Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite
A spa room features a large hot tub with bubbles and soft blue lighting surrounding the ceiling. A small chair sits nearby, and a television is mounted on the wall, displaying an image. Wooden paneling adds warmth to the space.
Cabin in Smithville
5 out of 5 average rating, 107 reviews

River-Shack

Your very own slice of heaven awaits you!! You will be nestled discreetly in the woods, above the Colorado River Camp. In this unit you’ll enjoy seclusion & privacy from the camp. You can fish, you can swim, you can bird watch, you can explore, or you can always just relax in the hammock and forget all your worries friend!!! You’re a click away from a one of a kind stay you will never forget! Nature enthusiasts, This Is Your Spot! PSA THE SPA IS ENCLOSED NOT INDOORS!! INSECTS MAYBE SEEN!!

Top guest favorite
A riverside picnic area features a simple wooden table surrounded by grass and stone. An active fire pit, with flames flickering, adds warmth to the scene. The tranquil Colorado River and lush trees create a serene backdrop.
Tiny home in Smithville
4.99 out of 5 average rating, 127 reviews

Colorado River Romance/Glamp/Fish/Float/Pup-heaven

Dive deep into a picturesque countryside haven alongside the tranquil Colorado River. Here, every twist and turn unveils amazing views to become your shared stories of nature's serenity. Join the River RV family of guests. Revel in peaceful nights beneath a star-studded sky, with the firepit's glow complementing the river's lullaby. Experience luxury with a king bed, a fully-equipped kitchen, and opulent theater seats. This is where enchanting sunsets meet dawn's promise of adventures anew.

Guest favorite
A charming treehouse constructed from natural materials is nestled among lush greenery. Its distinctive round windows and unique entrance door are highlighted, while a wooden bridge connects it to the surrounding landscape. The sky overhead is partly cloudy, adding to the enchanting ambiance.
Treehouse in Paige
4.94 out of 5 average rating, 132 reviews

The Hobbit's Nest

Escape to a world of magic and wonder with a visit to the enchanting Hobbit's Nest treehouse. Whether you seek a romantic getaway or a fun-filled family vacation, this unique glamping experience offers the serenity of nature with all the comforts of home. Resting amidst the lush treetops of Lost Pines Forest, the Hobbit's Nest promises an unforgettable stay where your imagination can run wild and your soul can find solace in the beauty of the natural world in the 42 acre Lost Pines Shire.

Top guest favorite
A charming cottage features a sturdy wooden door framed by large glass windows. The surrounding landscape includes well-maintained mulch beds with ornamental plants and a stone pathway leading to the entrance, while trees provide a natural backdrop.
Cottage in Smithville
5 out of 5 average rating, 145 reviews

Domovina Ranch Cottages ("The FW")

We offer two beautiful cottages (The Hemingway and The FW) that are located on 50 acres at the end of a dead end road. Surrounded by thousands of privately owned acreage, featuring abundant wildlife (deer, turkey, birdwatchers paradise). This is a working cattle ranch so you can take in sunsets as cattle graze in front of you. Cottages are newly built and fully furnished. Lofts for reading, custom tile showers, outdoor fire pits and lounge area. Cottages are located away from main house.

Top guest favorite
The rustic cabin is enclosed by tall pine trees, showcasing a wooden exterior. A small porch is accessed by steps, featuring two red rocking chairs. An American flag hangs visibly, and a satellite dish is mounted on the roof under a clear sky.
Cabin in Smithville
4.93 out of 5 average rating, 276 reviews

Best Little Cabin in Texas

Secluded cabin on 200 acres of private pine forest. Enjoy hiking & views from large deck. Cabin's decor based on local legend & Broadway hit, The Best Little Whorehouse in Texas, replete with the madam's bed. Fully stocked kitchen with coffee maker, microwave, & dishwasher. BBQ on the outdoor propane grill and enjoy a campfire under the stars (bring your own firewood). 2 miles off highway. Pets OK with a $25 per pet fee. Up to three. Please let us know if you’ll be bringing yours.

Top guest favorite
A quaint house features a blue exterior with a metal roof. A porch swing hangs adjacent to a white railing, with two windows visible. A tree stands nearby, providing shade to the porch area.
Home in Lexington
4.96 out of 5 average rating, 187 reviews

Sunset View

A cute little house in the country. Come enjoy a few peaceful days with a gorgeous view of the sunset while watching the cattle graze in the field. Also enjoy the porch swing. The house is clean and comfortable to stay in. There is a queen bed to sleep in, a nice TV to watch with directv, and there is also internet service. A great place to unwind or venture out. We are 17 miles from Lexington, 17 miles from Elgin, 23 miles from Taylor, and 45 miles from Austin. Come see us!

