Guesthouse vacation rentals in Kendall County

An outdoor area is defined by a stone patio surrounded by mature trees. A barbecue grill stands beside a seating arrangement of wooden chairs. String lights are hung above, and a hammock can be seen resting between trees, offering a cozy retreat in a spacious grassy setting.

4.95 out of 5 average rating, 109 reviews

Adorable 1-bedroom guesthouse on gated property!

Relax in this stylish space located 9 miles from Six Flags, 6.6 miles to Camp Bullis, 10 miles to Shops at La Cantera and The Rim. If Wineries are on the agenda, Fredericksburg is a skip down the I-10. Conveniently located close to I-10 for trips to downtown San Antonio or Historic heart of Boerne. After a full day of adventures, return to a peaceful 900 SqFt 1-bedroom to unload by the fire pit in the Hill Country. Lackland AFB is a short 34 miles away with 1604 and 410 a short drive on I-10

4.96 out of 5 average rating, 156 reviews

A view from the porch captures a vast landscape featuring rolling hills dotted with trees and greenery. The horizon stretches into the distance under a clear blue sky. A small wooden table is positioned in the foreground, accompanied by two chairs, creating a serene outdoor seating area.

Guesthouse in Comfort

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 rustic living area features two sleek leather chairs facing a small table. A wood-burning stove provides warmth, while soft lighting illuminates the space. A large map is displayed on the wall, and a cozy bed is partially visible in the background.

4.98 out of 5 average rating, 500 reviews

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

A quaint cottage is framed by a wood fence and a gravel pathway. The entrance features two white double doors, and a small seating area with red Adirondack chairs is visible nearby, inviting outdoor relaxation amid a natural setting.

4.95 out of 5 average rating, 77 reviews

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.

An open-concept kitchen and living area is displayed, featuring modern appliances and a dining table with metal chairs. A comfortable seating arrangement with light brown tones is positioned near large windows, allowing natural light to brighten the space. Neutral colors contribute to a welcoming environment.

4.97 out of 5 average rating, 101 reviews

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.

The entrance is framed by a large tree, with a stone pathway leading to the door. Two green rocking chairs are positioned on a covered porch, complementing a decorative star on the wall. Lush green grass surrounds the area, contributing to a tranquil outdoor setting.

5 out of 5 average rating, 50 reviews

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.

Guesthouse in Fair Oaks Ranch

A charming guesthouse structure is presented, featuring a spacious front porch with a ceiling fan. Large windows allow natural light to flood the interior. A gravel driveway leads to the entrance, surrounded by landscaping that includes small plants and stone accents.

4.98 out of 5 average rating, 59 reviews

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

The front exterior of the guest house features a welcoming porch supported by wooden posts. A star emblem adorns the center of the gabled roof. Two large windows flank the entrance, with rock details and potted plants adding to the natural setting.

4.97 out of 5 average rating, 171 reviews

Boerne Ranch Style guesthouse

Country guest house, located 4 miles from Downtown Boerne with easy access to San Antonio and surrounding hill country. Built in 2020, 2 spacious bedrooms, granite kitchen with a huge island and an open concept floor plan. Enjoy a 75" 4k tv with all streaming channels or relax on the front porch. Perfect for a weekend or extended stay. Step outside to the firepit or swim in huge pool with lots of shaded seating and tables, shared only between the 2 guesthouses.

5 out of 5 average rating, 37 reviews

A welcoming entrance is defined by a vibrant orange door and large arched windows. Planters with greenery and decorative baskets line the porch, which features wooden steps leading up and a textured rug on the floor, creating an inviting atmosphere.

Guesthouse in Blanco

Little Luxe Off The Square

Enjoy a little luxury right off the town square in one of the most historical homes in Blanco. Redone with a lot of cozy and a little swag in mind you'll definitely enjoy your stay in the middle of it all! This space with it's comfy king size bed is perfectly situated making the town of Blanco and any hill country destinations convenient all while enjoying Texas wildlife grazing right off your private porch and sunroom.

The exterior of the property is framed by lush greenery, featuring a stone pathway leading to a light-colored house with a gray roof. The two garage doors are visible, surrounded by native plants and trees, creating a natural and inviting setting.

4.96 out of 5 average rating, 473 reviews

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!

4.88 out of 5 average rating, 148 reviews

A tranquil river scene is depicted, showcasing clear water reflecting greenery along its banks. A person stands in the shallow water, wearing a wide-brimmed hat, while surrounding foliage creates a serene environment. Soft light filters through the trees, enhancing the peacefulness of the setting.

Guesthouse in Blanco

Texastopia Farm Guesthouse

VIEWS! Quiet and private. Great for couples or small families. Please make booking with at least 24 hours in advance. Thank you. *New Water System * New Floor* See Reviews Only 10 minutes driving from Luckenbach, 20 minutes to Blanco, & 25 minutes from Fredericksburg. Our guest house overlooks the beautiful Blanco River, and there is plenty of nearby recreation in this scenic area of the Texas Hill Country.