Holiday rentals in Winters

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Top-rated holiday rentals in Winters

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Top guest favourite
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
4.97 out of 5 average rating, 203 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 favourite
A charming treehouse is nestled among large oak trees. A spiral staircase leads to a balcony with a view. The surrounding area features a grassy lawn and a wooden swing hanging from a nearby tree, creating a serene outdoor setting.
Treehouse in Baird
4.98 out of 5 average rating, 227 reviews

Ryders Treehouse: Romance, Privacy, and Fishing!

A peaceful, private treehouse retreat on an 800-acre ranch—perfect for romance, relaxation, and outdoor adventure. Enjoy stunning sunrises, sunsets, and stargazing in total seclusion. Spot wildlife, hear wolves howl, and wake up to cows and horses grazing nearby. Go fishing in stocked ponds, unwind by the fire, and experience the magic of nature. Enjoy a cozy outdoor shower / complimentary wine. Need more space? View our Magical Treehouse w/ a hot tub: www.airbnb.com/rooms/1050765478693854760.

Guest favourite
A panoramic view of rolling hills is displayed, featuring lush green vegetation under a clear blue sky. The horizon showcases distant hills, enhancing the serene, natural setting of the property.
Guest house in Tuscola
5 out of 5 average rating, 23 reviews

Hilltop Hideaway, The Honey Haus

Come escape to the peaceful outdoors in the Honey Haus for two. Sit outside on the patio with your favorite drink and capture the breathtaking views. There is an infinity swimming pool waiting for you showcasing beautiful sunsets. A propane grill and mesquite smoker for your dining pleasure are provided. Enjoy smores around the firepit or sit back and enjoy the stars! Excellent retreat no matter whether hunting, attending an event close by, or just wanting to relax for a romantic getaway!

Guest favourite
A cozy sleeping area features a queen bed dressed in light bedding with decorative pillows. Two nightstands with lamps are positioned on either side. Dark curtains hang elegantly over a window, while woven wall art adds visual interest to the room.
Guest house in SunnHaus Brewing
4.85 out of 5 average rating, 150 reviews

Petite Retreat (Pet Friendly - 1 Small Pet Only)

This cozy cabin escape is perfect for solo travelers or couples seeking a secluded, safe, and affordable place to unwind. Designed for comfort, the space includes a queen bed, a private bathroom, and a functional wet bar equipped with a mini fridge, microwave, and Keurig coffee maker. While it doesn’t offer a living room or kitchen, the retreat provides everything you need for a comfortable stay including fiber optic internet and WiFi. Pets are allowed but limited to one (1) under 35 lbs.

Top guest favourite
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, 133 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 favourite
A spacious living room features a comfortable sectional couch adorned with decorative pillows. A round coffee table sits centrally, with a Smart TV mounted on a white console against the wooden wall. Natural light enters through windows, enhancing the warm wood tones throughout.
Cabin in Coke County
5 out of 5 average rating, 123 reviews

The Cabin

Our cabin is in north Coke County near the small ghost town of Sanco. The property has been in our family for 5 generations. It offers beautiful views, sunrises, sunsets and star gazing. Come enjoy the views from the wrap around porch or the comforts of the couch. The small town of Robert Lee is just 5 minutes south where you will find Lake Spence, a 9 hole golf course, coffee shop, boutique and 2 restaurants. We are centrally located near, San Angelo, Abilene and not far from Midland.

Top guest favourite
A welcoming front porch is showcased with wooden flooring and comfortable seating options. A bright red door stands as the focal point, with decorative signs nearby. Flowering plants are arranged in the mulch bed, adding touches of natural beauty to the inviting entryway.
Guest house in Buffalo Gap
4.95 out of 5 average rating, 127 reviews

Country cabin close to the city

The cabin is located on a gated and fenced six acre property just outside of Buffalo Gap offering great security to our guests. It’s a quiet country place but only 10 miles from the Mall of Abilene. It’s very close to the Abilene state park, the historic village, Beltway Park Church, Wylie and Jim Ned Schools, and the world famous Perini Steakhouse. It is about 20 minutes from ACU or HSU. The property and surrounding area is great for walks and there is a Dollar General close by.

Guest favourite
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.
Flat in Ballinger
4.98 out of 5 average rating, 126 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 favourite
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, 194 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.

Superhost
Home in Winters
5 out of 5 average rating, 4 reviews

1950s Ranch Style House

Enjoy a stylish experience at this centrally-located, newly remodeled 1950s place. 3BR/2 Bath. New appliances. Full kitchen. New Central AC & Heat. Furnishings, cookware, linens, towels, washer dryer, TV & Internet. Ideal for professionals working in or near Winters Tx or for someone visiting family for an extended period of time. 5 day minimum to a few months. See my other listings.

Top guest favourite
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, 170 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.

Guest favourite
Home in Buffalo Gap
4.94 out of 5 average rating, 229 reviews

Southern Comfort: Cozy Retreat in Buffalo Gap, TX!

Discover a charming cottage-style home in the rolling hills of Buffalo Gap, Texas. This artistic retreat features original artwork, eclectic furnishings, and a warm, cozy atmosphere. Enjoy two comfortable bedrooms, each with a private en-suite bathroom—perfect for couples, friends, or small groups.

Popular amenities for Winters holiday rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Runnels County
  5. Winters