Vacation rentals with a pool in Gillespie County

The Downtown Studio 3, Hot tub, Cowboy Pool!

Need to get away for a few days and enjoy some time in our quaint little town? Wine tasting maybe? Book this recently remodeled studio, just 2 blocks from the heart of it all and wake up, enjoy a cup of coffee from the Keurig coffee maker and go exploring! Afterwards come back and relax in your own private hot tub. Did we mention the location? This studio is in our beloved historic district just steps to all the festivals and festivities Fredericksburg is known for. Managed by Heavenly Hosts

The 1851 Cabin at Wolf Creek Guest Ranch

The Wolf Creek Guest Ranch is the perfect place to experience an original log cabin on a private working horse ranch. The cabin was originally built in Arkansas in 1851, carefully taken down and rebuilt into a very comfortable rental. Guests will find this beautiful cabin equipped with air conditioning, heat, a soaking tub, and a huge stone fireplace to enjoy on those winter nights after a day of wine tours, shopping, restaurants and outdoor activities that Fredericksburg has to offer.

Winter Cheers with Wine, Heated Pool, Firepit!

This 3 bedroom (6 beds)-2 bath home is the perfect spot for your family gatherings, friends trips, or the romantic getaway! Are you looking to unwind? You have options! Check out the growing cuisine of Fredericksburg, award-winning Texas wines, or choose to relax in our newly installed swim spa . What is a swim spa? Your choice whether you want a cooling swimming pool or a heated, jetted pool. This is the place for your next vacation! *No longer a hot tub but still heated swim spa!

Luxury Tree House X Magical Romantic Forest! Pool!

Imagine being immersed in a small enchanted forest only 100’s of feet off of Main street. Nestled into live oak trees that gently sway in the breeze, under dark skies with bright stars, and curated to both inspire joy and create presence. Welcome to our little magical treehouse and landscape resort in Fredericksburg. The amazing stays in our secluded forest are only minutes to all of the beautiful shops, cafes, restaurants, bars, and Vineyards. A magical stay that we hope you will love.

Near Main ~ Swimming Pool & Stunning Outdoor Area

The Travis House is a gorgeous 1960's ranch style home that has been totally transformed and updated into a beautiful bright and airy home! With a BRAND NEW PRIVATE SWIMMING POOL AND HOT TUB and located just 3 blocks from Main Street on the west end of town, you will not find a more perfect location for your large group! The Travis House is made up of 4 bedrooms, 2 baths and 2 living areas, & a makeup area to get ready! Only one mile to Hondo's Crossroads & Altdorfs. Permit #8056001175

Pecan Casita in The Glades

Welcome to Pecan Casita in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine around the fire pit or coffee on the porch, where deer might scamper by. Spend your time relaxing, playing games or swimming in the heated cowboy pool (which is a 10 foot stock tank) in the common leisure corral. Visit the 12 wineries, brewery or 2 distilleries that are within one and a half miles of Pecan Casita. Fredericksburg is a short drive away.

The Farmhouse: Modern Retreat in Fredericksburg

Welcome to The Farmhouse, a modernized 1930’s craftsman home on a family-owned homestead in Fredericksburg, Tx. - Private guesthouse with expansive outdoor entertainment area - Master bedroom with king bed, private bathroom, and Roku TV - Additional bedrooms with king beds and shared bathroom - Full kitchen and dining for 10 - Freeform swimming pool with grotto waterfall - Outdoor kitchen with gas grill and dining space - Complimentary Wifi access

Tejas Hills Guest Haus #2 | Hill Country + Pool

POOL RETREAT | NEAR MAIN STREET | HILL COUNTRY ESCAPE Relax at Tejas Hills Guest Haus #2 — a cozy 2BR/1BA Hill Country retreat with a private pool and spacious backyard. Conveniently located near Fredericksburg’s Main Street, local shops, and restaurants. Minutes from Wine Road 290 wineries, breweries, and Enchanted Rock. The perfect spot to unwind, sip local wine, and soak up the Hill Country sunshine with family, friends, or that special someone.

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 ☀️

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.

3B/2B Pool & Hot Tub- 1 BLK to Main!

Cozy comfortable cottage one block from Main Street! Walking distance to popular restaurants, bars, shops and museums. Very convenient to wineries- perfect place for friend and family gatherings. Large backyard includes covered living space with fireplace and grill, private pool with hot tub, fire pit sitting area, and plenty of space for lawn games. You will feel right at home at the Henning Haus!

Chic Retreat, Pool, Hot Tub and Pet Friendly

Bachelorette Party? Wine Tasting? Family Vacation? Welcome to Acorn Haus, your stylish Fredericksburg retreat! Perfect for any occasion, this 3-bedroom gem is just minutes from historic Main Street and the heart of Texas wine country. With its unique modern farmhouse and boho-chic decor, every corner is designed for creating unforgettable moments. Dive into the heart of Fredericksburg with us! 💫