Holiday Rentals in Winona

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Holiday Rentals in Winona

Relaxing Country Stay with Events Welcome!
9.8 out of 10, Exceptional, (19)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
The price is €141
includes taxes & fees
19 Oct - 20 Oct
Relaxing Country Stay with Events Welcome!
Cana Cottage | Farm Stay
10.0 out of 10, Exceptional, (36)
"Perfect for my daughter’s wedding night. Super close to the venue. "
The price is €108
includes taxes & fees
16 Oct - 17 Oct
Cana Cottage | Farm Stay
Charming and Historic Holly Cottage Carriage House in Downtown Tyler
2.0 star property
9.8 out of 10, Exceptional, (25)
"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 €130
includes taxes & fees
19 Oct - 20 Oct
Charming and Historic Holly Cottage Carriage House in Downtown Tyler
Cora's Cabins
3.0 star property
9.4 out of 10, Exceptional, (153)
"Enjoyed the stay "
The price is €135
includes taxes & fees
2 Nov - 3 Nov
Cora's Cabins
Guesthouse on peaceful 11+ acre homestead! Pet friendly!
10.0 out of 10, Exceptional, (27)
"It felt like home."
The price is €106
includes taxes & fees
22 Oct - 23 Oct
Guesthouse on peaceful 11+ acre homestead! Pet friendly!
Cozy vineyard studio with peaceful pond views.
10.0 out of 10, Exceptional, (2)
"It is an excellent place to stay. Very clean, comfortable, and quiet. Great host. Look forward to staying there again. "
The price is €172
includes taxes & fees
19 Oct - 20 Oct
Cozy vineyard studio with peaceful pond views.
Cozy cabin in charming Hawkins with AC
8.4 out of 10, Very good, (5)
"Thelma did a great job of taking care of us. The hot tub was amazing. A good place to get away from the everything. Pet friendly. "
The price is €108
includes taxes & fees
26 Oct - 27 Oct
Cozy cabin in charming Hawkins with AC
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 Carriage House, The Carriage House at Jeter Farmhouse
The Cottage at Dogwood Ridge.
10.0 out of 10, Exceptional, (107)
"Comfortable, clean, good location, friendly hosts! "
The price is €149
includes taxes & fees
20 Oct - 21 Oct
The Cottage at Dogwood Ridge.
Cozy Wood Cottage in Tyler
2.0 star property
Cozy Wood Cottage in Tyler
Hot Tub, Projector, King Bed, Yard Games, Family Fun & Vintage Retreat
10.0 out of 10, Exceptional, (5)
"Great decor, shower, nostalgic...projector system was a nice addition, thoughtful items for children: books, toys, drawing material etc"
The price is €316
includes taxes & fees
19 Oct - 20 Oct
Hot Tub, Projector, King Bed, Yard Games, Family Fun & Vintage Retreat
Spacious 1-Bedroom Guesthouse in the Woods
10.0 out of 10, Exceptional, (44)
"Awesome place will stay again, would"
The price is €120
includes taxes & fees
19 Oct - 20 Oct
Spacious 1-Bedroom Guesthouse in the Woods
"Torquoise" Hospitals district/TJC smart TV’s in all bedrooms
2.0 star property
The price is €197
includes taxes & fees
19 Oct - 20 Oct
"Torquoise" Hospitals district/TJC smart TV’s in all bedrooms
Glamorous Pink Rose of Tyler!
2.0 star property
10.0 out of 10, Exceptional, (8)
"Super easy and great spot"
The price is €273
includes taxes & fees
19 Oct - 20 Oct
Glamorous Pink Rose of Tyler!
Historic House, modern amenities and large front porch, short walk downtown
2.0 star property
8.8 out of 10, Excellent, (5)
"The house was lovely and offered historic charm as well as modern comforts. It is walking distance to shops and restaurants. The hosts were attentive and gave clear and easy instructions. Note that the house is close to the railroad tracks and the occasional train can be heard, including in the middle of the night. "
The price is €140
includes taxes & fees
26 Oct - 27 Oct
Historic House, modern amenities and large front porch, short walk downtown
Charming Home in the Piney Woods of East Texas
9.4 out of 10, Exceptional, (17)
"Very clean easy check in overall Very happy with my stay"
Charming Home in the Piney Woods of East Texas
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 €296
includes taxes & fees
20 Oct - 21 Oct
Casa del Lago at Sandy Point ~ Charming 3 bedroom house with amazing lake views
Cozy Tiny Home in Heart of Big Sandy
9.4 out of 10, Exceptional, (23)
"Very nuce perfect size for just the husband and I. Could have used just a little more privacy in the front sitting area oitside. But overall, great experience. "
The price is €127
includes taxes & fees
16 Oct - 17 Oct
Cozy Tiny Home in Heart of Big Sandy
Treehouse at Berry-patch
8.4 out of 10, Very good, (6)
"Bed was super comfy, shower was amazing, and the only thing that was missing was nice weather so we could sit on the porch in the morning. Very clean, really nicely decorated, felt like home. "
The price is €190
includes taxes & fees
15 Nov - 16 Nov
Treehouse at Berry-patch
Charming 3-bedroom house on quiet street in delightful Kilgore
9.4 out of 10, Exceptional, (3)
"Clean home, excellent host"
Charming 3-bedroom house on quiet street in delightful 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

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, apart-hotels, 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 favorite 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 depends 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 €108 per night. Entering your travel dates in the search wizard you might find 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?

A 1921 Craftsman with Charm in Tyler!: This holiday home rental outside of Winona has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.