Family-friendly holiday rentals in Gillespie County

Close to Main- Pool, Hot Tub, Family Friendly

Located just off Main Street, Bell Street Bungalow is the perfect destination for a girls getaway, couple's retreat, or family weekend in Texas Wine Country. The home has 2 bedrooms, a bathroom, and game room in the main house in addition to a 1 bed/1 bath cottage in the backyard; both included in your stay. Enjoy the hill country outdoors by the private in-ground pool, hot tub, fire pit, and grill area. The home is a mile from the best downtown destinations and a short drive to many wineries.

Kitchen · Family · Decor

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.

Kitchen · Family · Location

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!

Family · Indoor spaces · Pool

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.

Family · Indoor spaces · Heating

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!

Kitchen · Indoor spaces · Air conditioning

Vineyard-City on a Hill at Spring Creek

City on a Hill at Spring Creek  in Fredericksburg,has four deluxe, private cabins overlooking Spring Creek! Although the cabins are only 10 miles from town, guests feel as if they are in another world; a world of pure Texas Hill Country! A king size bed with elegant hill country style bedding and large bathroom. The bedroom/sitting area includes a flat screen TV; kitchenette complete with a toaster oven, full size refrigerator, keurig and microwave. Large porch with hot tub.

Indoor spaces · Kitchen · Heating

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.

Kitchen · Indoor spaces · Sleep quality

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

Kitchen · Family · Air conditioning

Stunning Villa w/ Sheep, Donkeys, Hot Tub, Wine

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, 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.

Family · Kitchen · Pets

Moonrise Retreat, a taste of country peace...

Pet-Friendly Country Cabin on 15 Acres – 4 Miles from Main Street! Enjoy peace and quiet just minutes from downtown Fredericksburg. This cozy cabin sits on a scenic 15-acre farm with hill country views and friendly animals—including a mini horse, donkey, cows, and more. The cabin is private, quiet, and comfortable—just 50 yards from our home, but we give you space to relax. Pets welcome, and there’s even an EV charger for your convenience.

Kitchen · Family · TV

Rockin' R - Morning Star Cabin

Escape your cabin fever with a rejuvenating retreat at our 'Morning Star' cabin, one of the six custom-built havens at Rockin' R Ranch Cabins. Nestled on 10 acres of pristine land, this cozy cabin offers a tranquil escape surrounded by abundant wildlife. Step away from the rapid pace of city life and immerse yourself in the serenity of the Morning Star. Plus, indulge in the captivating hill country view right from your front porch!

Family · Indoor spaces · Comfort

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.

Family · Indoor spaces · Layout