Winona Vacation Rentals

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Our top choices for Winona vacation rentals

Relaxing Country Stay with Events Welcome!

Relaxing Country Stay with Events Welcome!
Winona
10.0 out of 10, Exceptional, (23 reviews)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
United States
Ray T.
$151 nightly
The price is $159
Apr 13 - Apr 14
Total with taxes and fees
Relaxing Country Stay with Events Welcome!

Cana Cottage | Farm Stay

Cana Cottage | Farm Stay
Tyler
10.0 out of 10, Exceptional, (45 reviews)
"The place was lovely. Enjoyed our time with Roxy"
United States
james c.
$117 nightly
The price is $123
Apr 14 - Apr 15
Total with taxes and fees
Cana Cottage | Farm Stay

The Cottage at Dogwood Ridge.

The Cottage at Dogwood Ridge.
Whitehouse
10.0 out of 10, Exceptional, (115 reviews)
"Absolutely loved this place! So peaceful and serene. "
United States
Amy
$170 nightly
The price is $179
Apr 12 - Apr 13
Total with taxes and fees
The Cottage at Dogwood Ridge.

Cozy cabin in charming Hawkins with AC

Cozy cabin in charming Hawkins with AC
Hawkins
9.2 out of 10, Wonderful, (11 reviews)
"Thelma was very welcoming. Even provided delicious cake ball treats."
United States
MARK U.
$110 nightly
The price is $122
May 1 - May 2
Total with taxes and fees
Cozy cabin in charming Hawkins with AC

Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!

Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
Mineola
9.4 out of 10, Exceptional, (31 reviews)
"We attended a wedding just down the road at Hidden Pines. Everything about our stay was excellent!!"
United States
J.B. D.
$157 nightly
The price is $175
Apr 12 - Apr 13
Total with taxes and fees
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!

The Carriage House, The Carriage House at Jeter Farmhouse

The Carriage House, The Carriage House at Jeter Farmhouse
Gladewater
9.8 out of 10, Exceptional, (13 reviews)
"Amazing hosts with beautiful home!"
United States
Emily S.
$129 nightly
The price is $135
Apr 12 - Apr 13
Total with taxes and fees
The Carriage House, The Carriage House at Jeter Farmhouse

Quiet house in the country - 20 minutes from Canton and Lake Fork!

Quiet house in the country - 20 minutes from Canton and Lake Fork!
Mineola
10.0 out of 10, Exceptional, (30 reviews)
"Your property was such a fantastic little place to stay!"
United States
Amy N.
$213 nightly
The price is $238
Apr 12 - Apr 13
Total with taxes and fees
Quiet house in the country - 20 minutes from Canton and Lake Fork!

Chic Suite in Central Longview King Bed

Chic Suite in Central Longview King Bed
Longview
10.0 out of 10, Exceptional, (21 reviews)
"Loved the loft- clean and secure. "
United States
Jessica H.
$256 nightly
The price is $290
Apr 12 - Apr 13
Total with taxes and fees
Chic Suite in Central Longview King Bed

Cozy 2 bedroom 2 bath duplex near UT Tyler!

Cozy 2 bedroom 2 bath duplex near UT Tyler!
Tyler
9.8 out of 10, Exceptional, (47 reviews)
"This house was amazing everything was nice we will definitely be staying again"
United States
Monica M.
$175 nightly
The price is $184
Apr 13 - Apr 14
Total with taxes and fees
Cozy 2 bedroom 2 bath duplex near UT Tyler!

STAY TYLER @ Vine- near shops- Fast Wifi

STAY TYLER @ Vine- near shops- Fast Wifi
Tyler
10.0 out of 10, Exceptional, (65 reviews)
"Clean house, easy access, great location! Fast communication! Would stay here again! "
United States
Jenn E.
$261 nightly
The price is $274
Apr 12 - Apr 13
Total with taxes and fees
STAY TYLER @ Vine- near shops- Fast Wifi

Cozy vineyard studio with peaceful pond views.

Cozy vineyard studio with peaceful pond views.
Gilmer
10.0 out of 10, Exceptional, (6 reviews)
"It is an excellent place to stay. Very clean, comfortable, and quiet. Great host. Look forward to staying there again. "
United States
Joe karen K.
$185 nightly
The price is $195
Apr 19 - Apr 20
Total with taxes and fees
Cozy vineyard studio with peaceful pond views.

Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Charming and Historic Holly Cottage Carriage House in Downtown Tyler
Tyler
9.8 out of 10, Exceptional, (32 reviews)
"Clean comfortable accomodations, beautiful garden and welcoming host!"
United States
Andrea B.
$139 nightly
The price is $146
Apr 12 - Apr 13
Total with taxes and fees
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Guesthouse on peaceful 11+ acre homestead! Pet friendly!
Tyler
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay! It was clean, welcoming, and on a beautiful property!"
United States
Callie C.
$123 nightly
The price is $129
Apr 29 - Apr 30
Total with taxes and fees
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

STAY TYLER @ parklen- 2 mins away from hospitals

STAY TYLER @ parklen- 2 mins away from hospitals
Tyler
10.0 out of 10, Exceptional, (98 reviews)
"The house is very comfortable, and the neighborhood is quiet and well situated. My family and our two dogs very much enjoyed our stay. The hosts were communicative and very helpful. Would stay here again!"
United States
Petula W.
$271 nightly
The price is $285
Apr 12 - Apr 13
Total with taxes and fees
STAY TYLER @ parklen- 2 mins away from hospitals

Historic House, modern amenities and large front porch, short walk downtown

Historic House, modern amenities and large front porch, short walk downtown
Mineola
9.2 out of 10, Wonderful, (7 reviews)
"Great location, very nicely appointed…definitely recommend…"
United States
Harold
$150 nightly
The price is $158
Apr 12 - Apr 13
Total with taxes and fees
Historic House, modern amenities and large front porch, short walk downtown

Home away from Home- Near Tyler Airport

Home away from Home- Near Tyler Airport
Tyler
10.0 out of 10, Exceptional, (3 reviews)
"Very cute place with everything we needed for a peaceful and relaxing stay. The stars and moon were beautiful that night out in the country. "
United States
Jennifer G.
$122 nightly
The price is $128
Apr 16 - Apr 17
Total with taxes and fees
Home away from Home- Near Tyler Airport

Charming 2-bedroom 2 bath duplex in the heart of Tyler!

Charming 2-bedroom 2 bath duplex in the heart of Tyler!
Tyler
10.0 out of 10, Exceptional, (8 reviews)
"Very nice property. I would definitely stay there again."
United States
Craig B.
$188 nightly
The price is $198
Apr 18 - Apr 19
Total with taxes and fees
Charming 2-bedroom 2 bath duplex in the heart of Tyler!

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

STAY TYLER @Alamo Lux Livin up to 11-Fast wifi
Tyler
10.0 out of 10, Exceptional, (81 reviews)
"Clean and cozy. Would definitely stay again."
United States
Mary H.
$292 nightly
The price is $308
Apr 12 - Apr 13
Total with taxes and fees
STAY TYLER @Alamo Lux Livin up to 11-Fast wifi

Just minutes from EVERYTHING! Lots of amenities.

Just minutes from EVERYTHING! Lots of amenities.
Kilgore
9.6 out of 10, Exceptional, (20 reviews)
"Absolutely loved this stay. "
United States
Tricia M.
$215 nightly
The price is $227
Apr 13 - Apr 14
Total with taxes and fees
Just minutes from EVERYTHING! Lots of amenities.

Cozy Tiny Home in Heart of Big Sandy

Cozy Tiny Home in Heart of Big Sandy
Big Sandy
9.4 out of 10, Exceptional, (24 reviews)
"Met some old friends from school, we hung out at the Circle M Crrawfish. We ate, drank, sang karaoke. The tiny home was clean, comfortable. Enjoyed the stay."
United States
Ray W.
$136 nightly
The price is $143
Apr 12 - Apr 13
Total with taxes and fees
Cozy Tiny Home in Heart of Big Sandy
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation 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 vacation.

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 vacation rentals in Winona?

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

What are some of the best vacation home rentals in Winona?

STAY TYLER @ Vine- near shops- Fast Wifi: This vacation home rental near Winona offers a patio, a garden, and air-conditioning 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Winona?

With 3 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Winona like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winona. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.