Holiday rentals with a pool in Gillespie County

4.97 out of 5 average rating, 200 reviews

2 blk to Main.All season pool,sauna,hot tub

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!

A split-image showcases a cozy living area with a large television mounted on a dark feature wall and a warm seating arrangement. The outdoor space features a heated swim spa and comfortable patio seating surrounded by a well-maintained yard and landscaped stones.

4.96 out of 5 average rating, 105 reviews

Close to Main, Heated Pool, Firepit, 220EV outlet!

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!

4.97 out of 5 average rating, 345 reviews

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.

Superhost

4.88 out of 5 average rating, 146 reviews

Hot tub, Cowboy Pool, Pet Friendly, Close to Town

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

Superhost

A vintage Airstream is parked on a gravel surface, reflecting sunlight. In the foreground, a cowboy pool is visible, with a person relaxing inside. The backdrop features an open field under a clear blue sky, creating a spacious and serene outdoor environment.

Tiny home in Fredericksburg

4.75 out of 5 average rating, 104 reviews

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.

A modern building is presented with a spacious covered porch supported by sturdy columns. Dark railing surrounds the porch, where a set of chairs is visible. The structure is surrounded by natural landscaping, featuring trees and a gravel pathway leading to the entrance.

4.97 out of 5 average rating, 101 reviews

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.

4.98 out of 5 average rating, 169 reviews

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

An outdoor deck features a glimpse of a plunge pool surrounded by natural scenery. Two lounging chairs are positioned next to a small dining table. The sky displays soft pastel hues during sunset, enhancing the tranquil setting of the area.

5 out of 5 average rating, 259 reviews

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 ☀️

A charming cottage, painted in soft yellow, features dark green shutters and an inviting porch. Rocking chairs are positioned on the covered entry, surrounded by lush greenery. A white picket fence encloses the front yard, enhancing the home's welcoming exterior.

4.96 out of 5 average rating, 165 reviews

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!

4.96 out of 5 average rating, 124 reviews

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! 💫

4.91 out of 5 average rating, 445 reviews

The living area is characterized by large windows that invite natural light and offer a view of the surrounding trees. A modern sofa and an accent chair are positioned around a wooden coffee table. A wall-mounted TV is present, enhancing the space's functionality.

Cabin in Fredericksburg

Modern A-Frame Cabin in Nature, Minutes from Main

Stay in a modern A-frame cabin on 17 scenic acres just outside Fredericksburg. The Comal sleeps 2–4 with a king bedroom, open loft, and sleeper sofa option. Relax on the deck, grill dinner outdoors, lounge in the private stock tank pool (with optional heater), or gather around the propane fire pit under starry skies. Less than 10 minutes to Main Street, this is the perfect Hill Country escape.