden or snuggle up inside for a movie. NO CLEANING FEES 2022 Permit #2200146 Photo Credit: Aubree Lorraine Photography

The Oak Haus ~ Hill Country escape

Welcome to the Oak Haus - your perfect Hill Country escape! 7 min from Boerne, 5 min from river access ~Cozy, remodeled guest house with full kitchen, washer/dryer, dedicated workspace and all the comforts of home ~Pet friendly with fenced in yard area ~Covered back porch with private hot tub, rocking chairs ~Separate game room w/ 6 arcade games, foosball, TV and seating ~Endless outdoor activities, BBQ grill, firepit, basketball court, cornhole, horseshoes, view Axis/Whitetail deer

Hill Country Cottage - Play, Relax, Explore!

Located in the heart of The Hill Country, Hill Country Cottage has all you need. It is 3 minutes from the Guadalupe River, within easy driving distance to many quaint towns and only 45 minutes from downtown San Antonio; or just enjoy the peace & quiet right here. Hill Country Cottage is a private cottage in a quiet neighborhood. Kitchenette has small refrigerator, two eye cooktop (no oven), microwave, toaster, Keurig coffee maker and teapot. Flat screen tv in living area with wifi, Roku.

Benita's Getaway in beautiful Texas Hill Country

Welcome to Benita's Getaway located off Highway 16 in Pipe Creek. This cozy guest house is situated behind the main house. Fully equipped kitchen- full size refrigerator, stove, toaster, coffee pot, blender. There is a lot to offer in the surrounding area: 10 mi. east is Medina Lake for fishing and boating; 13 mi. north to Bandera "Cowboy Capital of the World" for river tubing and horseback riding; 12 miles to Tapatito Springs for golf; and 19 mi. west to Boerne with it's unique shopping.

Wanna see some deer? Clean & Peaceful Guesthouse!

This beautiful newly built second story Guest House is just a 35 minute walk from The Hill Country Mile. A walkable stretch of locally-owned boutiques, antique shops, restaurants and galleries set in the heart of downtown Boerne, Texas. Enjoy the local shopping, fine dining, breweries, coffee shops, market days, events, a stroll along the river or just stay in and relax while you enjoy our private covered porch overlocking our beautiful quiet neighborhood with lots of majestic oak trees.

La Casita on the J

Want to get away from the hustle of everyday life? Enjoy a relaxing stay at La Casita on the J! This beautiful 1200 s/f guest cottage sits on 4 acres and boasts peace and quiet! The home has a private 600sq/ft wrap around partially covered deck with comfortable outdoor seating and bistro dining areas. We have abundant wildlife on the property and the birds and hummers entertain at the various feeders and baths! 7 minutes to Main Street and 13 minutes to Sisterdale wedding venues.

Hill Country getaway - 2BR guesthouse

Come and enjoy our centrally located, cozy, comfortable and quiet getaway just outside San Antonio! Guesthouse located on 5 acres, perfect retreat or base camp for exploring the hill country. Watch the deer, birds and other wildlife from the spacious deck! 2 pets welcome with a $50 pet fee - only 1 large (40+) dog allowed. Unsupervised pets must be crated. Please be sure to include your pet where guests are listed. 4 guest limit, up to 4 visitors allowed. No smoking - No fireworks

Boerne Ranch Style guesthouse

Modern country guest house just 4 miles from Downtown Boerne with easy access to San Antonio and the Hill Country. Built in 2020, it features 2 spacious bedrooms, a granite kitchen with a large island, and an open-concept layout. Relax with a 75” 4K TV or enjoy the front porch. Step outside to a large shared pool, shaded seating, and firepit—shared only with one other guesthouse. Perfect for a weekend getaway or extended stay.

Hill Country Carriage House

We have everything you need for a romantic getaway, business travel or fun family time. We live in a wonderful neighborhood where deer and chickens roam free. We are about a 5 minute drive to/from Main Street and in the very heart of the Texas Hill Country. Southern hospitality, hiking trails, wineries, brew haus, music venues and everything the great HC offers is here. Come be our guest! Read entire site for info!

Pleasant Valley Hideaway

Welcome to our charming 1-bedroom retreat, nestled on tranquil acreage with stunning sunsets and peaceful nights. Located in the picturesque town of Boerne, our getaway offers the perfect blend of small-town charm and modern comforts, with easy access to the vibrant downtown San Antonio, the scenic Fredericksburg and the many Texas state parks (Guadalupe River State Park is 12-minutes away).