Vacation rentals in Winters

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Top-rated vacation rentals in Winters

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Top guest favorite

A converted shipping container accommodation features a rooftop deck with seating and a staircase for access. The exterior is black, and a picnic table and additional seating are placed nearby. A vibrant sunset paints the sky in warm hues, enhancing the peaceful rural landscape.

Farm stay in Miles

5 out of 5 average rating, 131 reviews

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.

Top guest favorite

A rustic wooden cabin is seen with a vibrant red door, surrounded by lush green trees. Benches are positioned on the deck, and Adirondack chairs are placed in the yard, creating a welcoming outdoor space for relaxation.

Home in Buffalo Gap

4.99 out of 5 average rating, 135 reviews

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.

Top guest favorite

The roof of the caboose provides a vantage point overlooking the lush greenery of Elm Valley, with expansive skies painted in soft hues of orange and blue as the sun sets. The serene landscape evokes a sense of tranquility and open space.

Train in Tuscola

5 out of 5 average rating, 104 reviews

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.

Top guest favorite

A two-story guesthouse is displayed under a blue sky with scattered clouds. The front features a centrally located entrance surrounded by two balconies, each adorned with wooden railings. Large windows provide natural light, and the grassy lawn extends towards the home.

Guesthouse in Buffalo Gap

4.97 out of 5 average rating, 113 reviews

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!

Guest favorite

The historic building features a light-colored façade with arched entryways. Street signs indicate Hutchings Avenue, while traffic lights hang prominently above. Large windows illuminate the front, and iron fencing lines the sidewalk, contributing to the building's classic architectural charm.

Apartment in Ballinger

4.99 out of 5 average rating, 112 reviews

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.

Top guest favorite

The exterior of the home showcases a modern design with a combination of grey and turquoise hues. Floor-to-ceiling windows create a bright façade. Beneath an overhang, four bright chairs are positioned, inviting relaxation. A landscaped garden with stones and plants frames the front yard.

Loft in Coleman

4.95 out of 5 average rating, 179 reviews

The Loft at Stardust Retreat

Spacious hilltop mid-century modern loft renovated with modern conveniences and filled with vintage furnishings & art. The airy space commands stunning views from its second level floor-to-ceiling windows, while enjoying peace on the private, wooded 3-acre property. The perfect country getaway, in style! * Spacious living room * Fully equipped kitchen * 2 king bedrooms * Large covered patio * Privacy w/self check-in * Amazing hilltop views * 2 min to downtown Coleman

Top guest favorite

An open-concept living area features a queen-size bed with a plaid headboard, complemented by a checkered rug. A cozy red couch and a small table are situated near the front door. Wall-mounted decor and a window adorned with checkered curtains create a rustic, welcoming ambiance.

Tiny home in Sweetwater

4.97 out of 5 average rating, 229 reviews

Unique Tiny House with Queen Bed and Hot Tub

A cozy 280 sq. ft. tiny house in the country is a great place to take it easy, unplug and enjoy the West Texas sunsets, star gazing and wildlife. Less than 10 min. from some of the best BBQ in West Texas, World's Largest Rattlesnake Roundup (March) and minutes from area lakes for great fishing. The home has an open concept kitchen, living room and queen size bed. The bathroom features a large metal stock tank bathtub with shower. Secure parking area.

Guest favorite

A well-groomed corgi sits among vibrant wildflowers, capturing the cabin's charming outdoor space. The rustic cabin and bicycles are visible in the background, highlighting the inviting ambiance of the property.

Guesthouse in Tuscola

4.93 out of 5 average rating, 320 reviews

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.

Guest favorite

A single-story home is presented, featuring a white exterior and a covered porch. Large windows allow for natural light, while a green lawn surrounds the property. A walkway leads to the front door, providing access to the welcoming entrance.

Home in Coleman

4.94 out of 5 average rating, 151 reviews

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!

Guest favorite

A king-sized bed is positioned against a pale wall, adorned with a variety of decorative pillows and a patterned blanket. A bedside table holds a lamp, while a framed quote hangs above, adding a personal touch to the cozy sleeping space.

Cottage in Winters

4.97 out of 5 average rating, 193 reviews

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.

Top guest favorite

A spacious house sits against a backdrop of lush greenery and a hillside, surrounded by open grassy areas. The structure features a large deck that extends from the front, with parking available under a carport nearby. Natural rock formations are positioned prominently in the foreground.

Home in Tuscola

4.96 out of 5 average rating, 139 reviews

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.

Top guest favorite

A single-story brick house features a well-maintained front yard with lush green grass. An American flag is displayed outside, and a paved driveway leads to the entrance. Large windows allow natural light to fill the home.

Home in Abilene

4.99 out of 5 average rating, 103 reviews

Relaxing 3-bedroom home with a beautiful backyard.

Whether you stay for 3 nights or an entire month, you will enjoy this relaxing and peaceful home away from home. There is plenty of closet space, a laundry room, and a beautiful backyard with two water features. The view from the back yard is limitless and you won't find a more beautiful sunrise or sunset.