Guesthouse vacation rentals in Kendall County

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Top-rated guesthouse rentals in Kendall County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Comfort

4.96 out of 5 average rating, 135 reviews

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!

May 20 – 27

€ 133 per night

Guest favorite

Guesthouse in Boerne

4.96 out of 5 average rating, 82 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

Apr 17 – 24

€ 120 per night

Guest favorite

Guesthouse in Boerne

4.98 out of 5 average rating, 434 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

Aug 31 – Sep 7

€ 93 per night

Guest favorite

Guesthouse in Boerne

4.96 out of 5 average rating, 25 reviews

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

Dec 14 – 21

€ 205 per night

Guest favorite

Guesthouse in Kendall County

5.0 out of 5 average rating, 148 reviews

Whimsy Hill Treetop Retreat w/ Hill Country Views

The Whimsy Hill Treetop Retreat is a quaint single bedroom upstairs apartment located in the countryside of the beautiful Hill Country. Completely renovated, and positioned high among the trees, this cottage has all the amenities and comfort you would want for your hill country visit. Sit on the front deck or covered downstairs patio and enjoy miles of amazing Texas Hill Country views. Hang out and take a plunge in the resort style swimming hole with waterfall or enjoy a soak in the hot tub.

Nov 20 – 27

€ 163 per night

Guest favorite

Guesthouse in Boerne

4.93 out of 5 average rating, 276 reviews

Country Guest House minutes from Downtown Boerne

2 bedroom/2 bath guesthouse just minutes from downtown Boerne. Large game room with pool table and movie projector 120” screen with amazing surround sound and a 65”LCD. Step out to the firepit and huge pool, shared only between the two guesthouses. New small kitchen with all new appliances. We welcome pets with a $20 pet pet feeNO PITBULLS AND ONLY 1 LARGE DOG Unsupervised pets must be crated. Just added relaxing water feature, new pool volleyball net and basketball hoop Super fast wifi

Sep 12 – 19

€ 200 per night

Guest favorite

Guesthouse in Boerne

4.97 out of 5 average rating, 65 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.

Oct 5 – 12

€ 100 per night

Superhost

Guesthouse in Pipe Creek

4.77 out of 5 average rating, 98 reviews

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.

Jun 14 – 21

€ 78 per night

Guest favorite

Guesthouse in Boerne

4.97 out of 5 average rating, 74 reviews

"Super Clean and Beautiful" our Entire 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.

Oct 3 – 10

€ 142 per night

Guest favorite

Guesthouse in Fair Oaks Ranch

5.0 out of 5 average rating, 39 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 allowed inside.

Jul 30 – Aug 6

€ 186 per night

Guest favorite

Guesthouse in Blanco

5.0 out of 5 average rating, 14 reviews

The Cottage

Relax and unwind at La Casita. Perfectly tucked into the bustling little town of Blanco, ours is a great place to rest after a day of exploring and experiencing all the cool things that make our home town so special. La Casita is a fun single bedroom little guesthouse, and has its own parking with a car port for cars or to just sit in the shade. A newly installed privacy fence gives privacy for a backyard BBQ or just relaxing in the evening. We can't wait to have you stay!

Jan 20 – 27

€ 90 per night

Guest favorite

Guesthouse in Boerne

4.96 out of 5 average rating, 435 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!

Jul 15 – 22

€ 96 per night