Holiday houses in Shepherd

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Top-rated holiday rentals in Shepherd

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Superhost

A cozy cabin sits nestled among trees, featuring a wooden exterior with a green roof. A spacious deck with steps leads to the entrance, while a gravel pathway provides access to an outdoor storage area. The serene lakeshore is visible beyond the tree line.

Cottage in Cleveland

4.88 out of 5 average rating, 104 reviews

Rustic cabin on the Lake

Experience the tranquil beauty of a lakeshore when you stay in this cozy vacation rental. Featuring a stunning rustic and chic interior. This tiny cabin is a must stay. Spend time fishing from the private floating dock, watching wildlife or gathering outside at the firepit with your loved ones. Full RV hook-up. Enjoy a fun filled day at one of the 3 area pools, splash pad with your kids, playground, mini golf or riverfront beach. The white sand beach on the Trinity River is only 5 minutes away.

Guest favourite

The exterior of a charming cottage is surrounded by lush greenery and tall trees. A spacious front porch invites relaxation, while a stone chimney adds character to the roofline. A second structure is visible in the background, enhancing the serene, wooded atmosphere.

Cottage in Coldspring

4.82 out of 5 average rating, 118 reviews

Bavarian Lake Cottage - Kayaks/Lake access/Hot tub

Come enjoy our German inspired cottage at Lake Livingston! It features two kitchens, 3 Bedrooms + loft, cozy living areas & relaxing outdoor private spaces with a new hot tub to enjoy the beautiful woods surrounding the lake. There's so much to do outdoors from grilling, hanging out, hiking, fishing, kayaking, picnics & water fun. Our cottage is the perfect launching spot with lake access just around the corner or for exploring all things outdoors. Quiet and serene double lot and neighborhood.

Guest favourite

A spacious home is presented, set against a backdrop of tall trees. The exterior showcases a large, inviting porch with seating. A well-maintained lawn surrounds the house, enhancing the overall privacy of the property. Natural beauty is evident in the surrounding landscape.

Home in Livingston

4.81 out of 5 average rating, 176 reviews

Little House on the Corner

Tastefully decorated home just 8 minutes from Livingston in the back of a quiet subdivision with natural privacy. Beautifully landscaped, well kept yard. Outdoor gathering areas. Finished concrete flooring. The many windows allow for beautiful natural light. Central air and heat as well as a fireplace. Fiber optic WiFi along with flat screen TVs equipped with Netflix and other apps. Spacious kitchen equipped with double sink and dishwasher. Ice maker in freezer with space to store your items.

Top Guest favourite

The rustic exterior of the bungalow is highlighted by warm string lights, providing a cozy glow as evening descends. The porch features seating arrangements, creating an inviting spot for relaxation. A large yard surrounds the structure, with old barn structures visible in the background.

Barn in Coldspring

4.94 out of 5 average rating, 35 reviews

The Barn Studio

You won’t forget the peaceful surroundings of this town and country destination. The cleverly constructed bungalow is tucked into the original tack room and feed room at one end of the 125 year old barn. Original wood walls and beams beautifully blend the old and the new. 75 private acres with wooded creek and bluff trails are highlights of this gem. The Barn decor, comfort, and convenience make for a peaceful, carefree, and inspiring retreat. Bring your horses…lots of room to ride!

Superhost

A two-story treehouse features a vibrant turquoise exterior, surrounded by lush greenery. A wooden deck extends around the structure, showcasing a separate sink area and a small table. Large windows allow natural light into the spaces, enhancing the connection with the outdoors.

Treehouse in Shepherd

5 out of 5 average rating, 19 reviews

Treehouse with golf cart- near lake

PLEASE READ CAREFULLY Escape from the city in this charming two-story treehouse in Shepherd, TX Enjoy a peaceful stay with a private entrance. ✨Features & Amenities: •Golf cart included •Sleeps 4-5 guests (sofa bed available) •Elevator (for guests unable to use stairs) •Homemade soaps included •Optional sourdough bread •fresh natural chicken eggs 🌿Explore the Area: Texas grill & caffe Sam Houston national forest 18m 5 minutes drive lake in golf cart to spot wild 🐊 alligator

Superhost

The bedroom features a queen-sized bed with an iron frame, layered with a light-colored quilt and decorative pillows. Flanking the bed are two wooden nightstands with lamps. A large window provides natural light, revealing views of the surrounding forest.

