Cottage holiday rentals in Gillespie County

4.98 out of 5 average rating, 430 reviews

Wine Country Sanctuary | Your Private Eco Retreat

- QUICK DRIVE to Main - LARGE PRIVATE PATIO w/ FIREPIT & GAMES - 2 FREE parking spots RIGHT OUTSIDE - 55” 4K SMART TV & KING MATTRESS: Sealy High Point Hybrid - 70" 4K SMART TV, PATIO & PORCH VIEW in COZY living for 4, w/ QUEEN pullout - Sign in to YOUR STREAMING services - ATARI console games - COTTON bedding & towels - EQUIPPED kitchen - bistro DINING & DESK - a SPACIOUS BATH w/ NEW stand-up shower - FREE LAUNDRY access - SINGLE-LEVEL cottage-style condo - MINIMAL aesthetic - ECO choices w/ ♡

A private tiled deck features a bistro table and two chairs, surrounded by colorful patterned tiles. A vase with fresh flowers adds a touch of vibrancy. The serene Hill Country landscape is visible beyond the railing, providing a peaceful backdrop.

5 out of 5 average rating, 275 reviews

Cozy, chic APT near Main St w country view

Colorful, modern apt with full kitchen & a guest-only private deck w scenic view. Super location. Quiet street. Doors between rooms. 440 mbps internet. 2:00pm ck in. You're the only guests we host. Contactless chk in/out. PLUS rsrv'd off-street parking. 7 safe blocks to Main St & downtown. Wide country landscape view: sheep & cattle grazing from the secluded tile patio. Enjoy coffee, sip wine, star gaze. Serene. Beautiful view Romantic & private. We welcome guests from all backgrounds

A gravel pathway winds through a serene landscape flanked by green trees and shrubs. A white wooden fence borders one side of the path, while a rustic wooden fence outlines the opposite side, offering a tranquil entrance to the ranch.

4.93 out of 5 average rating, 104 reviews

Cozy Cottage | Near Wineries | Sleeps 6 | Hot Tub

Located within 4 miles of the 290 wine trail, this two bedroom country cottage is great for an escape from city life. The house is located on a 300+ acre working ranch, with access to the Pedernales River. The bedrooms have a queen size bed with luxury linens and a bathroom with a champagne bubble tub and walk-in shower. The hot tub on the private porch is great to relax in after a long day of Main Street shopping or wine tasting. Come see why we call Monarc Ranch our little piece of heaven.

A modern cottage exterior is featured, showcasing a light metal roof, wooden beams, and an inviting porch area. Gravel paths lead to landscaped spaces with native plants. Large windows provide a view into the home, reflecting a connection with the surrounding nature.

4.99 out of 5 average rating, 113 reviews

Beautiful and private hill country cottage

Starry night skies and wildflowers abound at this hill country treasure. Located between Kerrville, Harper and Fredericksburg, the perfect location for visiting local wineries, shopping, theater and more. The 2-bedroom, 1-bath cottage is situated on 56 private acres with lots of wildlife and views. Built in 2021, the modern farmhouse-style cottage is clean, comfy and cute as a button--just right for up to 4 people. Please note that the property is not designed to accommodate young children.

A serene landscape reveals a charming stone cottage nestled among lush greenery. The cottage, framed by large trees, reflects in the still waters of a pond, creating a peaceful ambiance under the soft glow of a setting sun.

4.92 out of 5 average rating, 119 reviews

The Grapetown Gasthaus @ TimberRose Ranch hot tub

Perfect getaway for 2. The name of the cottage honors the local area of Grapetown. Crossing thru a cedar privacy screen takes you to this native stone cottage crafted by a local artisan and features antique doors with layers of turquoise, exposed wood. The living area has TV / DirecTV, a leather loveseat, dinette and stocked kitchen. There are beautiful views from in and out. A copper heating grate and a transom window are featured. Charcoal grill, fire pit, hot tub to go with your wine!

Superhost

The cottage features a welcoming facade with a gabled roof, a covered porch with seating, and stone pathways leading to the entrance. Surrounding vegetation and open fields create a tranquil setting against a colorful sky at dusk.

4.79 out of 5 average rating, 208 reviews

Das Grun Haus With Private Hot Tub!

