
Family-friendly holiday rentals in Gillespie County
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Top-rated family-friendly rentals in Gillespie County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Cozy 2 bed log cabin in natural setting.
Private cabin in the heart of the Hill Country. Built by our father in his early twenties, its known by long time guests as John's Cabin. We wanted to share this property and all its magic with anyone who genuinely appreciates the outdoors. So please enjoy a stay in a natural setting with a catch and release fishing pond, indoor/ outdoor fireplace, and all the quiet one can ask for. Sip your morning coffee to the sounds of wildlife just a few minutes away from downtown Fredericksburg.

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.

Grand Oaks Ranch · Pool·Spa · Game Barn · Animals
Built beginning in 1848 and over several generations, Grand Oaks Ranch is a historic limestone farmhouse sleeping 16 on 22 private Hill Country acre with a resort pool, hot tub, fire pit, and barn. Unwind poolside, sip wine at sunset, roast s'mores under the stars, or challenge your crew to a late-night ping pong battle in the barn. Friendly cows, goats, and horses roam the property. Minutes from Main Street and the wineries. Authentic Texas ranch life with every comfort you'd want.

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!

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!

Romantic A-frame with Private Hot Tub
Romantic A-frame cabin on a quiet Hill Country ranch, just 10 miles from Fredericksburg Main Street. Soak in your private hot tub, relax on the covered deck with ranch and wildlife views, and spend your days exploring wineries, breweries, shops, and Enchanted Rock. Designed for two, this secluded cabin gives you the quiet of the country without being far from town. Perfect for anniversaries, wine weekends, birthdays, proposals, mini-moons, and quiet couple getaways.

Hill Country A-Frame Cabin | Pool, Sauna & Nature
🌄 Modern A-Frame cabin on 17 scenic acres near Fredericksburg 🛏️ Sleeps up to 9 with 3 bedrooms + loft + sofa bed 🌿 Private patio with grill, fire pit & stock tank pool (heated option) 🧖 Access to shared cedar sauna on-site ☕ Fully equipped kitchen with local Hill Country coffee 🚗 Easy self check-in & on-site parking 💕 Family-friendly with loft hangout 🌌 Incredible stargazing in a Dark Sky Community 🦌 Peaceful Hill Country setting minutes from Main Street

Riddle Haus| Block off Main| Sauna| XL Hot Tub
Welcome to The historic, German homestead of your dreams, a block off of main street! Enjoy the most unique experience of Fredericksburg! This newly restored homestead comes with the ultimate surprise- a HIDDEN wine cellar! To find out how to access the cellar, you’ll embark on a short riddle experience through the home, leading you to the secret access point! Inside you’ll find the perfectly preserved wine cellar with a Hill Country prize waiting for you inside!

Casita Azul PRIVATE STUDIO 5 Min Drive to Downtown
Beautiful newly built studio style Casita. Enjoy the peace & quite of the Texas Hill Country while being just a few miles away from downtown Fredericksburg. The Casita is equipped with WiFi and a Smart Tv. We also provide a coffee bar set up for your enjoyment as well as an outdoor area with a fire pit and seating. Bbq pits are on the property so bring some steaks to grill and your favorite bottle of wine to dine under the stars! We hope to see you soon

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.

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.

Cute Farmhouse w/ donkey, sheep & hot tub! WINE
The Farmhouse at Spotted Sheep Farms is a Texas chic property and is perfect for a wine country getaway. The property is home to animals and wild life including, miniature donkeys and sheep! It boasts an open floorplan with full kitchen, queen bedroom, loft with two twin beds, brand new HotTub, satellite TV, WiFi, Netflix, outdoor games, fire pit, and large porch to watch the sunset and farm animals.
Popular amenities for Gillespie County family-friendly rentals
Family-friendly home rentals with a hot tub

The Arroyo at Meridian, Hot tub & Firepit!

Kaye Haus: Gorgeous home w/ hot tub!

Das Grun Haus With Private Hot Tub!

Close to Main- Pool, Hot Tub, Family Friendly

Romantic Cottage with Hot Tub in Fredericksburg

Fredericksburg 3BR•Pool•Hot Tub• Wine Trail• Pets

6 BR Hill Country Farmhouse Estate w/Hot Tub&Games

Acres Near Main- Game Saloon, Hot Tub, Dog Welcome
Family- and pet-friendly home rentals

Airstream Glamping Near Town!

Fox Burrow/acreage horse/u must query for pet/pets

FlyingCloud Airstream

Charming and updated home one block from Main St.

Luxury Tree House X Magical Romantic Forest! Pool!

The Gumbo Getaway on CherryMountain/Pets stay FREE

Historic Cabin +Working Sheep Ranch

Around the Bend Bungalow
Family-friendly home rentals with a pool

Conestoga "Glamping" Wagons

Big Red Bunk Haus, 8 BR/ 4.5 BA, Sleeps 16

Tejas Hills Guest Haus #2 | Hill Country + Pool

3Bed/2Bath Pool Hottub Right off Main Street

The Farmhouse: Modern Retreat in Fredericksburg

The Guest House on Elm

Stunning Fredericksburg Ranch House with POOL

Luxe Labor Day Escape | Heated Pool + Spa + Games
Destinations to explore
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- Family-friendly rentals Texas
- Family-friendly rentals United States
- Guadalupe River State Park
- Inks Lake State Park
- Pedernales Falls State Park
- Longhorn Cavern State Park
- Hamilton Pool Preserve
- Spicewood Vineyards
- Blanco State Park
- Enchanted Rock State Natural Area
- Hidden Falls Adventure Park
- Becker Vineyards
- Krause Springs
- The Retreat on the Hill
- 13 Acres Retreat
- Exotic Resort Zoo
- William Chris Vineyards
- Sweet Berry Farm
- Grape Creek Vineyards
- National Museum of the Pacific War
- Wildseed Farms
- Signor Vineyards
- Lyndon B. Johnson State Park and Historic Site
- Friedrich Wilderness Park
- Cave Without A Name
- Bending Branch Winery





