Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

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, 491 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

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Top Guest favourite

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, 194 reviews

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

Nestled on 20 acres of peaceful pine forest, Angeltom Cabin & brand-new RV offers a unique Texas getaway for up to 16-22 guests. Enjoy our rustic cabin, RV, 2 stock ponds, treehouse, playground, UTV, hot tub, She-Shed spa, Red Pavilion/ Barn , games, trails, & more. Everything is included for a fun, relaxing stay—just bring your food! Located 12 miles north of La Grange, 25 minutes from Round Top, & about 90 minutes from Houston, Austin, & San Antonio. Close to the city, yet private & peaceful!

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Top Guest favourite

The exterior of a historic two-story house is framed by large Magnolia and Oak trees, showcasing a classic Greek Revival design. The welcoming entrance features double doors under a portico supported by white columns, while the well-maintained lawn and pathway lead up to the front steps.

Home in Smithville

4.93 out of 5 average rating, 113 reviews

The Ella Norah, A Bespoke Luxury Retreat, Pool Spa

Welcome to The Ella Norah. A 1910 Cyprus Greek Revival that has been fully restored to modern day luxurious glory while still retaining its historic charm. Relaxing & gorgeous haven surrounded by large Magnolia & Oak trees. A bird lover's paradise.This unique place has a style all its own & is in the central historic district of quaint charming, Smithville, Texas. A fabulous place to gather with family & celebrate special occasions, all within steps of Main Street shopping & restaurants.

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Top Guest favourite

A rustic cabin exterior is presented, featuring a wooden façade and a metal roof. A porch with white Adirondack chairs invites relaxation, while a gravel path leads to an outdoor picnic table. Backyard games and a grill are visible on the expansive lawn.

Cabin in La Grange

4.95 out of 5 average rating, 132 reviews

The Rustic Retreat | 25 Acres | Cedar Cabin

Its 15 mins. to Round Top & 9 min. to La Grange. Designed for families or couples looking to relax and unplug, this quintessential La Grange cabin boasts the utmost privacy and serenity on your getaway. Once you've settled in, explore the property where you can find a serene pond, wildlife, and livestock grazing. Gather around the fire pit for s’mores and stories under the stars by night. This cabin is perfectly located near wineries & nature parks while still maintaining its remote feeling.

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Guest favourite

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, 169 reviews

Hobbit's Nest Treehouse | A Magical Forest Retreat

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.

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Top Guest favourite

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

4.97 out of 5 average rating, 232 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.

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Top Guest favourite

The exterior of the cottage features a vibrant pink front door framed by two windows with dark shutters. A small porch area with two white chairs is visible, and a decorative welcome mat is placed at the entrance. Surrounding greenery adds to the inviting atmosphere.

Cottage in Smithville

4.99 out of 5 average rating, 114 reviews

Charming Texas Cottage - Main House

Escape to the heart of Texas and experience the charm of Smithville in our cozy cottage that sleeps up to 4 guests. Nestled on a double lot, this fenced property is perfect for guests traveling with their furry friends. With a queen bed and a full bed, our cottage is ideal for couples, families, or a group of friends looking for a relaxing getaway. We also have a 1 bedroom casita on the property that is completely fenced and private. Let us know if you're interested in both properties!

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Top Guest favourite

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, 286 reviews

Best Little Cabin in Texas

Secluded cabin on 250 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 $30 per pet fee. Up to three. Please let us know if you’ll be bringing yours.

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Top Guest favourite

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

4.97 out of 5 average rating, 156 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.

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Guest favourite

A tranquil cabin is nestled among tall trees, positioned beside a calm, green-tinted pond. The wooden structure features a covered porch and is accompanied by a small dock. A basketball hoop can be seen nearby, offering outdoor recreational opportunities.

Cabin in La Grange

4.96 out of 5 average rating, 55 reviews

Piney Creek Cabin

Take a break and unwind at this peaceful oasis. Enjoy the private, quiet, peaceful cabin tucked back in the woods. Eight hundred sq ft of beautiful living space with 2 Bedrooms and 2 Full Bathrooms and a Loft. The porch is a great place to relax and take in the Beauty around you. The view from the cozy cabin is a stocked lake and dock. Fish, kayak, play basketball, enjoy a walk, The possibilities are endless. Abundant Wildlife can be found all over the property.

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Top Guest favourite

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

4.95 out of 5 average rating, 273 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.

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Top Guest favourite

A serene outdoor space is presented, featuring a sleek swimming pool surrounded by a well-manicured lawn. Lounge chairs sit invitingly at the pool's edge, complemented by gentle landscaping. A sunset sky with a mix of soft pink and blue hues enhances the tranquil atmosphere.

Home in Smithville

4.99 out of 5 average rating, 122 reviews

Colorado River Escape

Experience the ultimate Colorado River lifestyle in beautiful Smithville, Texas, just 30 minutes east of the Austin airport. In the heart of town, this property has direct frontage on the river, with panoramic views and direct access to the water. Main Street and all its shopping and dining are just one block away! "Small town, big heart" is our motto in this gem we call Smithville!

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