House holiday rentals in Gillespie County

The modern farmhouse features a gray exterior and a metal roof, complemented by a spacious front deck and a landscaped yard. Large windows provide a view of the interior living area, while majestic oak trees add natural shade to the surroundings.

4.99 out of 5 average rating, 180 reviews

Farmhouse Hot Tub & Fireplace Min to Town/Wineries

Treat yourself to an unforgettable weekend at this fully remodeled modern, rustic 2/2 farmhouse. Situated in the heart of wine country, you will find this peaceful haven 3 mins from town. Relax in the hot tub in front of the custom fireplace or sip wine on one of the decks that sit under large, majestic Oaks. Inside, be immersed in the stunningly finished interior with a serene and sophisticated feel. Stocked with everything you need. You'll enjoy every aspect of this stress-free home. Cheers!

A shared courtyard area features distinctive black and white checkered flooring, two hanging chairs, and colorful accent pillows on a sofa. Sunlight illuminates the space, highlighting the brick walls and wooden beams overhead. A small table is positioned between the chairs for added comfort.

4.92 out of 5 average rating, 325 reviews

Insta worthy boho house close 2 main & wineries

Kick back and relax in this calm, stylish space. 2 bedroom 2 bath house located a mile from Main St- shopping, food & wine. Big shared courtyard space w/private front & back patios to sit out on & enjoy your morning coffee w/the sunrise or glass of wine while watching the big Texas sunset. Master has a king bed & attached master bath w/white soft robes for your enjoyment. Second bedroom has a queen bed & access to 2nd bathroom in hallway. 1 living area equipped with TV. Fully equipped kitchen

An outdoor space is showcased, featuring a wooden deck with a hot tub and various seating arrangements. A circular fire pit is positioned on the lawn, surrounded by several chairs. A large umbrella provides shade to a dining table, while a fence frames the yard.

4.98 out of 5 average rating, 178 reviews

MidCentury Charm|Hot Tub|Firepit|Pets|Walk to Main

Gather with family and friends! Updated 3 king beds/2 baths/2 blocks off Main on corner lot. In the evening, enjoy the hot tub in fenced pet-friendly oversized yard, have wine by the fire pit as the deer emerge from banks of Town Creek, or enjoy a game of ping pong/corn hole. The home features soaring ceiling/open-concept design perfect for meals/games. Kitchen has new appliances and large sit around bar. Patio offers gas and charcoal grills. Make MEMORIES at Bowie-N-Travis! Permit #8056001607

A charming bungalow is presented with a well-maintained garden and a welcoming pathway leading to the entrance. The white exterior is complemented by gray shutters and a vibrant red door, framed by seasonal flowers and greenery.

4.99 out of 5 average rating, 279 reviews

Sunny cottage + clubhouse, hot tub, blocks to Main

Newly renovated 1940s bright & cozy bungalow featuring hot tub, clubhouse & fire pit! Just 6 blocks from the action on Main St! Three luxurious bedrooms; primary room with a king and ensuite bath, 2nd room with a king & 3rd room with a queen, 2nd full bath, fully equipped kitchen, gourmet coffee bar, beautiful living room with comfy sectional, fun, private 'Clubhouse' with games and big screen TV, patio, pergola with dining, grill and fire pit! Soak away the stress in our hot tub! #8056001013

A spacious master bedroom features a wooden four-poster bed with a cozy blanket. A stone fireplace stands against the wall, complemented by a framed landscape painting. A simple wooden chair adds to the serene atmosphere, while natural light enters from an adjacent doorway.

4.99 out of 5 average rating, 219 reviews

Cozy Cottage | Block off Main | Sauna & Hot Tub

The German Cottage of your dreams! Enjoy a modern twist on a classic cottage one block off of Main Street with a surprise inside- a HIDDEN speak easy! Guests solve a 5 part riddle to find the code that unlocks the wardrobe door to “Narnia”! To find out how to access the speakeasy, you’ll embark on a short riddle experience through the home, leading you to unlocking the Narnia wardrobe! Step through & Inside you’ll find the rustic speakeasy with a Hill Country prize waiting for you inside!

A welcoming living area is presented with a spacious brown sofa facing a mounted flat-screen television. Large windows draped with black curtains allow natural light to enhance the greenery from potted plants. A sliding door provides access to an outdoor space, contributing to the airy feel.