Top guest favorite
A modern open-concept cabin space features a spacious bed with crisp white linens. Natural light filters through large windows, revealing views of the surrounding trees. A kitchen area includes bar stools and a microwave, offering a warm, inviting setting amidst nature.
Farm stay in Cedar Creek
4.97 out of 5 average rating, 177 reviews

Relaxing Ranch, Friendly Animals, Modern Stay

Unwind in this modern cabin where nature meets comfort. Enjoy an interactive experience with friendly farm animals eager for pets and treats. Soak in views of the serene pond, grazing cows, and horses. Explore trails on secluded acreage. Light-filtering blinds, AC, and Starlink WiFi. Built in 2023. We have piggies, mini goats, cows, horses, donkeys, and a black lab to say hello to Close to Circuit of the Americas, Bastrop, Austin Airport, and Smithville.

Top guest favorite
A modern two-story structure, surrounded by tall pine trees, features large windows allowing natural light to fill the interior. A spacious deck offers two lounge chairs, inviting relaxation. The swimming pool is partially visible, enhancing the outdoor experience in the serene forest setting.
Cottage in Bastrop
4.98 out of 5 average rating, 225 reviews

Paradise Pines

Private. Peaceful. Hugged by the forest. A romantic getaway or refuge from the city. Whether you are interested in soul searching, bird watching, skinny dipping, or exploring the many offerings of the local area, you will discover why it’s aptly named Paradise Pines. A well equipped kitchen and an outdoor grill will meet your needs. Swim in the heated pool underneath a canopy of pine trees and keep cool for an outdoor dining experience behind mosquito curtains.

Top guest favorite
Large windows frame serene views of tall pine trees and the calm surface of Lake Jean, allowing natural light to fill the space. Wooden beams overhead enhance the rustic charm, while ceiling fans offer comfort in the warm cabin atmosphere.
Cabin in La Grange
4.94 out of 5 average rating, 251 reviews

Log Cabin Antique Week Retreat, serene lake

*New Stainless Steel Appliances!* Escape the stress of the city and experience the relaxing peace and tranquility of our log cabin surrounded by tall pines with stunning views of Lake Jean. Imagine the look on the faces of your friends or family when they step out of the car and take in the calm, smooth surface of the lake through the trees. They look at you and smile, wondering where you found this place. Inside you'll know that you made the right choice.

Top guest favorite
The interior of the cabin features wooden walls with a rustic charm. Sunlight illuminates a decorative sunflower, while a framed artwork depicts horses grazing outside. White curtains gently drape over the windows, adding to the warm atmosphere.
Cabin in Paige
4.98 out of 5 average rating, 130 reviews

Peaceful Pines Country Getaway

Rustic, remodeled cabin. 1 bedroom with queen bed, living area with (2 twin beds), 2 full baths and kitchenette. Walking trails for you to enjoy! Wet creek and 1 acre pond. Outside picnic area. Catch and release fishing. Beautiful horses grazing on the property. Multiple outdoor areas to enjoy. Sitting area on back deck with pond view from cabin. Great place to unwind and get a peaceful nights rest. 38 miles to Austin city limits.

Top guest favorite
A safari tent is set on a raised wooden deck surrounded by trees, adorned with soft lighting around the perimeter. The tent features large windows offering glimpses of nature, and a pair of Adirondack chairs invites relaxation outside.
Tent in La Grange
4.99 out of 5 average rating, 151 reviews

Pinehaven Luxury Glamping

Enjoy nature in a luxurious, climate controlled setting nestled in beautiful piney woods! Our safari tent is equipped with everything you need to relax and unwind. Take a bath in the claw foot tub, enjoy a book on the front porch, and sleep peacefully in the cozy king sized bed. Pinehaven will provide you an unforgettable glamping experience! Located approximately 20 minutes from Round Top, Texas.

Top guest favorite
A quaint cottage with a welcoming front porch is surrounded by natural greenery and landscaped paths. The entrance features a red door and light-colored siding, providing a charming contrast to the outdoor space with scattered stones and plants.
Farm stay in Paige
4.99 out of 5 average rating, 194 reviews

Shady Paddock Farm-Willow House

Welcome to our little country farm! Escape the city life for a romantic get away or just some much needed down time. Willow House is privately nestled among the trees in our back paddock, allowing views of the lovely country side from the living area as well as the cozy front porch. There is also a picnic table and charcoal grill for your use.

Popular amenities for Winchester vacation rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Fayette County
  5. Winchester