Cottage vacation rentals in Gillespie County

4.98 out of 5 average rating, 416 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, 268 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 secluded cabin is surrounded by trees, featuring a green metal roof and wooden decking. A hammock hangs nearby, and wooden railings define a spacious outdoor area. The gravel pathway leads to the entrance, enhancing the natural setting of the escape.

4.92 out of 5 average rating, 224 reviews

Lost Cabins #2 Case's Cabin

Quiet, relaxing getaway with nature AND close enough to drink some wine while shopping Main Street Fredericksburg-this is your spot. A short 16 mile drive to Main St you'll find award winning wineries, spectacular restaurants and boutique shopping! Unwind on the porch, explore, swing on the hammock gazing at the stars. Stay in to cook a meal, read a book, watch movies or gaze out the windows and see wild turkeys, cows and other country animals as time stops! 1 of 3 private cabins on the land

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, 100 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.

The exterior of the two-story home is framed by lush greenery and a manicured lawn. White rocking chairs are placed on the porch, welcoming guests. A stone pathway leads to the front door, which features a decorative sign reading 'LOVE.'

4.93 out of 5 average rating, 284 reviews

Haus Lagniappe - walking distance to Main St.

Welcome to Haus Lagniappe. Pronounced Lan-yap! Dog welcomed $100 pet fee. 2 story home The cottage is minutes walk to downtown Fredericksburg restaurant, shops, bars, distilleries, and tastings rooms. Also, we are a 10 to 15 minutes drive from multiple vineyards & tastings rooms. Lagniappe is Creole French term meaning “a little extra” We hope that Haus Lagniappe will help you to have that extra passion for life: good food, great wine, and amazing people! Wine Country.Permit8056001444

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, 111 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.

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.

4.78 out of 5 average rating, 189 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, 361 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

A comfortable seating area is visible with two gray chairs facing a wooden table. A wall-mounted television is positioned above a white fireplace. Natural light enters through a nearby window, complemented by decorative plants and soft lighting from sconces.

4.81 out of 5 average rating, 108 reviews

Main Street Retreat #12 | On Main | Pool/Hot Tub

POOL & HOT TUB UNAVAILABLE UNTIL 11/24. Located just 6 blocks from downtown Main Street, Beary Cozy is a great choice for the perfect couple. The woodwork is exquisite. Everything about this Main Street Retreat is luxurious from the outdoor swimming pool and hot tub, to its trademark his and hers vanities and designer linens and indulgent toiletries. Every piece of furniture in this beautiful cottage has an unspoken elegance to it which enhances the romantic ambiance it beholds.

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, 252 reviews

Coco Casita, Private Hot Tub, Fireplace!

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

4.95 out of 5 average rating, 101 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!