Apartment in Livingston

4.88 out of 5 average rating, 128 reviews

The Apartment at Grateful Gulley

Quiet and restful, our hide-away apartment is the perfect getaway if you are looking for a place to relax, unwind, and recharge! Nestled into six acres of private forested land, this apartment has everything you need for the perfect stay, including a deck overlooking the forest and property, a desk and work area, spacious living room, and queen-sized bedroom. Local activities, Livingston Lake, the Sam Houston Wine Trail, and quaint downtown, are all within a few miles drive.

Guest favourite

A tiny home is depicted with a blue exterior and white trim, featuring a welcoming front porch. Steps lead up to the entrance, framed by greenery and wildflowers in the foreground. Tall trees surround the property, enhancing its private setting.

Tiny home in Willis

4.91 out of 5 average rating, 154 reviews

Bluebonnet ~Quiet Retreat~ HotTub & Dog Friendly

The simplicity & relaxation of our premium 399 Sq. Ft. tiny home is so refreshing and unique. This home sleeps four. It has a Queen size bed and a luxury pullout Queen sofa. The fully equipped kitchen is perfect to fix up your gourmet meals. The Bluebonnet is nestled beside our glistening 1/2 acre pond with ducks, fish and a fountain. A wooded area behind and open fields out front brings a nice breeze across the porch. Makes for a perfect place to enjoy the Big Texas Sky!

Top Guest favourite

Farm stay in Cleveland

4.97 out of 5 average rating, 114 reviews

Pine Island Farms

My place is close to Nothing, We are located nine miles east of Conroe Tx in Montgomery county, near the Sam Houston National forest. If you are looking to relax, need a little peace and quiet, take the kids on a weekend outing, or just need a nice clean place to stay in the area then Pine Island Farm is for you. . You’ll love our place because of the outdoors space is spectacular, quiet, serene. If you love the outdoors and animals you will love Pine Island Farms.

Guest favourite

The exterior of a charming cottage is showcased, featuring a covered front porch with a welcoming entrance. The pathway leads to the white door, complemented by decorative elements at the entrance. Lush green grass surrounds the house, adding to the overall inviting setting.

Home in Shepherd

4.92 out of 5 average rating, 12 reviews

The Green Cottage

Welcome to your peaceful retreat in Shepherd, TX. Enjoy this newly renovated 2 BR cottage nestled in a quiet neighborhood. This home offers modern decor, lots of natural light and a cozy environment that will make you feel right at home. Ample parking space is available in the driveway so bring your truck and your boat! This home is just 10 minutes from Lake Livingston so you can easily enjoy a day on the water. Book today to enjoy this peaceful retreat.

Top Guest favourite

An outdoor seating area features two orange chairs placed on a wooden deck. A small side table with a decorative plant is positioned between them. The entrance door, framed by a welcoming wreath, is located in the background. A black and white geometric rug lies underfoot.

Home in Coldspring

4.95 out of 5 average rating, 107 reviews

Coldspring's Cute Cottage - Relaxing Getaway

Our country yet modern designed home is located 2 minutes from the heart of Coldspring and roughly 5 minutes from Lake Livingston. Whether you're visiting our small rural town to hike the trails of Sam Houston National Forest, hanging out on Lake Livingston, or simply looking to relax, our home is the perfect place for you. You’ll have quick and easy access to everything Coldspring has to offer, along with peace and tranquility.

Guest favourite

A spacious hot tub sits on a patio surrounded by tall trees, showcasing a clear blue sky above. The modern cabin structure features large glass doors that open to the outdoors, with seating areas visible nearby.

Cabin in Montgomery

4.97 out of 5 average rating, 117 reviews

Luxury Cabin with private hot tub (Pinos)

Escape the chaos of urban life and embrace the serenity of the forest at Stay in Babia, our exclusive cabins near Houston. This scenic 9-acre retreat is in the heart of the Sam Houston National Forest, adjacent to Lake Conroe and within walking distance of the Sam Houston multi-use trails. Our A-frame cabins blend comfort, functionality, privacy, and elegance, offering a unique glamping experience with top-notch amenities.

Guest favourite

The open-concept living area features wooden flooring and a welcoming atmosphere. Comfortable seating includes a brown leather couch and armchair around a wooden coffee table. A dining area with four chairs is visible, alongside a fully equipped kitchen with green cabinetry and stainless-steel appliances.

Home in Cleveland

4.89 out of 5 average rating, 9 reviews

Rustic Retreat - Near Houston TX

Spacious 3-bed, 2-bath rustic retreat on a private acre just 45 mins from Houston. Features wood floors, wood ceilings, a fully stocked chef’s kitchen, and a large covered back porch. Peaceful fenced backyard—perfect for relaxing or bringing your pet along. Cabin-style charm with modern comfort, near state park trails and outdoor fun. Ideal for families, couples, or remote work stays. Pet-friendly and full of Texas charm!