Winona Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Winona

Our top choices for Winona vacation rentals

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

Charming ranch style log cabin with AC in scenic 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!"
The price is ￥36,755
￥45,533 total
includes taxes & fees
Oct 22 - Oct 23
Charming ranch style log cabin with AC in scenic Winona
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Property grounds

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

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. "
The price is ￥22,142
￥27,514 total
includes taxes & fees
Oct 22 - Oct 23
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Charming 3-bedroom barn in quaint Winona with AC
Interior

Charming 3-bedroom barn in quaint Winona with AC

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."
The price is ￥51,664
￥64,358 total
includes taxes & fees
Oct 2 - Oct 3
Charming 3-bedroom barn in quaint Winona with AC
The most unique getaway experience in North Mississippi!
Exterior

The most unique getaway experience in North Mississippi!

10.0 out of 10, Exceptional, (3)
"Had a very nice time. Nice place to just get away and enjoy some peace"
The price is ￥25,832
￥44,239 total
includes taxes & fees
Sep 28 - Sep 29
The most unique getaway experience in North Mississippi!
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Fridge, microwave, oven, stovetop

4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

10.0 out of 10, Exceptional, (2)
"Amazing home and outdoor patio with pool! This place is beautiful and very close to Grenada Lake boat launch. "
The price is ￥73,805
￥133,620 total
includes taxes & fees
Oct 8 - Oct 9
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Exterior

Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown

2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very nice stay, it’s the nicest house in the area! A lot of parking! "
Massive Grenada Brick Home: Perfect for Summer Getaway Close to Downtown
Cabin in the woods overlooking Grenada lake.
Dining

Cabin in the woods overlooking Grenada lake.

10.0 out of 10, Exceptional, (36)
"We enjoyed our stay!"
The price is ￥29,522
￥54,174 total
includes taxes & fees
Oct 8 - Oct 9
Cabin in the woods overlooking Grenada lake.
The Crappie-2 bedroom cabin with spacious parking
Exterior

The Crappie-2 bedroom cabin with spacious parking

10.0 out of 10, Exceptional, (5)
"This was the perfect private family-friendly spot, especially traveling from Texas to visit family when you're not familiar with the area. The host was responsive and considerate, ensuring our stay was comfortable from start to finish."
The price is ￥22,142
￥48,989 total
includes taxes & fees
Oct 8 - Oct 9
The Crappie-2 bedroom cabin with spacious parking
Greenwood Studio Cottage < 1 Mi to Downtown!
Apartment (0 Bedroom) | Interior

Greenwood Studio Cottage < 1 Mi to Downtown!

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,"
Greenwood Studio Cottage < 1 Mi to Downtown!
Bream Shack-2 bedroom cabin with spacious parking
Interior

Bream Shack-2 bedroom cabin with spacious parking

8.4 out of 10, Very Good, (5)
"Impeccable!"
The price is ￥20,665
￥47,093 total
includes taxes & fees
Oct 5 - Oct 6
Bream Shack-2 bedroom cabin with spacious parking
Dogwoods-2 bedroom cabin with spacious parking
Fridge, microwave, oven, stovetop

Dogwoods-2 bedroom cabin with spacious parking

9.6 out of 10, Exceptional, (14)
"Quick overnight stay for fishing trip everything was great, The only complaint was it seemed there something on the sheets in queen bed."
The price is ￥22,142
￥39,343 total
includes taxes & fees
Sep 28 - Sep 29
Dogwoods-2 bedroom cabin with spacious parking
The Get-A-Way at Grenada lake
Fridge, microwave, oven, stovetop

The Get-A-Way at Grenada lake

9.8 out of 10, Exceptional, (12)
"Great place to stay for a fishing getaway ,close to the lake and not far from town . Owner was very responsive to my text , love that you can back your boats up under the shelter will definitely stay here again if we come down again!"
The price is ￥29,522
￥54,016 total
includes taxes & fees
Sep 25 - Sep 26
The Get-A-Way at Grenada lake
Charming family retreat
Outdoor dining

Charming family retreat

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 "
The price is ￥23,249
￥50,306 total
includes taxes & fees
Sep 28 - Sep 29
Charming family retreat
Homey Greenwood Getaway w/ Patio & Backyard
House (2 Bedrooms) | Interior

Homey Greenwood Getaway w/ Patio & Backyard

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard
Located 3 miles to Grenada Lake
Fridge, microwave, oven, stovetop

Located 3 miles to Grenada Lake

10.0 out of 10, Exceptional, (1)
"Very Peaceful and relaxing "
Located 3 miles to Grenada Lake
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Dining

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

10.0 out of 10, Exceptional, (11)
"Nice quiet and clean location to share with family and friends"
The price is ￥26,422
￥49,120 total
includes taxes & fees
Oct 8 - Oct 9
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Fridge, microwave, oven, stovetop

5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

10.0 out of 10, Exceptional, (7)
"Our stay was shorter than what we expected, but everything was just perfect"
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Terrace/patio

2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

10.0 out of 10, Exceptional, (1)
"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!"
The price is ￥22,142
￥36,801 total
includes taxes & fees
Oct 1 - Oct 2
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!
Apartment (2 Bedrooms) | Interior

Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

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!!"
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!
The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district
Fridge, microwave, oven, stovetop

The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district

9.8 out of 10, Exceptional, (7)
"Beautifully decorated, spacious, quiet getaway from the bustling metropolis I call home. Owner was friendly and responsive! "
The Postmaster's Quarters at 2nd & Main - 2 story apartment in the historic district
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

Americas Best Value Inn Winona

Americas Best Value Inn Winona

10/10 Excellent
"Excellent service thank you."
Violet 3-night trip
Posted 2 days ago
Americas Best Value Inn Winona

Find out more about Winona

Find out more about Winona

Search for holiday rentals in Winona on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winona!

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 has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Winona - Montgomery County Library, and Middleton Cemetery. 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.