Winona Vacation Rentals

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Vacation 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.
$151 nightly
The price is $159
Nov 24 - Nov 25
Total with taxes and fees
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, (26)
"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."
United States
Caitlin M.
$139 nightly
The price is $146
Dec 1 - Dec 2
Total with taxes and fees
Charming and Historic Holly Cottage Carriage House in Downtown Tyler

Cora's Cabins

3.0 star property
Tyler
9.4 out of 10, Exceptional, (154)
"Enjoyed the stay "
United States
Benito
$145 nightly
The price is $152
Dec 24 - Dec 25
Total with taxes and fees
Cora's Cabins

Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Tyler
10.0 out of 10, Exceptional, (30)
"Our family had a great time staying here! The kids LOVED the loft, the sheep, & the livestock guardian dog Roxy! "
United States
Kayla B.
$101 nightly
The price is $106
Nov 25 - Nov 26
Total with taxes and fees
Guesthouse on peaceful 11+ acre homestead! Pet friendly!

Cana Cottage | Farm Stay

Tyler
10.0 out of 10, Exceptional, (41)
"Good design, well maintained "
United States
William
$109 nightly
The price is $114
Dec 4 - Dec 5
Total with taxes and fees
Cana Cottage | Farm Stay

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

Hawkins
10.0 out of 10, Exceptional, (247)
"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 @ 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
$296 nightly
The price is $311
Nov 24 - Nov 25
Total with taxes and fees
STAY TYLER @ Vine- near shops- Fast Wifi

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

Hawkins
10.0 out of 10, Exceptional, (237)
"The home was wonderful. "
United States
Jonnie C.
Vintage Cottage on Lake!<br>Fish Camp Cabin<br>FREE kayak, canoe & bike use!<br>

BestStays@Queen Bee Cozy for couples and small families

Tyler
8.8 out of 10, Excellent, (5)
"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

STAY TYLER @ Faulkner- amazing location

Tyler
10.0 out of 10, Exceptional, (30)
"Had a great stay."
United States
Edward M.
$335 nightly
The price is $353
Nov 30 - Dec 1
Total with taxes and fees
STAY TYLER @ Faulkner- amazing location

Cozy 2 bedroom 2 bath duplex near UT Tyler!

Tyler
9.6 out of 10, Exceptional, (39)
"Would rent again."
Canada
Joann
$188 nightly
The price is $198
Nov 24 - Nov 25
Total with taxes and fees
Cozy 2 bedroom 2 bath duplex near UT Tyler!

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

Longview
10.0 out of 10, Exceptional, (37)
"Comfortable and relaxing place to stay. "
United States
Nicholas T.
THE FAIRWAY: Modern 3BR with beautiful golf course views and convenient location

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

Tyler
10.0 out of 10, Exceptional, (77)
"Awesome place, we loved it! "
United States
Steven C.
$324 nightly
The price is $341
Nov 30 - Dec 1
Total with taxes and fees
STAY TYLER @Alamo Lux Livin up to 11-Fast wifi

Cozy cabin in charming Hawkins with AC

Hawkins
9.0 out of 10, Wonderful, (7)
"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. "
United States
Benny G.
$115 nightly
The price is $127
Dec 1 - Dec 2
Total with taxes and fees
Cozy cabin in charming Hawkins with AC

Cabin with Pond, Trails, and Farm Experience

Flint
9.8 out of 10, Exceptional, (67)
"Our third stay here. Our daughters love it and ask to go back over and over "
United States
Michael D.
$313 nightly
The price is $329
Dec 15 - Dec 16
Total with taxes and fees
Cabin with Pond, Trails, and Farm Experience

Beautiful Azalea District 2 Masters

Tyler
9.8 out of 10, Exceptional, (18)
"Beautiful and spacious home in a wonderful and quiet neighborhood! Loved our stay!"
United States
Gillian S.
Beautiful Azalea District 2 Masters

Stay Tyler @ Parade of Homes

Tyler
9.8 out of 10, Exceptional, (27)
"Great property. Would stay there again"
United States
Adam H.
$358 nightly
The price is $377
Dec 2 - Dec 3
Total with taxes and fees
Stay Tyler @ Parade of Homes

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.
$154 nightly
The price is $162
Dec 14 - Dec 15
Total with taxes and fees
3-bedroom house with WiFi and AC in Lindale close to downtown and I-20

The Carriage House, The Carriage House at Jeter Farmhouse

Gladewater
9.6 out of 10, Exceptional, (7)
"Very nice rental "
United States
michael S.
$129 nightly
The price is $135
Nov 26 - Nov 27
Total with taxes and fees
The Carriage House, The Carriage House at Jeter Farmhouse

Grable Creek Farmhouse

Longview
9.8 out of 10, Exceptional, (39)
"Very nice stay, ac is great, easy access, exactly as represented, very helpful information, comfortable accommodations."
United States
James R.
Grable Creek Farmhouse
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 $106 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?

Relaxing Country Stay with Events Welcome!: This Winona vacation home rental offers a garden, a selection of games, and a barbecue grill 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 Santa Land, 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.