Family-friendly holiday rentals in Gillespie County

5 Blocks from Main St! Hot tub/Firepit/EV Charging

1930s cottage - 5 blocks off Main St. Walking distance to popular restaurants, music, wine bars, museums and lots of shopping. 3bed/2bath. King suite with bathroom. Walk in shower and handicapped accessible toilet. Second king bedroom, 4 twin sized bunks, and full size sofa bed. Secondary bathroom with Jacuzzi tub/shower. TVs, Wi-Fi, NEMA 14-50 outlet for EVs. Outdoor area contains fire pit, covered porch, and a HOT TUB that will add the perfect ending to your relaxing stay at Sweet Pea Cottage!

Cottage 506:Walk to Main Street/Fire pit

Located just 3.5 blocks from heart of Main Street, our farmhouse cottage exceeds expectations! Cottage 506 is located in Historic District has a spacious living room, a separate cozy sitting area with daybed/trundle, 2 large king bedrooms, and 2 dining areas. Enjoy our spacious outdoors around the fire pit. Wood provided! Being a local family, we give the best hospitality, fast responses and help customizing your stay. See our NEW luxury 2/2 and 3/3 homes on my profile page. All on Main St.

Walk to Main/Backyard Oasis/Hot Tub/Fire Sculpture

Welcome to Forty Winks! This beautiful home is the perfect place for your vacation with just a short 4 block walk to Main Street. Featuring a beautiful master suite with new tile shower w/ double shower heads, full hall bath with large tile shower, world famous kitchen, double queen guest bedroom, comfy queen sleeper sofa in living room and comfortable dining room. TVs and ceiling fans. Enjoy the newly renovated outdoor area w/ paver patio, hot tub, custom lighting, cornhole and custom firepit!

Klein Peach Cottage @ Last Stand on TX Wine Trail

Welcome to your charming retreat in the country, conveniently & centrally located on the TX Wine Trail b/w Johnson City and FBG. Immerse yourself in the heart of the Hill Country, close to wineries, distilleries, breweries, & live music within a short drive in either direction. Situated just 5 miles from Trade Days and 8 miles from the iconic Luckenbach, the serene escape is on over five acres adorned with historic live oaks, a babbling creek, darting hummingbirds, and a variety of wildlife.

The Hunters Lodge 2 BEDROOM 1 BATH CLOSE TO MAIN

Relax at the gorgeous Casita (little house) just mins from DT Fredericksburg, packed with restaurants, bars and shops. Amelia’s Casitas is a unique property with 4 inviting casitas nestled in a secluded country setting. Enjoy beautiful sunsets and the stunning Hill Country sky Comfortable design & a rich amenity list will satisfy your every need. ✔ Fully Equipped Kitchen ✔ 2 Bedrooms ✔ Free Netflix ✔ Outdoor Area (Seating, Fire Pit, BBQ) ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

The Hideaway: Modern Ranch Guesthouse

Welcome to The Hideaway, a modern ranch-style guesthouse in Fredericksburg, Tx. - King-sized bed with high-end linens and abundant natural light - Open concept living area with double-sided gas fireplace and Roku TV - Private courtyard featuring a hot tub, outdoor shower, and fire pit - Fully equipped kitchenette with mini-fridge and coffee-maker - Complimentary Wifi access - This guesthouse is completely private, no amenities are shared with other property guests.

The Fluitt Ranch house/ farm animals-River

The Fluitt Ranch is a beautiful ranch with the Pedernales River on the property dating back to 1845. Guests are welcome to interact with the chickens & Nubian milk goats. We have cattle on property please watch for them. Come and enjoy a perfect family Texas ranch getaway. Sit on our wrap around porch with a cup of coffee and enjoy the deer. Make smores under the big, beautiful sky, cook out or just relax. Take a walk to the river, swim or fish. Non smoking property

Howler Haus: 5 Blks to Main, Hot Tub,Fireplace&pit

Recent (2025) updates include stylish wood paneling, new furnishings, light fixtures, art and fresh paint! Now's the time to book your vacation with family and friends at the Howler Haus! Beautiful home with high-end furnishings and wonderful amenities. Not right for your group or dates not available? Check out the other Hill Country Weekends listings: Pool Haus (3 BD) and The Sapphire Door (4 BD). City of Fredericksburg Permit #497658

Silver Lining Cottage | 2/1, Hot Tub, Pet Friendly

Silver Lining is a private 2 bedroom, 1 bathroom contemporary cottage in Fredericksburg just a few blocks from all the action on Main Street. Guests will enjoy a full kitchen complete with full size appliances and everything you need to make a meal or heat up some fabulous leftovers. After a long day of shopping, hiking, wine tours and fun you can relax in the hot tub outside on the patio under the stars.