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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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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, 300 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, 277 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
4.91 out of 5 average rating, 188 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, 555 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, 130 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, 158 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.

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, 275 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
The private boat dock extends into the calm lake, featuring a covered area with a table. Reflections of the structure and surrounding greenery can be seen in the water, while fluffy clouds drift overhead against a blue sky.
Cottage in Winnsboro
4.95 out of 5 average rating, 301 reviews

Wild Ducks Cottage on Lake Winnsboro

Shaded A-frame with sunrise/moonrise views. Great get-away cottage for rest, relaxation & fishing. Dock, open deck, screened deck. Covered parking, paved driveway. Lake access for boat. Wood County HOTax & cleaning fee included in nightly rate. Ltd. TV stations. DVD player. Near vibrant Winnsboro for shopping, Saturday morning Farmers Market, dining, coffee, food trucks, Finders Keepers, Winnsboro Center for the Arts, Autumn Trails, Art & Wine Festival, Book Fair, Bloom, Rodeo.

Top Guest favourite
A view from the hot tub shows the cottage in the background, surrounded by trees and soft lighting from patio strings. The focus is on the bubbling water of the hot tub, promoting relaxation and an outdoor ambiance.
Cabin in Como
5 out of 5 average rating, 125 reviews

A Little Countryside Paradise

Maybe I'm a little partial, but I really have to pinch myself when I go visit Callie's cottage. Imagine...a beautiful country road, quiet except for the occasional sound of a cow. A cottage tucked into an abundance of trees, wrap around porch, flagstone firepit area, patio lights strung across the yard, antique mantle with gas fire, crystal chandelier, beadboard from an 1800's farmhouse, a tub big enough for two, the lushest bedding, classical music plays, sweets served. Deep sigh.

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, 395 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.

Guest favourite
A treehouse is illuminated at dusk, highlighting its elevated porch with wooden railings and steps leading up. Surrounding greenery adds a natural frame, while soft lighting from within suggests warmth and comfort in the inviting space.
Treehouse in Lone Oak
4.96 out of 5 average rating, 218 reviews

Nature’s Hideaway - The Urban Treehouse

Feeling inspired to have a holiday experience that will leave you absolutely refreshed; look no further. Nestled into the woods, this stunning treehouse is where nature meets modern design. Created with an inspired state of mind, you won’t have to sacrifice comfort to embrace the quiet of the off beaten path. Unwind by the fireside, absorbing the sound of the crackling of the wood, gaze at the stars overhead, and welcome the tranquility all around.

Guest favourite
A spacious living room is highlighted by a large dark leather couch adorned with white and blue pillows. A small dog sits comfortably on the couch, surrounded by two warm lamps on side tables. Decorative plants and artwork are visible in the background, creating an inviting space.
Home in Tyler
4.94 out of 5 average rating, 253 reviews

Beautiful new home near the Tyler Airport

Bring the whole family, including the family pet (no pet fees), to this beautiful new home with lots of room to relax. This home includes a large TV in the living room for movies, games, internet and a gourmet kitchen to make meals together. Create new memories or just enjoy time together. Detailed instructions, including your Lock Code, will be shared with you after booking.

Popular amenities for Winona holiday rentals

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