Holiday rentals in Winters

Cute Container Cabin on Ranch w/ 50 Rescue Donkeys

Featured in Fort Worth Magazine’s “Great Texas Road Trip” (March 2024) — Chaos Ranch is a 300-acre West Texas sanctuary where rescue donkeys, wild landscapes, and modern ranch life come together. Our private 20' container cabin is ideal for solo travelers or couples who love the outdoors, want to recharge, or need a peaceful stopover to the Big Bend area. Sip coffee on the rooftop deck, hike trails, watch the stars, and learn about both the animals and the land — all in one unforgettable stay.

The Canary House -a Renovated Historic Hidden Gem!

Kick back and relax in this calm, just-remodeled space under the oak trees in historic Buffalo Gap. The master bedroom was a 1-room schoolhouse from the 1890's to 1914, where "Miss Sallie" Young taught (after she retired from 54 years in Texas public schools). After many additions and updates, it's now a quiet part of a Church Camp property (which you're welcome to explore). Perini Ranch Restaurant is nearby, as well as several other great places to eat - not to mention Abilene is 8 miles away.

Secluded railcar and caboose with incredible view

Quiet and peaceful setting overlooking Elm Valley just 9 min from Buffalo Gap. The fully renovated railcar and caboose are connected by a large back patio that boasts one of the most spectacular views in Taylor County. The railcar is the larger of the two and has a king size bed, walk in shower, full kitchen, and living area. The caboose has a queen size bed, small living area, half bath, mini fridge and coffee bar. Smart TVs and WI-FI in each. Relax and unwind at this one of a kind retreat.

Historic Reddell Guesthouse in Buffalo Gap, Texas

Guests are sure to enjoy a memorable visit in this historic, 4 bedroom/2 bath guesthouse. It is just a few miles south of Abilene in beautiful tree-filled Buffalo Gap, near the Abilene State Park and Lake and the renowned Perini Ranch Steakhouse. Guests can enjoy an afternoon of deer-watching among the oak trees, exploring the park, shopping or joining cultural activities in Abilene. Plus, it's right across the street from the famous Buffalo Gap Historic Village, which is a must-see!

Tiny House Loft on Sayles

One of a kind loft! This unique apartment was built in 1920 with our Sears Craftsman home. It has been totally renovated and updated and just might be the cutest "steampunk themed tiny house with a sleeping loft" anywhere, much less Abilene. Just minutes from downtown, the SoDA District, The Mill, bars and nightlife, all three universities and Dyess AFB. Our Historic Sayles Loft is perfectly located for one night, a weekend, or more! It’s a tiny space, so two guests is the limit!

1886 De-Constructed: 1 King, 2 Fulls, 1 Bath

1886 De-constructed: This unique 2-1 apartment is spread across the entire 2nd floor of a historic downtown Ballinger building. Recently remodeled from 1950's era offices into a beautiful living space boasting 14' ceilings, gorgeous original windows, and over 3k sqft of living space. The stone and shiplap walls have been uncovered and are on full display after being hidden for over 130 yrs. A variety of locally owned boutiques, antique stores, and restaurants are just steps away.

Modern, cozy duplex close to downtown!!

Very simple, but beautiful and comfortable place to stay. You will be staying in one apartment of a duplex. Only 7 minutes away from downtown Abilene (by car), where you can find amazing cafes (Front Porch Cafe, Monk's cafe), and restaurants (Vagabond Pizza, The Local). House is located to close to Sayles Boulevard and Butternut street, which makes it a breeze to get around. There is also an air mattress that you can use for the 5th and 6th person. Thank you!!

Rustic Cabin in the Hills

Rustic, cozy two room, eclectically decorated cabin. A peaceful, safe retreat or way station with views of the surrounding Callahan hills. Enjoy the milky way at night and In the spring and summer enjoy our beautiful wildflowers. Lake Abilene State Park is a 5 minute drive down the road. Non-Smoking. Lola the house corgi lives on the property. Please NO PETS, of any kind. We follow AirBnb guidelines for cleaning and disinfecting.

Hollywood House is all about charm and comfort!

Relax with the whole family in this peaceful place to stay with all of the comforts of home! 3 Bedroom, one story home with large back yard that has alley access for extra parking if needed for boats. Propane gas grill and outdoor seating. Fully stocked kitchen with gas range and dishwasher. Washer and Dryer. Fairly close to OH Ivie lake where a Texas angler reeled in an 'historic' bass, one of the largest of all time in February 2023!

Cottage on Commerce

Just a few blocks from downtown Winters, TX shopping and restaurants, this little cottage is nestled in a quiet neighborhood with a front yard and large trees. Drinks and snacks are complementary to all of our guests. Whether you are passing through or here to enjoy a quiet weekend, you will be treated as our special guests with amenities such as Wi-Fi, waters, snacks and an assortment of movies, games and books.

Country Experience at Dug Out Hideaway

The Dug Out Hideaway is on 10 acres in the country, on the side of a mesa. We have hiking trails through a cedar forest. Wildlife such as deer, fox, racoons, and coyotes could be seen at the feeder near the house. Clear beautiful night sky. Spectacular view overlooking Abilene and countryside. Waterfall on back patio with a view of the mountainside. Large fort for kids to play in.

“Serendipity” a Boho inspired tiny home / Hot Tub

You’ll treasure your time at this memorable place. “Serendipity” is a Bohemian style tiny home on wheels nestled among the West Texas Mesquites. You have your privacy and yet less than 10 minutes from town. There is a full bathroom with shower, a queen size bed in the loft and a daybed on the main floor. Relax under the stars in your private hot tub.