Holiday houses in Winona

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Top-rated holiday rentals in Winona

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

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Top Guest favourite
A single-story brick house is situated on a quiet street, framed by lush greenery. The driveway leads to a double garage, while a mailbox stands at the edge of the property. A flag gently flutters from the front porch, enhancing the home’s welcoming appearance.
Home in Lindale
5 out of 5 average rating, 178 reviews

The Rita House

Centrally located in Lindale, yet back off a quiet street with a peaceful, fenced backyard with driveway parking. Up to 2 well-behaved pets are welcome! (Prior approval needed for more). It’s a quick walk to "The Cannery" which hosts Miranda Lambert's Pink Pistol and Red 55 Winery as well as Texas Music City Grill. Beautiful Darden Park and nearby dog park are also walking distance. It's also just a short drive to the quaint town of Mineola, the Texas Rose Horse Park and Canton First Mondays.

Top Guest favourite
A charming black house is nestled among towering trees in a wooded setting, featuring a spacious deck that wraps around two sides. Natural light filters through the foliage, creating a serene atmosphere that invites relaxation and connection with nature.
Cabin in Tyler
4.95 out of 5 average rating, 315 reviews

The Hygge House - Respite in the forest

Escape into nature and experience the warm embrace of hygge (HYOO-gah) - a Danish word that describes a deep feeling of well-being. Nestled in a tranquil natural setting, our home is a sanctuary for slow living, rest, and fostering connection. The soft furnishings and natural light make this the perfect place to savor some of the simple pleasures of life - fresh baked cookies, a nap in our oversized deck hammock and meaningful conversation. Our hope is that you leave renewed. 12mi to Downtown

Top Guest favourite
The exterior of Willow's Cabin features a rustic log construction, warmly lit by porch lights. The wraparound porch is furnished with rocking chairs, inviting relaxation amid the surrounding trees. Steps lead up to the entrance, highlighting the cabin's welcoming atmosphere.
Cabin in Gilmer
4.98 out of 5 average rating, 283 reviews

Willow’s Cabin - A Cozy Little Cabin Nestled In The Woods

Willow’s Cabin provides the absolute getaway opportunity where peace and quiet gives you the sounds of nature while receiving the best feel at home experience we can offer! We’re far enough from the big cities yet close enough to all of the amenities our towns offer such as restaurants, shopping malls, cinemas, historic parks and large grocery stores. All proceeds go to our nonprofit, Oinkin Oasis Forever Home potbelly pig sanctuary AND are tax deductible!!! Parking/premise for guest only.

Superhost
A cozy outdoor space features a fire pit with a roaring flame, a picnic table, and a lantern on a gravel surface. The rustic cabin, framed by towering pine trees, is illuminated softly by an exterior light, enhancing the serene atmosphere.
Cabin in Winona
4.92 out of 5 average rating, 194 reviews

Tranquil Cabins Studio-East Texas Pines-near Tyler

Tranquil Cabins Studios are in the piney woods in Winona, TX, near Tyler, just 2 hours from DFW. Handcrafted tiny cabins inspired by nature: -Huge picture windows that immerse you in nature. -Cozy Qbed w/ cotton linens -Kitchenette w/ induction stove, mini-fridge/freezer, & utensils. -Private bath w/ hot shower, toilet & towels. Private outdoor space, w/ fire pit, chairs, & picnic table. Perfect for a romantic escape, solo retreat, or working in nature. *Wi-Fi is not for streaming

Guest favourite
A spacious seating area features a black leather sofa with contrasting orange cushions, alongside a light-colored armchair. A low wooden coffee table is placed on a textured rug. Large windows allow natural light to fill the space, complemented by indoor plants and exposed concrete walls.
Loft in Downtown Tyler
4.96 out of 5 average rating, 558 reviews

Downtown Rose Capital Studio w/ Private Sauna

The Rose Capital Studio is a unique and inspiring space. Rose Capital Studio features a 9ft wide ceiling-mounted 'backdrop' and movie projector which is perfect for entertainment. The space includes beautiful large windows, exposed concrete beams, and a private sauna for relaxation. As impressive as the space is, the best feature is likely our location. The studio is located right in the middle of Downtown - in walking distance from so many of Tyler’s best coffee-shops, restaurants, & bars.

Top Guest favourite
An inviting deck showcases a combination of conversation lounge furniture and a bar dining set. The A-frame cabin's wooden exterior is complemented by large glass doors and windows, allowing natural light to fill the space. Surrounding trees add a serene backdrop.
Place to stay in Tyler
4.99 out of 5 average rating, 135 reviews

Piney Point A-Frame Retreat Tyler

Created to share the uniqueness of East Texas with others, Piney Point is a perfect couple or friend's retreat. Tucked in the corner of a six-acre homestead, this restored A-frame offers a modern cozy stay with an expansive deck that overlooks the spring-fed pond. Nearby are some of the best adventures East Texas has to offer, from hiking trails and fishing at Tyler State park, live music, downtown breweries, to market shopping and great food. Escape to the quiet to rest and recharge.