4.98 out of 5 average rating, 250 reviews

Beasts

This cozy condo is just minutes from downtown Fredericksburg, easily accessible to restaurants, winery's, shops, fun music venues and local breweries! It is the perfect getaway for couples or fun with friends! Relax on the patio, gaze at the stars, and enjoy a drink by the fire. This space was inspired by Austin's live music scene. Be inspired to write, play, be creative and have fun on the piano or guitar. This condo is retreat from our busy lives, so relax and enjoy your stay at Bestos!

A rustic rock cottage is surrounded by green grass and trees, with a picket fence lining the property. A small outdoor seating area is visible, including chairs and a table. A birdbath is set in the garden, enhancing the serene outdoor environment.

5 out of 5 average rating, 135 reviews

Cottage near Fredericksburg

Relax at my unique tranquil rock cottage less than 2 miles to Main Street on the edge of town surrounded by oak trees and adjacent to peach and pecan orchards. Enjoy the sunrise on the front porch or the sunset on the back porch while relaxing to the sights and sounds of nature. Take a step back in time and enjoy relics of the past in my cottage. Sunrise Grove Cottage is best suited for a couple seeking a quiet place to stay while visiting our lovely hamlet. Man spricht deutsch.

The exterior features a charming farmhouse with a covered porch and decorative railing. A stone pathway leads to the front door, surrounded by a meticulously landscaped yard with low shrubs and gravel. The home includes large windows and a metal roof, creating an inviting appearance.

4.96 out of 5 average rating, 331 reviews

2 Blocks to Main! Luxurious Farmhouse w/Fire-pit

Escape to Laurel Haus, a beautifully renovated vacation rental just two blocks from downtown Main Street in Fredericksburg, Texas. This renovated house offers modern luxury and charm. The spacious home sleeps 6 in 2 bedrooms + a Loft—two king suites and two twins—and has 2 full bathrooms. Relax on the patio, gather around the fire pit, or unwind after exploring Fredericksburg’s wineries, shops, and Texas Hill Country. Book now for a memorable wine country retreat in Fredericksburg!

An outdoor deck features a glimpse of a plunge pool surrounded by natural scenery. Two lounging chairs are positioned next to a small dining table. The sky displays soft pastel hues during sunset, enhancing the tranquil setting of the area.

5 out of 5 average rating, 247 reviews

Luxury+Privacy+Pool+Near Town

Escape the hustle to this Guest House located on 15 private acres just a 5 minute drive to town in an exclusive gated subdivision. You'll love the tranquil setting and privacy all while being a short drive to Main Street. We hope this will be a restful and restorative place for couples to enjoy quality time together in a romantic setting or for someone to enjoy a quiet retreat alone in a peaceful setting. Follow us @revivalridge on IG ☀️

A modern living area features a cozy gray sofa adorned with decorative cushions. A dark coffee table sits on a patterned rug, complemented by stylish pendant lighting above. The open layout highlights the adjoining kitchen with sleek appliances and a warm wooden floor extending throughout the space.

4.94 out of 5 average rating, 182 reviews

Tempranillo Haus- Hot Tub Getaway Near Main St!

Whether you seek a romantic getaway or a rejuvenating escape to wine country, Tempranillo Haus is equipped with everything you need for an unforgettable experience. The fusion of boho modern aesthetics, romantic ambiance, and the allure of a private hot tub converge to create an oasis of relaxation. Located in the hear of Fredericksburg and only minutes to downtown where shopping, wine tasting, and delicious restaurants awaits you.

A comfortable bedroom features a wooden sleigh bed with crisp white linens. Natural light brightens the space through a large window, complemented by sheer curtains. Decorative wall art enhances the ambiance, while a small bedside table provides convenient lighting options.

4.94 out of 5 average rating, 1,016 reviews

Tiled Shower, Walk to Main, Kitchenette, Smart TV

Master bedroom suite with private entrance. Two blocks from Main and War Museum, Otto's. Great location to explore FBG on foot. Private little entrance area with a 380 SF room. Shared walls (insulated) with one other full BNB apartment and my house. Extra-long soaking tub, large walk-in shower, a traditional wall shower, and a rain head. Off-street parking and fire pit in the front. Check out Casa Tranquila for more space! STR23-0550

The Aframe cabin features a modern design with large glass windows, allowing for natural light to fill the interior. A spacious deck is accessible via a set of stairs and is furnished with lounge chairs, providing a comfortable outdoor area for relaxation.