
Holiday houses in Gillespie County
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Top-rated holiday rentals in Gillespie County
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Around the Bend Bungalow
Craving a getaway with family or friends for wine tasting, great food and gift shopping? Want to enjoy their company, but unwind in your own space? Around the Bend Bungalow and Airstream Alfresco are located approx 12 minutes from Main St. with its abundant eateries and unique shops or 10 minutes from breathtaking views on Enchanted Rock. End your evening in a rocking chair admiring the endless stars. Longhorns wander our pastures and you share the location with an abundance of wildlife!

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!

1800’sLogCabin-PrivateRanch-KingBed-CopperBathtub
Rest easy at this luxurious and unique historic 1850’s log cabin. Minutes from Willow City Loop & Enchanted Rock. This comfy cabin is quiet, and peaceful. Historical Fredericksburg is a scenic 20 minute drive and after a day of wine tours, shopping or hiking, the cabins’ 66” Copper Tub will be waiting for a relaxing bath. Nature awaits behind the private security gates for taking a leisurely walk on the half mile “driveway” or venture out on country roads and enjoy the wildlife.

ROAM -Rooftop Hot tub/Close to Main&290 Wine/Views
ROAM is a beautiful home constructed of two repurposed shipping containers complete with nearly 1000 sq ft of deck area, great views, micro cows, and rooftop hot tub! This is the perfect place for your vacation, located right on the 290 wine trail and just outside of Fredericksburg city limits - a short drive to downtown . Spend a unforgettable holiday in the enchanting surroundings of the town of Fredericksburg, the perfect place if you like small town charm and hospitality.

Leaf Treehouse at The Meadow
The Leaf Treehouse (~300sqft) is perched among sturdy live oaks on our slice of Texas heaven just ten minutes from Main Street Fredericksburg. Its cozy and stylish interior includes a king bed with organic cotton sheets, a thoughtfully stocked kitchenette, a full bathroom with a rain shower, a padded reading nook with a round window, and an outdoor bathtub on the upper deck. Private propane grill below. If you don't see your dates, see the other treehouses on my host profile!

Boho Vibes in the Hill Country
Here’s the RUNDOWN: - QUICK DRIVE to MAIN ST - 2 parking spots RIGHT OUTSIDE - Sleepy-time = Chill time - Bedroom w/ KING Serta i-Series mattress & 55"TV - Spacious living w/ 4K 70"TV, ATARI Console & KING pullout - Sign in to YOUR STREAMING services! - Grassy Indoor Nook w/ hammock (chill out!) - 2 private patio spaces (yes two!) w/ gas FIRE PIT - Dartboard & games - COTTON bedding - NEW SINGLE-LEVEL condo - EQUIPPED kitchen - Dining + bistro table, dual as office & island!

Stunning Villa w/ Alpaca, Sheep, Donkeys, Hot Tub
Spotted Sheep Farms is located on 8 private acres and features two separate properties. The Villa at Spotted Sheep Farms, an Italian style 1,800 square foot home with beautiful finishes and a luxurious huge master suite. The property is home to animals and wild life including alpacas, miniature donkeys, and of course, spotted sheep! It’s perfect for a getaway, relaxing, enjoying some of Texas' best wineries, Fredericksburg shopping and the quiet evening in the hot tub.

DarkSkies Hideaway romantic getaway hot tub/fp
Welcome to Dark Skies Hideaway! An adorable guest house with amazing views! Take it easy in a unique and tranquil getaway. Not just a place to lay your head but an experience for all that enter. Enjoy the amazing sunrises and sunsets in a peaceful setting as you sit on your front porch. Lie in bed and look at the stars through the sky lights overhead. The dark skies allow you to see the milky way in all it's glory! This is paradise in the making!

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 ☀️

NEW | The Pedernales A-Frame
The Pedernales A-Frame epitomizes luxury... Nestled on an expansive 8-acres bordering the serene Pedernales River and positioned atop a tranquil hill, this cabin boasts sweeping vistas of the picturesque Texas Hill Country. Its interior exudes opulence with exceptional craftsmanship, acclaimed design, premium amenities, and a wealth of luxurious finishes that cater to even the most discerning tastes. We look forward to having you...

The Orange Cactus Casita | Peaceful, Country Views
Newly-built and ready to welcome guests, The Orange Cactus Casita is a private guest house situated on 10 acres of land. Sit back, relax and enjoy the views. This 2 bed, 2 bath guest house has everything you need including a full kitchen, living room and outdoor living space. This location offers the perfect opportunity for genuine relaxation in a countryside atmosphere, all within a quick 15-minute drive to Main Street.

Pecan Treehouse @ A-Frame Ranch
Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, the Pecan Cabin offers Hill Country views, stargazing, and deer sightings, yet you’re minutes from Main St. Swim in the container pool, gather at the fire pit, or simply unwind on your private balcony. Inside, enjoy a king bed, dual rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.
Popular amenities for Gillespie County holiday rentals
Other great holiday rentals in Gillespie County

Running Deer Lodge | A Fredericksburg Escape

Casa de la Paz - 26-Acre Wine Country Retreat

The Getaway at Do-Nothing Ranch

Casa StarLight Continental Suite

Dome 1 at Elevation Ranch

Sunsets & Starry Nights! 5 min to Main Festivities

Rośe Wine Barrel Cabin

Pecan Creek Cottage
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- Guadalupe River State Park
- Longhorn Cavern State Park
- Hidden Falls Adventure Park
- Texas Wine Collective
- Inks Lake State Park
- Hamilton Pool Preserve
- Pedernales Falls State Park
- Tapatio Springs Hill Country Golf Course
- Blanco State Park
- Escondido Golf & Lake Club
- National Museum of the Pacific War
- Fall Creek Vineyards, Tow
- Signor Vineyards
- Becker Vineyards
- William Chris Vineyards
- Inwood Estates Vineyards Winery & Bistro
- Hilmy Cellars - Vineyards, Winery & Tasting Room
- Kuhlman Cellars
- Ron Yates Wines
- Spicewood Vineyards
- Bending Branch Winery
- Slate Mill Wine Collective
- Grape Creek Vineyards
- Pedernales Cellars




