Holiday rentals with a pool in Gillespie County

Upscale|Swimspa-pool|sauna|hot tub|2 blk to Main

Harmony is a gorgeous upscale home located two blocks from Main Street. The home has been custom designed to host families, couples, and friend getaways. Enjoy the open layout, spacious bedrooms and fantastic dining and kitchen areas this gorgeous has to offer. Step outside to your private backyard relaxation oasis featuring a swimspa pool, sauna, hot tub, spacious deck, sipping wine around the fire pit, or enjoying a hot cup of coffee on the front porch! Book your Hill Country getaway today!

Pink Glam House

Full Pink House? A Bachelorette party and girls weekend dream! 1 mile to Main! Master bedroom has 2 full beds with a glam suite that has 5 vanity spaces, Large Master Bath with huge walk in shower! 2nd bedroom has 2 twin beds with trundles! 3rd Bedroom has two full beds. And then there is a second bath with shower & tub + another vanity space! Large living room and kitchen with large dining table. Girls night games, fire pit, corn hole boards and a cowboy hot tub, what more could you need?!

Tejas Hills Guest Haus #2 | Hill Country + Pool

POOL RETREAT | NEAR MAIN STREET | HILL COUNTRY ESCAPE Relax at Tejas Hills Guest Haus #2 — a charming 2BR/1BA Hill Country retreat in Fredericksburg, TX featuring a private pool and spacious backyard. Conveniently located just minutes from historic 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.

Hot tub, Cowboy Pool, Pet Friendly, Fire pit!

The Container Haus is contemporary and industrial design with many unique features, recessed lighting, modern designs and countertops throughout, high quality leather furniture and lots of windows and light complete this cozy and inviting abode. You can expect to experience a great deal of fun with our outdoor patio that includes a hot tub and cowboy pool. Enjoy being in the country with country views, but also enjoy being close to downtown just minutes away. Managed by Heavenly Hosts

Airstream Glamping Near Town!

Are you looking for a fun, unique and instaworthy place to stay while in Fredericksburg? If so this is the place for you. Newley Renovated Vintage Airstream parked on our 7 acre compound just a quick 7 minuet drive to the Heart of Main Street. The interior has been completely redone with style and comfort. The perfect retreat for couples or friends who are looking for a non-traditional stay. Unwind after a long day of shopping and sight seeing in the cowboy pool while star gazing.

3Bed/2Bath Pool Hottub Right off Main Street

This exquisite townhouse is right off Main St, within WALKING distance to the heart of Fredericksburg including shops, restaurants and wineries! Enjoy your own PRIVATE courtyard with a PRIVATE splash pool, gas grill, outdoor TV, and hot tub!! Come relax in the luxurious interiors with a fireplace and stylish decor. We are pet friendly! A small pet fee of $50 per pet. This newly built Fredericksburg Farm Modern Sunday Haus has keyless entry for easy contactless check in.

Oak Casita in The Glades

Welcome to Oak Haus in The Glades on winery corridor. Take it easy at this unique and tranquil getaway. Enjoy wine at 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 two distilleries that are within one and a half miles of Oak Haus. Fredericksburg is just 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

The Silo: Modern design, private, *heated pool*

Less than 3 miles from Main Street, The Silo rests on 40 acres in the wide open space of the Hill Country providing a unique get-away. Enjoy a breath-taking sunset as you stroll down the private granite road frequented by native wildlife and blackbucks, before heading to downtown Fredericskburg for fine dining, local wines, and one-of-a-kind shopping. We want your stay to be wonderful and are happy to share local recommendations for an authentic experience.

Mesquite Treehouse @ A-Frame Ranch

Escape to a modern A-frame treehouse just outside Fredericksburg. Nestled on 17 acres, The Mesquite 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, rainfall shower, luxe linens, and modern amenities. The perfect blend of nature and comfort awaits.

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.

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!