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Top Holiday Rentals in Winona

Our top choices for Winona holiday rentals

Relaxing Country Stay with Events Welcome!

9.8 out of 10, Exceptional, (19)
"It was very cozy and clean, me and my partner had a very comfortable stay"
The price is £121
includes taxes & fees
21 Aug - 22 Aug
Relaxing Country Stay with Events Welcome!

Cora's Cabins

3.0 star property
9.4 out of 10, Exceptional, (149)
"Enjoyed the stay "
The price is £114
includes taxes & fees
21 Aug - 22 Aug
Cora's Cabins

HIDEAWAY at HAWKINS!East TX LAKEFRONT Cabin in the Trees-Firepit-Private dock🐟

10.0 out of 10, Exceptional, (240)
"Enjoyed our stay and would recommend!!!"
HIDEAWAY at HAWKINS!East TX LAKEFRONT Cabin in the Trees-Firepit-Private dock🐟

Willow's Cabin - Cozy Cabin Nestled In The Woods

10.0 out of 10, Exceptional, (84)
"Wife and I had a great weekend. Enjoyed the cabin. Nice place to stay. "
Willow's Cabin - Cozy Cabin Nestled In The Woods

STAY TYLER @ Vine- near shops- Fast Wifi

10.0 out of 10, Exceptional, (50)
"Tge property was clean, comfortable and well stocked. We enjoyed our stay and would book again."
The price is £224
includes taxes & fees
21 Aug - 22 Aug
STAY TYLER @ Vine- near shops- Fast Wifi

Magnolia Pines @ Holly Lake Ranch +++++ Bunkhouse Addition Available

10.0 out of 10, Exceptional, (89)
"We came for a family wedding. The house was perfect for our family. We had a great time "
Magnolia Pines @ Holly Lake Ranch +++++ Bunkhouse Addition Available

Charming and Historic Holly Cottage Carriage House in Downtown Tyler

2.0 star property
9.8 out of 10, Exceptional, (19)
"Private garden was very beautiful. Host was friendly and very kind to share the garden with us."
The price is £111
includes taxes & fees
25 Aug - 26 Aug
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Cozy Cabin in Big Sandy

10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay. The cabin was very clean. The road nearby was very noisy but that can't really be helped. I would stay here again."
The price is £204
includes taxes & fees
21 Aug - 22 Aug
Cozy Cabin in Big Sandy

THE FAIRWAY: Modern 3BR with beautiful golf course views and convenient location

9.8 out of 10, Exceptional, (30)
"Comfortable and relaxing place to stay. "
THE FAIRWAY: Modern 3BR with beautiful golf course views and convenient location

Vintage Lakefront Cottage, Private Dock, Infinity Beach Pit, 2 Kayaks!

9.8 out of 10, Exceptional, (108)
"Very nice & relaxing place to stayFishing was good We will be back next yearToni was very helpful when we had questions "
Vintage Lakefront Cottage, Private Dock, Infinity Beach Pit, 2 Kayaks!

Welcome to the “The Barn”.

10.0 out of 10, Exceptional, (59)
"Took a quick girls trip. Location is close to everything. Beds were comfortable and the pool was a great perk."
Welcome to the “The Barn”.

Guesthouse on peaceful 11+ acre homestead! Pet friendly!

10.0 out of 10, Exceptional, (27)
"Our family had a great time staying here! The kids LOVED the loft, the sheep, & the livestock guardian dog Roxy! "
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Modern Azalea District Home

7.4 out of 10, Good, (3)
"Such a fun and unique property with amazing communication from the hosts! The check-in and check-out process was easy. The house was clean and in a great location. We arrived late after helping set up for an outdoor wedding all day, and the AC was wonderful. The backyard was perfect for our senior dogs to explore. I messaged the host when I could not find the coffee maker, and she delivered one to us almost immediately, which was beyond appreciated since our weekend was so busy. Absolutely...
Modern Azalea District Home

Luxury Log Cabin in the Premier Resort-Holly Lake Ranch

9.6 out of 10, Exceptional, (160)
"Cabin was cozy, location was beautiful, plenty of outdoor activities, nice amenities and wildlife was wonderful. "
Luxury Log Cabin in the Premier Resort-Holly Lake Ranch

Stay Tyler @ Villa Grande

9.8 out of 10, Exceptional, (18)
"The hosts were responsive, and the houses are lovely. Our family was celebrating two graduations and this property provided an excellent backdrop."
The price is £748
includes taxes & fees
21 Aug - 22 Aug
Stay Tyler @ Villa Grande

Spacious 1-Bedroom Guesthouse in the Woods

10.0 out of 10, Exceptional, (42)
"Really roomy and great price"
The price is £97
includes taxes & fees
21 Aug - 22 Aug
Spacious 1-Bedroom Guesthouse in the Woods

Waterfront - Enjoy The Sunset Lodge Lake House with kayaks, dock, swimming

10.0 out of 10, Exceptional, (14)
"Love it here and its so so peaceful. Its a home you can free your mind in peace."
Waterfront - Enjoy The Sunset Lodge Lake House with kayaks, dock, swimming

4-bedroom home with fitness equip. WiFi, pool table, fire pit, huge backyard

10.0 out of 10, Exceptional, (4)
"Very clean and Comfortable. Definitely a great place to stay. "
4-bedroom home with fitness equip. WiFi, pool table, fire pit, huge backyard

The Cottage at Dogwood Ridge.

10.0 out of 10, Exceptional, (104)
"Comfortable, clean, good location, friendly hosts! "
The price is £128
includes taxes & fees
21 Aug - 22 Aug
The Cottage at Dogwood Ridge.

Charming 1-bedroom Getaway in the heart of Kilgore

2.0 out of 10, (1)
"The street is small and blocked by other cars most of the day. There is a large and loud family living in the other side of house. You will not want to walk in the dark in this neighborhood. "
The price is £106
includes taxes & fees
23 Aug - 24 Aug
Charming 1-bedroom Getaway in the heart of Kilgore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winona Hotel Reviews

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Mrs. Lee's Daffodil Garden, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winona has to offer?

Magnolia Pines @ Holly Lake Ranch +++++ Bunkhouse Addition Available: This holiday home rental outside of Winona is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Caldwell Zoo, or get out into nature at a spot like Mrs. Lee's Daffodil Garden. Tyler State Park and Jarvis Christian College are a couple of places you'll find in the wider area.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.