Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite

Two deer graze near a tranquil pond, with lush greenery surrounding the area. A wooden deck is visible in the foreground, featuring a covered seating area. In the background, a deer is seen near a feeder positioned by the water's edge.

Cabin in La Grange

4.98 out of 5 average rating, 178 reviews

Angeltom Cabin:20 AcreWoods >16+hot tub+tree house

A home nestled within 20 acres of pure pine forest. Two stock ponds & a tree house + playground + hot tub + UTV+ RV ! Upon arrival, you will be greeted with a country-style rustic cabin for 8 & RV for 8 , > 16 guests! She - shed with jacuzzi/spa for 5 . Eclectic stuff surrounding it ! 12 miles N. of La Grange; 90 min. away from Houston, Austin, or San Antonio. 25 min.away fromRound Top Antique Show Close enough to the city, yet private & peaceful. Enjoy a slice of country life & nature!

Top guest favorite

A cottage exterior is presented with a welcoming porch featuring two metal chairs and a small round table. A star decoration is mounted on the wall beside the door. Lush greenery surrounds the area, enhancing the inviting entrance.

Guesthouse in Smithville

4.94 out of 5 average rating, 336 reviews

Cottage w/ Pool in Historic Downtown

Smithville is a quaint, thriving city with a very relaxing feel. It has numerous outdoor activities within 30 minutes if you enjoy hiking, canoe/kayaking, biking, fishing, etc. The cottage is within walking distance to downtown restaurants and shops. The town offers many great boutiques and antique stores. The cottage is a block from famous homes featured in the movies, Hope Floats and The Tree of Life. You can see the Hope Floats house from the porch! Come unwind and enjoy the small-town life!

Top guest favorite

A spacious room features a large bed with neutral bedding and decorative pillows, accompanied by a vintage wooden table and chairs. A comfortable seating area includes a white chair and small table, while large windows provide natural light, framed with light curtains.

Guesthouse in Smithville

4.98 out of 5 average rating, 456 reviews

SMITHVILLE GUEST HAUS

Welcome to Smithville Guest Haus in Small Town USA! Only 1 block from Main Street featuring shops, restaurants and night life. Close to Round Top/Warrenton, Austin and Circuit of Americas. Take a stroll in town or spend a day in the country seeking out a treasured antique. However you choose to spend your day, know that you will RELAX IN COMFORT at Smithville Guest Haus. We can't wait to have you as our guest(s)! Health and safety are a priority for our guests!! Your hosts, Rob and Sharon

Guest favorite

A cozy studio space is shown, featuring a comfortable seating area with a dark sofa and a light coffee table. The kitchen is equipped with an oven and small appliances, while wooden accents and wall art add warmth. A small dining table and chairs are also visible.

Apartment in Smithville

4.9 out of 5 average rating, 352 reviews

Bishop Carriage House

Your own cozy hide away in historic downtown Smithville, Texas. Private parking and balcony that is on local parade route, where you can enjoy the cool evenings. Complete kitchen with, full size frig and stove and all you will need to cook a meal. Great restaurants and shops within walking distance. Queen size bed and a full size sofa pull-out with upgraded mattress. WiFi and work space. Let’s not forget a coffee station. We do allow pets, but there is a pet fee. Please included at reservation.

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

5 out of 5 average rating, 103 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 serene pond reflects the surrounding trees and the home, creating a peaceful atmosphere. Lush greenery and open space are present on the property, complemented by a clear blue sky above.

Home in Smithville

4.96 out of 5 average rating, 191 reviews

Private Fishing Spot, Family Fun & Wifi - 10 Acres

La Puerta Pink Casita invites you to come savor the quietness and beauty of the countryside in a fully furnished 2 bed/2 bath home. Spend time reminiscing, reconnecting and reenergizing with friends, family or dog(s) by the fire, making s'mores. Need wifi? We have Starlink wifi for checking email or Netflix. Enjoy 10 acres of land while sitting in the backyard. The summer heat did not dry the pond and the bass and catfish are thriving! Bring fishing poles and enjoy time by the pond.

Top 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, 112 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 exterior is framed by lush greenery, showcasing a front porch with inviting seating. The building features a gabled roof and wooden accents, while a garden area displays colorful flowers and landscaping stones, contributing to the natural surroundings.

Cottage in Smithville

5 out of 5 average rating, 159 reviews

Domovina Ranch Cottages ("The Hemingway")

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, 268 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

The exterior of a newly built modern cabin is featured, showcasing a wooden facade and a welcoming front porch. Large windows provide natural light, while steps lead up to the entrance. Surrounding trees and a landscaped yard enhance the serene outdoor setting.

Home in La Grange

4.98 out of 5 average rating, 130 reviews

The Modern Mule - Relaxing & stylish cabin escape!

Come getaway from the hustle and bustle of city life in this newly built modern cabin. 360 degree views of nature from every window and nestled away on over 10 acres, you and your guests will get the peace and quiet you’re looking for. Sit out on the deck and soak up the sun surrounded by an array of beautiful trees. Just minutes outside of La Grange where you will find charming shops, local eats and a perfect place to stay for The Ice Plant Bldg and Round Top Antique fair.

Guest favorite

The exterior of a rustic red barn-style building is set against a backdrop of trees. A wooden staircase leads to a second-story entrance, while a stone pathway winds through a landscaped area with dark mulch. A small seating area with a table and chairs is visible.

Guesthouse in Smithville

4.95 out of 5 average rating, 207 reviews

Red Rooster Barn

Welcome! Cozy rustic upstairs studio apartment in a renovated 100 year old barn with everything you will need. It is located within Historic Smithville on a beautiful 1/2 acre lot. The perfect place to escape and relax and enjoy time in small town Texas. While in Smithville you can shop the antique stores or dine in one of the many great restaurants. It is within 30 minutes of Circuit of The Americas, ABI Airport and shopping in Round Top. See you soon!

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, 125 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.