Welcome to Das Grun Haus! This beautiful cottage is a cozy, rustic hideaway just a short drive from Main Street. (8 miles) This delightful two bedroom, two bathroom cottage is perfect for some "ahhhhh time." The cottage sleeps six and features a private backyard with a hot tub, fire pit, and charcoal grill. The home is equipped with high quality memory foam mattresses and luxurious linens and towels. The cottage is located on 10 acres with one other home and one tiny home on the property.

The cozy sleeping area features a spacious bed with a neutral-toned duvet and decorative pillows in soft pink hues. Warm light from bedside lamps casts a gentle glow on the textured walls, while plush curtains frame the headboard, enhancing the serene ambiance.

4.8 out of 5 average rating, 369 reviews

Amore: Cozy romantic carriage house w/ hot tub

This crown jewel of Bloomingwild, originally a true carriage house, is now a rustic romantic private guest cottage less than two blocks from Main Street. Amore Dolce features a deep tub for two set in limestone with a skylight and separate shower. Other amenities include a full kitchen, king bed, a cozy nook with twin bed, upstairs loft has a comfortable sitting area with TV. You'll find a private hot tub on your secluded back porch. Make Amore Dolce your “sweet love” heaven! Permit#13473

An inviting outdoor area features a private hot tub next to a cozy fireplace, set against a backdrop of vibrant sunset hues. The space is surrounded by trees, with warm lighting adding a tranquil ambiance to the patio's relaxing setting.

4.94 out of 5 average rating, 260 reviews

Coco Casita, Private Hot Tub, Secluded!

This adorably appointed cottage located on 6 acres of woods is ideal for couples and for stargazing! The incredible outdoor space includes an enormous fireplace, private hot tub, lovely landscaping, Weber grill, beautiful outdoor furniture & hammock! Inside you'll find a cozy ambient fireplace, designer decor, full kitchen, wonderful king canopy bed with lush linens, & shower for two! Coco Casita is the ideal couples escape! Simply romantic! Managed by Heavenly Hosts

4.96 out of 5 average rating, 115 reviews

Private Wellness retreat|Hottub|Sauna|Prime loc

★ "Absolutely fantastic get away, the vibe was romantic and the place was perfect." 🏡 3 blocks to FBG’s East Main St—stroll to wine tasting rooms 🔥 Secluded yard with sauna, hot tub, fire pit 🏡 Perfect cozy cabin vibe couples getaway with total privacy 🛏 King bedroom with super comfy bedding 🥘 Fully equipped kitchen 🏑Fun loft space with air hockey table 🐶 Dog friendly Everything is set for your romantic Hill Country escape—book now before the calendar fills!

Cottage in Gillespie County

A light-filled room features a king-size bed adorned with soft linens, complemented by a wooden headboard. The ceiling is vaulted, showcasing wooden beams, while artwork adorns the walls. A nightstand and a dresser provide functional charm, surrounded by large windows with sheer curtains.

4.89 out of 5 average rating, 456 reviews

Casita Azul PRIVATE STUDIO 5 Min Drive to Downtown

Beautiful newly built studio style Casita. Enjoy the peace & quite of the Texas Hill Country while being just a few miles away from downtown Fredericksburg. The Casita is equipped with WiFi and a Smart Tv. We also provide a coffee bar set up for your enjoyment as well as an outdoor area with a fire pit and seating. Bbq pits are on the property so bring some steaks to grill and your favorite bottle of wine to dine under the stars! We hope to see you soon

The exterior of a farmhouse is showcased, featuring a welcoming porch adorned with two light blue chairs. Rustic wagon wheels are mounted on the walls, while the sky above transitions with hues of orange and pink as the sun sets. A wooden fence encloses the property.

4.97 out of 5 average rating, 492 reviews

Cute Farmhouse - alpaca, donkey, sheep & hot tub!

The Farmhouse at Spotted Sheep Farms is a Texas chic property and is perfect for a wine country getaway. The property is home to animals and wild life including alpacas, llamas, miniature donkeys, miniature sheep and of course, spotted sheep! It boasts an open floorplan with full kitchen, queen bedroom, loft with two twin beds, brand new HotTub, satellite TV, WiFi, Netflix, outdoor games, fire pit, and large porch to watch the sunset and farm animals.

A spacious living area is furnished with comfortable seating, including chairs and couches arranged for conversation. Natural light fills the room through multiple windows, highlighting a decorative wall map and artwork. A table with books and decorative items is positioned near a unique light fixture.