Holiday rentals in Winona

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Top-rated holiday rentals in Winona

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Top guest favourite
The exterior of the main house is shown, featuring a white facade with a sloped roof and large glass doors. Surrounded by lush greenery, the spacious lawn provides ample outdoor space for relaxation. A patio area with seating enhances the tranquil setting.
Farm stay in Winona
4.94 out of 5 average rating, 18 reviews

Pine Hill Farm, House and Guest House

Enjoy the sounds of nature while staying at this peaceful farm near Tyler on 35 acres with a private lake, main house, guest house, boat dock and multiple outdoor entertaining areas. A total of 4 bedrooms and 3 full baths, 2 kitchens, multiple living and dining areas. This gated , private compound is a perfect place for large family gatherings. Explore nature, fish from the dock, sit by the fire pit, play games, read and relax! Close to Tyler and Lindale. Inquire about fees for event rental.

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, 273 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

Guest favourite
A cozy sleeping area is presented with a dark wooden bed frame and an assortment of pillows. A gray blanket is draped over the bed, and a bedside table holds a lamp, providing soft light. Nature-themed artwork adorns the wall above the bed.
Tiny home in Tyler
4.9 out of 5 average rating, 88 reviews

Crystal's Cabin

Reconnect with nature at this unforgettable escape. Beautiful country charm but only minutes from town! Cozy cabin offers everything you need to unplug from busy schedules and work; no TV or WiFi. Nice farm feel as animals graze. Bring your fishing gear! We offer catch & release fishing from the beautiful pond on the property. Or sit and enjoy the beauty of the pond from the gazebo! Cabin is equipped w/kitchenette complete with a coffee maker, microwave, toaster oven, single burner, & fridge.

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, 173 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

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, 121 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.

Top 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
4.97 out of 5 average rating, 151 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.

Superhost
A spacious bedroom is furnished with a memory foam queen bed dressed in soft white linens. Colorful pillows complement the blue headboard. Soft lighting from bedside lamps and a decorative shelf creates a cozy ambiance, while a mini fridge is conveniently located nearby.
Guest suite in Tyler
4.85 out of 5 average rating, 248 reviews

Your Home away from Home! Fast Internet - Fire TV

Welcome to your home away from home! A private studio space, with a private bathroom & private patio entrance. This is the back unit of an Airbnb Duplex. We strive to provide a comforting space for those on the go, so we include free small breakfasts, coffee, and teas! We are located on the interior of SW Loop 323, near Broadway and 5th street. just under 10 minutes to major hospitals, shopping, food & drinks! Check out the descriptions below!

Top guest favourite
An open-concept kitchen and dining area features a round wooden table with four chairs. Bar stools are positioned at a kitchen island, which holds modern appliances and a fruit bowl. A cozy seating area with a brown sofa is visible, complemented by wooden accents and a high ceiling.
Cabin in Lindale
4.95 out of 5 average rating, 128 reviews

The Lodge at Hidden Creek

Come relax in this newly-renovated getaway nestled in the woods of East Texas. This cozy, stylish lodge offers the seclusion you seek while still being conveniently located to restaurants and attractions with easy access to Interstate 20. You'll feel comfortable in this quaint cabin which features a large kitchen, king-sized bed, high speed internet, outdoor fire pit, and is stocked with all the necessities.

Top guest favourite
A cozy living area showcases a bright blue sectional sofa and a pair of dark blue armchairs. A round coffee table with a gold finish sits in the center, surrounded by a plush area rug. Floor lamps provide soft lighting, enhancing the inviting atmosphere.
Guest house in Longview
4.96 out of 5 average rating, 333 reviews

Glamping Cabin - Boho Retreat

Forget your worries in this spacious and serene wooded area of the piney woods of East Texas. Unwind, relax and enjoy a glass of wine on our deck overlooking the canopy of trees. 1 Queen Bed. 2 twin pullout couches. Coffee available in cabin. Microwave and fridge on site. Bottles of wine available for purchase. Need any extra accommodations? Just ask! I will do what I can to make it possible.

Top guest favourite
The exterior of a quaint garage apartment is visible, featuring a light-colored facade with brown trim. A single garage door is situated below, flanked by greenery and flowering plants, enhancing the inviting entrance under a clear blue sky.
Guest house in Tyler
4.99 out of 5 average rating, 202 reviews

Brick Street Bungalow Garage Apartment

The Brick Street Bungalow is a quaint, cozy studio apartment above our garage located on the brick streets in the Azalea District. You will be within blocks (walking distance) of Bergfeld Park, The Children’s Park, a local coffee shop in The Brick Street Village and one mile from downtown and the hospitals. We offer discounts for weekly and monthly guests.

Top guest favourite
A well-appointed bedroom features a Queen bed with an elegant headboard, complemented by decorative pillows. A cozy seating arrangement includes a tufted loveseat and a traditional chair. Natural light filters through two window treatments, enhancing the warm tones of the hardwood floor and classic furnishings.
Place to stay in Tyler
4.99 out of 5 average rating, 267 reviews

Quiet, cozy, in the Azalea district

We are a retired couple with a beautiful home in the Azalea district of Tyler, Texas. We are less than half mile to both hospitals. Two blocks from Bergfield Park. Close to both Colleges. Close to shopping areas. Many great restaurants close to area. We welcome you to our home where you will find privacy, quietness, and a relaxing atmosphere.

Top guest favourite
A bright sleeping area features a queen-sized bed with white linens accented by a tan blanket. Two bedside tables with lamps flank the bed. A large window allows natural light to fill the space, while neutral tones create a calming atmosphere.
Tiny home in Tyler
4.99 out of 5 average rating, 164 reviews

Tiny House in the Country

Welcome to this tiny home in the country located on twenty-three acres of woods and pasture. You will be able to enjoy the beauty of the outdoors while still having access to places of interest. You are only: 8.8 miles from Lindale 15 miles from Tyler 15 miles from Tyler State Park 27 miles from Canton Trade Days Current WiFi is not high speed.

Popular amenities for Winona holiday rentals

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