
Holiday rentals with outdoor seating in Gillespie County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Gillespie County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Farmhouse @ Three Windmills
We encourage you to explore our variety of activities: horse back riding, hunting, fishing, UTV rentals & more! Tres Molinos has free-roaming wildlife, goats, chickens, cows & exotics. You’re welcome to grab farm fresh eggs from the chicken coop for breakfast! Our animals are free roaming, as well as working dogs that watch over the ranch, so we require that your furry family member/s be leashed at all times when outdoors. TM is horse friendly w/stalls & arena, contact us for more information.

Around the Bend Bungalow
Craving a getaway with family or friends for wine tasting, great food and gift shopping? Want to enjoy their company, but unwind in your own space? Around the Bend Bungalow and Airstream Alfresco are located approx 12 minutes from Main St. with its abundant eateries and unique shops or 10 minutes from breathtaking views on Enchanted Rock. End your evening in a rocking chair admiring the endless stars. Longhorns wander our pastures and you share the location with an abundance of wildlife!

1/1 a Block off Main~Outdoor Shower~Tesla Charger!
The Rustic Door is a new romantic getaway just a block off of Main Street but quietly located on a running creek. The private courtyard with an outdoor shower and lounger are the perfect place to unwind with your loved one! This modern updated cabin offers peaceful outdoor seating on the front and back porches. Inside you will find a Jacuzzi bathtub for 2 and a king size bed with luxury linens. There is a kitchenette that includes a coffee bar with a Nespresso. We can't wait to host you!

Fox Burrow w/Deck acreage horses/ query for pets.
Seven minutes to Main Street, yet set on wide open green space. The cozy cabin on a private, UNPAVED road. The half acre lot has a secluded DECK facing an un-developed 10 acre pasture with cows, deer, and a 2 retired, friendly HORSES. (Sally and Adobe). Lots of beautiful space, sheep noises, and bird song. FIRE PIT for romantic nights. great STARGAZING. See pictures for amenities, NO REAL COOKING kitchenette only-microwave Pets with query only—pet cleaning fee applies Wineries near

Cottage near Fredericksburg
Relax at my unique tranquil rock cottage less than 2 miles to Main Street on the edge of town surrounded by oak trees and adjacent to peach and pecan orchards. Enjoy the sunrise on the front porch or the sunset on the back porch while relaxing to the sights and sounds of nature. Take a step back in time and enjoy relics of the past in my cottage. Sunrise Grove Cottage is best suited for a couple seeking a quiet place to stay while visiting our lovely hamlet. Man spricht deutsch.

1800’sLogCabin-PrivateRanch-KingBed-CopperBathtub
Rest easy at this luxurious and unique historic 1850’s log cabin. Minutes from Willow City Loop & Enchanted Rock. This comfy cabin is quiet, and peaceful. Historical Fredericksburg is a scenic 20 minute drive and after a day of wine tours, shopping or hiking, the cabins’ 66” Copper Tub will be waiting for a relaxing bath. Nature awaits behind the private security gates for taking a leisurely walk on the half mile “driveway” or venture out on country roads and enjoy the wildlife.

ROAM -Rooftop Hot tub/Close to Main&290 Wine/Views
ROAM is a beautiful home constructed of two repurposed shipping containers complete with nearly 1000 sq ft of deck area, great views, micro cows, and rooftop hot tub! This is the perfect place for your vacation, located right on the 290 wine trail and just outside of Fredericksburg city limits - a short drive to downtown . Spend a unforgettable holiday in the enchanting surroundings of the town of Fredericksburg, the perfect place if you like small town charm and hospitality.

Boho Vibes in the Hill Country
Here’s the RUNDOWN: - QUICK DRIVE to MAIN ST - 2 parking spots RIGHT OUTSIDE - Sleepy-time = Chill time - Bedroom w/ KING Serta i-Series mattress & 55"TV - Spacious living w/ 4K 70"TV, ATARI Console & KING pullout - Sign in to YOUR STREAMING services! - Grassy Indoor Nook w/ hammock (chill out!) - 2 private patio spaces (yes two!) w/ gas FIRE PIT - Dartboard & games - COTTON bedding - NEW SINGLE-LEVEL condo - EQUIPPED kitchen - Dining + bistro table, dual as office & island!

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.

Riddle Haus| Block off Main| Sauna| XL Hot Tub
Welcome to The historic, German homestead of your dreams, a block off of main street! Enjoy the most unique experience of Fredericksburg! This newly restored homestead comes with the ultimate surprise- a HIDDEN wine cellar! To find out how to access the cellar, you’ll embark on a short riddle experience through the home, leading you to the secret access point! Inside you’ll find the perfectly preserved wine cellar with a Hill Country prize waiting for you inside!

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 ☀️

Tempranillo Haus- Hot Tub Getaway Near Main St!
Whether you seek a romantic getaway or a rejuvenating escape to wine country, Tempranillo Haus is equipped with everything you need for an unforgettable experience. The fusion of boho modern aesthetics, romantic ambiance, and the allure of a private hot tub converge to create an oasis of relaxation. Located in the hear of Fredericksburg and only minutes to downtown where shopping, wine tasting, and delicious restaurants awaits you.
Popular amenities for Gillespie County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Charlotte's Cottage on Main St, Fire Pit!

Sonnenland - 5 Min to Downtown, Peaceful Location

Jade Haus - Beautiful 3 bedroom home

Motel Marimon: Relaxing Retreat with Hot Tub

Beautiful Home, Pool, Hot Tub & Pet Friendly

MidCentury Charm|Hot Tub|Firepit|Pets|Walk to Main

Farmhouse Hot Tub & Fireplace Min to Town/Wineries

King Beds in Quiet Neighborhood .5 Mi. to Main St
Apartment rentals with outdoor seating

Suite 2 Apartment at Brickner Guest House

Suite 4 Apartment at Brickner Guest House

Cabin Little Moon

Suite 1 Apartment at Brickner Guest House

Petit Paradis, Studio with Hot tub and In Town!

Shopkeeper's Inn Luxury Apartment.

Casa StarLight Continental Suite

Hacienda Luxury-4
Condo rentals with outdoor seating

*New Private Condo | Near Main

2BR Near Fredericksburg's Best Wineries

The Bank-Luxury Suite w/Deck Overlooking Main St!

*New Beautiful & Modern Condo| Close To Town

*NEW! Private Retreat w/Hot Tub! Sleeps 2

Beautiful Condo | Near Town | Sleeps 4

Urban Hill Country Haven

Hill Country Getaway—Serene Stay Near Fredericksbu
Destinations to explore
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- Guadalupe River State Park
- Longhorn Cavern State Park
- Hidden Falls Adventure Park
- Inks Lake State Park
- Hamilton Pool Preserve
- Pedernales Falls State Park
- Tapatio Springs Hill Country Golf Course
- Texas Wine Collective
- Blanco State Park
- Escondido Golf & Lake Club
- National Museum of the Pacific War
- Fall Creek Vineyards, Tow
- Signor Vineyards
- William Chris Vineyards
- Inwood Estates Vineyards Winery & Bistro
- Becker Vineyards
- Hilmy Cellars - Vineyards, Winery & Tasting Room
- Ron Yates Wines
- Kuhlman Cellars
- Spicewood Vineyards
- Slate Mill Wine Collective
- Bending Branch Winery
- Grape Creek Vineyards
- Boot Ranch Golf Club