Winona Holiday Rentals

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Holiday Rentals in Winona

Relaxing Country Stay with Events Welcome!

Winona
9.8 out of 10, Exceptional, (19)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
United States
Ray T.
The price is AU$242
includes taxes & fees
9 Dec - 10 Dec
Relaxing Country Stay with Events Welcome!

Charming and Historic Holly Cottage Carriage House in Downtown Tyler

2.0 star property
Tyler
9.8 out of 10, Exceptional, (27)
"Good location. Nice neighborhood. Parking was on the street but very little to no traffic so it was ok. The host responded quickly and was very helpful. "
United States
Patricia R.
The price is AU$232
includes taxes & fees
11 Dec - 12 Dec
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Cora's Cabins

3.0 star property
Tyler
9.4 out of 10, Exceptional, (155)
"Enjoyed the stay "
United States
Benito
The price is AU$228
includes taxes & fees
9 Dec - 10 Dec
Cora's Cabins

Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Tyler
10.0 out of 10, Exceptional, (31)
"Our family had a great time staying here! The kids LOVED the loft, the sheep, & the livestock guardian dog Roxy! "
United States
Kayla B.
The price is AU$175
includes taxes & fees
9 Dec - 10 Dec
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Grable Creek Farmhouse

Longview
9.8 out of 10, Exceptional, (41)
"Very nice stay, ac is great, easy access, exactly as represented, very helpful information, comfortable accommodations."
United States
James R.
Grable Creek Farmhouse

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

Hawkins
10.0 out of 10, Exceptional, (238)
"The home was wonderful. "
United States
Jonnie C.
Vintage Cottage on Lake!<br>Fish Camp Cabin<br>FREE kayak, canoe & bike use!<br>

Cana Cottage | Farm Stay

Tyler
10.0 out of 10, Exceptional, (43)
"Good design, well maintained "
United States
William
The price is AU$201
includes taxes & fees
8 Jan - 9 Jan 2026
Cana Cottage | Farm Stay

STAY TYLER @ Vine- near shops- Fast Wifi

Tyler
10.0 out of 10, Exceptional, (55)
"Our stay was great, clean house, and comfortable beds, perfect for a large family. The home had everything we needed. We were so glad they welcomed our pets and were not worried about pet size and weight like other homes are. I highly recommend this rental for anyone visiting Tyler. "
United States
Nanette Carpenter
The price is AU$457
includes taxes & fees
9 Dec - 10 Dec
STAY TYLER @ Vine- near shops- Fast Wifi

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

Hawkins
10.0 out of 10, Exceptional, (249)
"The house was perfect and the area really pretty. Great place to relax and enjoy life. "
United States
Michael B.
HIDEAWAY at HAWKINS!East TX LAKEFRONT Cabin in the Trees-Firepit-Private dock🐟

STAY TYLER @ Faulkner- amazing location

Tyler
10.0 out of 10, Exceptional, (31)
"Had a great stay."
United States
Edward M.
The price is AU$531
includes taxes & fees
9 Dec - 10 Dec
STAY TYLER @ Faulkner- amazing location

BestStays@Queen Bee Cozy for couples and small families

Tyler
9.0 out of 10, Wonderful, (6)
"Furnished just right. A/C could work a little better and slight sewer smell in bath"
United States
Eddie G.
BestStays@Queen Bee Cozy for couples and small families

3-bedroom house with WiFi and AC in Lindale close to downtown and I-20

Lindale
9.8 out of 10, Exceptional, (6)
"The home was very clean and well decorated. The host responded to questions very quick. This property is about 13 miles from Tyler, 27 miles from Canton. "
United States
DAVID M.
The price is AU$247
includes taxes & fees
14 Dec - 15 Dec
3-bedroom house with WiFi and AC in Lindale close to downtown and I-20

STAY TYLER @Alamo Lux Livin up to 11-Fast wifi

Tyler
10.0 out of 10, Exceptional, (78)
"Awesome place, we loved it! "
United States
Steven C.
The price is AU$480
includes taxes & fees
9 Dec - 10 Dec
STAY TYLER @Alamo Lux Livin up to 11-Fast wifi

Willow's Cabin - Cozy Cabin Nestled In The Woods

Gilmer
10.0 out of 10, Exceptional, (93)
"This place was perfect for our two night stay in the area. Great communication with the owner and the hot tub was a winner. We’ll definitely stay here in the future!"
United States
Mike S.
Willow's Cabin - Cozy Cabin Nestled In The Woods

Stay Tyler @ Parade of Homes

Tyler
9.8 out of 10, Exceptional, (27)
"Great property. Would stay there again"
United States
Adam H.
The price is AU$566
includes taxes & fees
9 Dec - 10 Dec
Stay Tyler @ Parade of Homes

A 4 bedroom beautiful custom home located 5 miles away from downtown Tyler, Tx.

Flint
9.4 out of 10, Exceptional, (45)
"We really enjoyed our stay here. The house was very spacious and well taken care of. Next time we are visiting family in the area we will be renting here again!"
United States
Jessica I.
A 4 bedroom beautiful custom home located 5 miles away from downtown Tyler, Tx.

City Zen: Modern Country Retreat

Lindale
10.0 out of 10, Exceptional, (15)
"Everything was great and the house is really beautiful and nice and clean"
United States
Yolanda S.
The price is AU$624
includes taxes & fees
9 Dec - 10 Dec
City Zen: Modern Country Retreat

Cozy 2 bedroom 2 bath duplex near UT Tyler!

Tyler
9.6 out of 10, Exceptional, (40)
"Would rent again."
Canada
Joann
The price is AU$310
includes taxes & fees
14 Dec - 15 Dec
Cozy 2 bedroom 2 bath duplex near UT Tyler!

Serenity Place

Tyler
9.6 out of 10, Exceptional, (4)
"Everything was perfect and very comfortable! "
United States
Stephanie A.
Serenity Place

Tyler's Texas Rose, a beautiful 2BR/1BA house with back yard

Tyler
8.4 out of 10, Very good, (15)
"The King Bed was firmer then I would like and the shower worked ok."
United States
David S.
Tyler's Texas Rose, a beautiful 2BR/1BA house with back yard
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

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$175 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?

Relaxing Country Stay with Events Welcome!: This highly rated holiday home rental in Winona offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Winona?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winona stay.

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.