Winona Vacation Rentals

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Vacation Rentals in Winona

Private kitchen
Charming ranch style log cabin with AC in scenic Winona

Cabin in Winona

10.0 out of 10, Exceptional, (1)
"First time staying in a cabin and was absolutely impressed! It was such a peaceful stay especially coming from being in the daily city life! David was awesome at communicating. Will be reserving again for sure!"
United States
Cierra O.
$285 nightly
The price is $311
Nov 21 - Nov 22
Total with taxes and fees
Charming ranch style log cabin with AC in scenic Winona
Property grounds
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Cabin in Winona

10.0 out of 10, Exceptional, (1)
"This is a cute little rustic cabin. Chad was very friendly and open to suggestions due to being a first time host. "
United States
Trey H.
$171 nightly
The price is $186
Nov 21 - Nov 22
Total with taxes and fees
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Interior
Charming 3-bedroom barn in quaint Winona with AC

Vacation Home in Winona

6.0 out of 10, (1)
"I had a hard time find this place, there need to be sign on old mountain road tell u how to get there. I had to clean one of the bathroom the shower was not clean. There are French door when u enter this place. There need to be some blind to the door."
United States
sherrida r.
$400 nightly
The price is $436
Nov 23 - Nov 24
Total with taxes and fees
Charming 3-bedroom barn in quaint Winona with AC
Exterior
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

Vacation Home in Grenada

2.0 star property
9.4 out of 10, Exceptional, (6)
"Love the house"
United States
Gilbert P.
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Apartment (0 Bedroom) | Interior
Greenwood Studio Cottage < 1 Mi to Downtown!

Apartment in Greenwood

3.5 star property
6.8 out of 10, (3)
"Every thing was great except the bed mattress was very uncomfortable, and the door to the bathroom was sticking when you open and closed it. Overall iitwas an excellent stay,"
United States
Donald
Greenwood Studio Cottage < 1 Mi to Downtown!
Fridge, microwave, oven, stovetop
The Get-A-Way at Grenada lake

Cottage in Grenada

9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay at. The getaway Place was fully stocked and exceptionally clean, we expect to visit again in the fall and will definitely book this place again. ! Host is great, responded to questions almost immediately."
United States
David S.
$341 nightly
The price is $365
Nov 21 - Nov 22
Total with taxes and fees
The Get-A-Way at Grenada lake
Fridge, microwave, oven, stovetop
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

Vacation Home in Grenada

9.2 out of 10, Wonderful, (49)
"My family has stayed here several times, and we enjoy ourselves everytime. Communication with owners was excellent, before, during and after our trips. Great people!"
United States
Girma A.
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.
Outdoor dining
Charming family retreat

Vacation Home in Greenwood

10.0 out of 10, Exceptional, (1)
"If u really wanted stay in the heart of greenwood it’s the perfect place to stay every thing about this house is perfect "
United States
Jamaal C.
$319 nightly
The price is $341
Nov 21 - Nov 22
Total with taxes and fees
Charming family retreat
Apartment (2 Bedrooms) | Interior
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

Apartment in Greenwood

3.0 star property
10.0 out of 10, Exceptional, (2)
"We can't say enough positive about the property and especially the manager/owner. The property is an updated apartment for sure. Clean, well equipped, and spacious. She texted us twice in our four night stay to make sure everything was going well. We highly recommend this property!!! Thank you!!"
United States
Marlynn
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!
House (2 Bedrooms) | Interior
Homey Greenwood Getaway w/ Patio & Backyard

Cottage in Greenwood

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard
Apartment (0 Bedroom) | Interior
Modern Greenwood Studio < 1 Mi to Downtown!

Apartment in Greenwood

3.0 star property
Modern Greenwood Studio < 1 Mi to Downtown!
Fridge, microwave, oven, stovetop
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

Cabin in Grenada

10.0 out of 10, Exceptional, (8)
"We came to Grenada to visit my wife's family. This was the perfect location and cabin for us. It's outside the city and a very peaceful setting. The barn was way more room than we needed. We enjoyed everything about it. "
United States
Brian M.
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Terrace/patio
Minutes away from one of the greatest crappie fishing lakes in the world

Cabin in Coffeeville

10.0 out of 10, Exceptional, (8)
"Beautiful place! Very clean and is equipped with everything you need. The hosts had great communication throughout our stay. Would highly recommend and will definitely be staying again in the future! "
United States
Shayna
$228 nightly
The price is $244
Nov 22 - Nov 23
Total with taxes and fees
Minutes away from one of the greatest crappie fishing lakes in the world
Fridge, microwave, oven, stovetop
The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district

Apartment in Grenada

9.8 out of 10, Exceptional, (7)
"My Husband was training at Camp McCain and I came up to see him for the 4th long weekend. Restaurants in walking distance and the accommodation was nice. Would stay again. "
United States
Rae B.
The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district
Terrace/patio
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

Cabin in Gore Springs

10.0 out of 10, Exceptional, (3)
"THE CABIN WAS AMAZING!! THE VEIWS FROM THE BACK PORCH WAS ABSOLUTELY BREATH TAKING!THE CABIN WAS VERY NICE AND CLEAN. CAN'T WAIT TO GO BACK!"
United States
JANNIE T.
$235 nightly
The price is $251
Nov 21 - Nov 22
Total with taxes and fees
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Dining
Cabin in the woods overlooking Grenada lake.

Vacation Home in Coffeeville

10.0 out of 10, Exceptional, (36)
"Wonderful place and hosts "
United States
Sonya V.
$341 nightly
The price is $365
Nov 21 - Nov 22
Total with taxes and fees
Cabin in the woods overlooking Grenada lake.
Exterior
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.

Vacation Home in French Camp

2.0 star property
8.0 out of 10, Very Good, (1)
"The grounds were just lovely and the fishing was great!"
United States
Maxium R.
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.
Fridge, microwave, oven, stovetop
Located 3 miles to Grenada Lake

Vacation Home in Grenada

10.0 out of 10, Exceptional, (2)
"Very Peaceful and relaxing "
United States
Steve B.
Located 3 miles to Grenada Lake
Dining
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Vacation Home in Grenada

10.0 out of 10, Exceptional, (11)
"Nice quiet and clean location to share with family and friends"
United States
Janet T.
$316 nightly
The price is $338
Dec 21 - Dec 22
Total with taxes and fees
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Property grounds
cabin with WiFi and AC in Gore Springs for hunters/lodging/fishermen

Cabin in Gore Springs

cabin with WiFi and AC in Gore Springs for hunters/lodging/fishermen
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

Hampton Inn & Suites Grenada

Hampton Inn & Suites Grenada

10/10 Excellent
"Room was great. But all drink machines were down, on every floor."
Brentley 1-night trip
Posted 8 days ago
Hampton Inn & Suites Grenada

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 $186 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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winona?

Yes, there are vacation rentals close to popular points of interest in Winona, or you can select a more remote option if you want a relaxing place to stay. Winona is known for its coffeehouses and baseball games. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best vacation home rentals that Winona has to offer?

Charming 3-bedroom barn in quaint Winona with AC: Visitors give good reviews to this Winona vacation home rental, which is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Middleton Cemetery, and Winona - Montgomery County Library. Winona City Hall and Winona Country Club are other places to visit while you're in town.

What are vacation rentals like in Winona?

Vacation rentals are private properties you can stay in for a short or long stay in Winona. Vacation rentals provide amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.