Winona Holiday Rentals

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Holiday Rentals in Winona

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 AU$245
includes taxes & fees
12 Oct - 13 Oct
Relaxing Country Stay with Events Welcome!

Cora's Cabins

3.0 star property
9.4 out of 10, Exceptional, (153)
"Enjoyed the stay "
The price is AU$219
includes taxes & fees
15 Oct - 16 Oct
Cora's Cabins

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

10.0 out of 10, Exceptional, (243)
"Loved the beautiful neighborhood with the tall trees! Loved having a private dock with an easy way to get in the lake and swim! Such a nice experience overall!"
HIDEAWAY at HAWKINS!East TX LAKEFRONT Cabin in the Trees-Firepit-Private dock🐟

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

10.0 out of 10, Exceptional, (31)
"Comfortable and relaxing place to stay. "
THE FAIRWAY: Modern 3BR with beautiful golf course views and convenient location

Charming and Historic Holly Cottage Carriage House in Downtown Tyler

2.0 star property
9.8 out of 10, Exceptional, (23)
"Esther was great with communication and the carriage house was elegant and comfortable with everything we needed. The place was very clean and we had a great stay."
The price is AU$225
includes taxes & fees
2 Oct - 3 Oct
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Willow's Cabin - Cozy Cabin Nestled In The Woods

10.0 out of 10, Exceptional, (87)
"This property is perfect if you are looking for a place for peace and quiet. We were looking for a place in a natural setting to go to recover from a stressful lifestyle."
Willow's Cabin - Cozy Cabin Nestled In The Woods

A 1921 Craftsman with Charm in Tyler!

10.0 out of 10, Exceptional, (3)
"A truly exceptional stay! The location in the safe and central Azalea district is perfect. The home is beautiful and spotless, with every detail perfected. The host is caring and highly responsive, making us feel instantly at home. Bonus: convenient carport parking. I liked it so much I immediately rebooked and look forward to my return. "
The price is AU$381
includes taxes & fees
5 Oct - 6 Oct
A 1921 Craftsman with Charm in Tyler!

Vintage Cottage on Lake!<br>Fish Camp Cabin<br>FREE kayak, canoe & bike use!<br>

10.0 out of 10, Exceptional, (233)
"The home was wonderful. "
Vintage Cottage on Lake!<br>Fish Camp Cabin<br>FREE kayak, canoe & bike use!<br>

Cozy 2 bedroom 2 bath duplex near UT Tyler!

9.8 out of 10, Exceptional, (35)
"Host was wonderful. Clean play and a perfect place to stay for our trip."
The price is AU$310
includes taxes & fees
5 Oct - 6 Oct
Cozy 2 bedroom 2 bath duplex near UT Tyler!

The Cottage at Dogwood Ridge.

10.0 out of 10, Exceptional, (106)
"Comfortable, clean, good location, friendly hosts! "
The price is AU$258
includes taxes & fees
2 Oct - 3 Oct
The Cottage at Dogwood Ridge.

Luxury Log Cabin in the Premier Resort-Holly Lake Ranch

9.6 out of 10, Exceptional, (161)
"Awesome place and awesome host. Communicates well and goes the extra mile to make sure we have a great stay. Highly recommend "
Luxury Log Cabin in the Premier Resort-Holly Lake Ranch

6 BR Log Home in Piney Woods of East TX with hot tub and POND

10.0 out of 10, Exceptional, (37)
"We had a great stay! Home was very clean and comfortable. Plenty of room for the family with lost of fun stuff for the kids and teens. Host was very friendly. We will come back!!"
6 BR Log Home in Piney Woods of East TX with hot tub and POND

The Carriage House, The Carriage House at Jeter Farmhouse

9.6 out of 10, Exceptional, (4)
"Cousin Becky and i had a great time exploring a small country town known for their antiques. Location of guest house is spot on.Quite with all the amenities. Thanks Brad and Kristi"
The price is AU$208
includes taxes & fees
22 Oct - 23 Oct
The Carriage House, The Carriage House at Jeter Farmhouse

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

9.8 out of 10, Exceptional, (111)
"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!

STAY TYLER @ Vine- near shops- Fast Wifi

10.0 out of 10, Exceptional, (53)
"Very clean and had everything we needed for our quick overnight trip."
The price is AU$462
includes taxes & fees
2 Oct - 3 Oct
STAY TYLER @ Vine- near shops- Fast Wifi

Cana Cottage | Farm Stay

10.0 out of 10, Exceptional, (35)
"Perfect for my daughter’s wedding night. Super close to the venue. "
The price is AU$188
includes taxes & fees
5 Oct - 6 Oct
Cana Cottage | Farm Stay

City Zen: Modern Country Retreat

10.0 out of 10, Exceptional, (13)
"We stayed here on while in the process of moving across the country. The house was beautiful and had a huge back yard!"
The price is AU$626
includes taxes & fees
5 Oct - 6 Oct
City Zen: Modern Country Retreat

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

10.0 out of 10, Exceptional, (90)
"Had a blast at our annual HLR family reunion. Magnolia was exactly as described, and in a perfect location "
Magnolia Pines @ Holly Lake Ranch +++++ Bunkhouse Addition Available

Enjoy 1.3 wooded acres and location to amenities Holly Lake has to offer.

10.0 out of 10, Exceptional, (24)
"The home and area is very beautiful and clean."
Enjoy 1.3 wooded acres and location to amenities Holly Lake has to offer.

Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views

10.0 out of 10, Exceptional, (3)
"The home is beautiful and in an amazing location it was very clean and Julie is an amazing host and she responded so quickly to any questions "
The price is AU$484
includes taxes & fees
2 Oct - 3 Oct
Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views
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

Find out more about Winona

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

THE FAIRWAY: Modern 3BR with beautiful golf course views and convenient location: This holiday home rental outside of Winona offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 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 Pine Springs Golf Course 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.