Guest favourite
A modern tiny home is shown, featuring a charming white exterior with black trim and a dark roof. The front porch area includes a small bench, surrounded by green grass and blooming flowers. Large windows allow natural light to fill the space.
Farm stay in Winona
4.95 out of 5 average rating, 159 reviews

Lily's Pad Peaceful stay and events welcome!

Kick back and relax in this calm, stylish space. This tiny home was built in 2022. Sitting on almost 5 acres with a pond, this place is the meaning of relaxing! Enjoy your time with a beautiful view, and unwinding from the business of the outside world. There are many choices for dining, entertainment and shopping within a few minutes drive! If you are looking to book an event, please go into the house rules and under additional rules are the terms and agreement for booking events.

Top Guest favourite
The treehouse is illuminated softly against a darkening sky, perched among the trees. Its wooden structure features a spacious balcony, supported by sturdy tree trunks. The surrounding area is lined with foliage, contributing to a secluded, peaceful ambiance.
Treehouse in Lindale
4.95 out of 5 average rating, 281 reviews

Moon Honey Treehouse - Romantic Getaway - No Kids

Gorgeous treehouse escape nestled in the tree tops of Garden Valley, Tx. The perfect place for a honeymoon, anniversary or surprise romantic getaway! All the joy and imagination of a treehouse combined with elegance, modernized to help adults relax and reconnect. Enjoy coffee in the trees on the balcony, wine and cheese with a sunset view, indoor/outdoor shower. Fully stocked kitchen and outdoor hibachi grill for those who love to cook, great local restaurants for those who don’t.

Top Guest favourite
A charming two-story house is surrounded by vibrant flower beds and well-maintained landscaping. A spacious patio greets guests, featuring a bar area and decorative lighting. The gravel pathway leads to the entrance, showcasing a welcoming atmosphere amidst lush greenery.
Home in Gladewater
4.99 out of 5 average rating, 162 reviews

Rural Paradise, Fishing, Games, Seclusion

Message us to find out about 3 day weekend discounts! 10 minutes off Interstate 20. Bring friends & family! Find a "My Space" & chill. There's lots! Cook some stuff! No close neighbors. All bedrooms have T.V.! The pergola swing is a great place to enjoy a private waterfront view! Lots of coffee & tea! Stocked pantry w free & avail/purchase snacks & drinks! FULL kitchen inside & outside too! Make a milk shake! Take a walk, cook, eat, yard games, or go fishing - GO AMERICANA!

Superhost
A private hot tub sits on the spacious deck of the cottage, surrounded by trees. The exterior includes a welcoming red door and a comfortable seating area with chairs. Natural light filters in through the windows, enhancing the outdoor living space.
Cottage in Lindale
4.92 out of 5 average rating, 401 reviews

The Cottage at Hidden Creek w/ Hot Tub and Firepit

Quaint cottage nestled among three acres of towering trees. Featuring a large, newly updated kitchen, spacious bedroom, and lots of outdoor living space including a hot tub and fire pit. This cabin in the woods offers the seclusion and East Texas beauty you seek, yet is just minutes away from numerous restaurants and attractions with easy access to Interstate 20 and Toll 49. Retreat to the large deck and gaze at the stars, or grab a blanket and enjoy s’mores by the fire.

Top Guest favourite
A front porch is depicted, featuring two red chairs and a small round table. The entrance is framed by white columns and includes a welcoming white door. A decorative sign reading 'HOME' adds a personal touch, while light filters in through the windows.
Cottage in Mineola
4.97 out of 5 average rating, 140 reviews

Grannie's Guest House

My place is 6 miles east of Mineola, TX. Close to antique shopping, Mineola nature preserve, public lakes, 30 minutes to Canton First Monday trades days, and many other spotlights in East Texas. You’ll love my place because of the cozy, farmhouse atmosphere and country living. My place is good for couples, solo adventurers, and business travelers. Not suitable for kids or children, and I do not allow pets or animals of any kind on the property.

Guest favourite
A firepit area is surrounded by four adirondack chairs, two in black and two in blue, positioned on sandy ground. The tranquil waters of Lake Hawkins reflect the soft pastel hues of the sunset, with a boat dock and gazebo visible in the background.
Cottage in Hawkins
4.89 out of 5 average rating, 108 reviews

Lakehouse - Sleeps 6, Dock, Fire Pit, Kayaks

Welcome to GRIF's GETAWAY. A cozy fully renovated vintage cottage on Lake Hawkins. Enjoy 2 bedrooms with antique queen beds, a 4-pc bath, and a queen sleeper sofa in the living room. Relax with vintage linens, plenty of closet space, and modern comforts. Outside, take advantage of the private dock, firepit, and 2 kayaks. Nestled among trees with tranquil lake views-perfect for a weekend escape or longer retreat!

Popular amenities for Winona holiday rentals

  1. Airbnb
  2. United States
  3. Texas
  4. Smith County
  5. Winona