A brick building with the inscription "WINONA" and an arched window.

Winona Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winona vacation rentals

A wooden cabin with a balcony, surrounded by trees.

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

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Winona
10.0 out of 10, Exceptional, (1 review)
"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.
The price is ￥23,678
￥29,422 total
includes taxes & fees
Oct 17 - Oct 18
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
A wooden door with two glass panels, a wreath on each, and a sign reading "1418B".

2. Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC
Winona
8.0 out of 10, Very good, (2 reviews)
"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.
The price is ￥55,248
￥68,823 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3-bedroom barn in quaint Winona with AC
A cozy cabin interior with a wooden ceiling, a ceiling fan, a kitchen area with a refrigerator and stove, a dining area with a table and chairs, and a living room with a couch.

3. Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona
Winona
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean, comfortable cabin with everything you need. "
United States
Lee T.
The price is ￥39,305
￥49,036 total
includes taxes & fees
Oct 4 - Oct 5
Charming ranch style log cabin with AC in scenic Winona
A living room with a sectional sofa, armchairs, a coffee table, and a dining area with a table and chairs.

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

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Grenada
9.6 out of 10, Exceptional, (16 reviews)
"The property was easy to find, very clean, and the beds were very comfortable. Great place to stay and cozy."
United States
Joahua
The price is ￥21,191
￥44,463 total
includes taxes & fees
Oct 4 - Oct 5
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
A dining area with round wooden tables and chairs, a television, and potted plants.

5. Grenada MS | King Bed

Grenada MS | King Bed
Grenada MS
10.0 out of 10, Exceptional, (57 reviews)
"Stopped here for one night and it comfortably met all expectations."
United States
Anonymous traveler
The price is ￥13,394
￥15,453 total
includes taxes & fees
Oct 25 - Oct 26
Grenada MS | King Bed
A dining area with round wooden tables and chairs, a television, and potted plants.

6. Grenada MS | King Bed Smoking

Grenada MS | King Bed Smoking
Grenada MS
10.0 out of 10, Exceptional, (48 reviews)
"Rooms had ample space for two guests, creating a very inviting atmosphere."
United States
Anonymous traveler
The price is ￥13,394
￥15,453 total
includes taxes & fees
Oct 25 - Oct 26
Grenada MS | King Bed Smoking
A spacious living room with a large flat-screen TV, comfortable seating, and a Christmas tree.

7. King Bed Accessible|Grenada MS

King Bed Accessible|Grenada MS
Grenada MS
10.0 out of 10, Exceptional, (67 reviews)
"Saw several families staying here,lots of space seemed great for everyone involved."
United States
Anonymous traveler
The price is ￥13,394
￥15,453 total
includes taxes & fees
Oct 28 - Oct 29
King Bed Accessible|Grenada MS
fe118567

8. Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (20 reviews)
"Cabin was very clean and comfortable. We’ll be staying there again for sure."
United States
Gabe S.
The price is ￥23,678
￥44,928 total
includes taxes & fees
Oct 4 - Oct 5
Dogwoods-2 bedroom cabin with spacious parking
77f49a8d

9. The Crappie-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking
Grenada
10.0 out of 10, Exceptional, (7 reviews)
"The Crappie cabin was exactly as it was listed. Very clean great place to stay highly recommended this place great communication from host "
United States
Kevin D.
The price is ￥23,678
￥55,750 total
includes taxes & fees
Oct 4 - Oct 5
The Crappie-2 bedroom cabin with spacious parking
A living room with two black leather sofas, a patterned rug, and a dark wooden cabinet.

10. Magnolia State Winter Escape – Beautiful 3BR Family Home

Magnolia State Winter Escape – Beautiful 3BR Family Home
Grenada
9.0 out of 10, Wonderful, (11 reviews)
"Great atmosphere and great area near downtown Grenada..."
United States
Lelabug G.
The price is ￥23,441
￥54,978 total
includes taxes & fees
Oct 4 - Oct 5
Magnolia State Winter Escape – Beautiful 3BR Family Home
IMG_1772

11. The most unique getaway experience in North Mississippi!

The most unique getaway experience in North Mississippi!
Grenada
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property and view great host clean places loved it so much "
United States
Austin R.
The price is ￥27,624
￥49,657 total
includes taxes & fees
Oct 11 - Oct 12
The most unique getaway experience in North Mississippi!
Exterior

12. Grenada Lake Resort Cabin # 2

Grenada Lake Resort Cabin # 2
Coffeeville
10.0 out of 10, Exceptional, (2 reviews)
"Nice quite area cozy and rustic interior of the cabin "
United States
James
The price is ￥15,154
￥24,660 total
includes taxes & fees
Oct 4 - Oct 5
Grenada Lake Resort Cabin # 2
Exterior

13. Grenada Lake Resort Cabin # 1

Grenada Lake Resort Cabin # 1
Coffeeville
10.0 out of 10, Exceptional, (3 reviews)
"Great for peace and quiet"
United States
Summer
The price is ￥15,154
￥24,660 total
includes taxes & fees
Oct 6 - Oct 7
Grenada Lake Resort Cabin # 1
A covered porch with a cushioned bench and decorative pillows, a wooden railing, and a clear view of the surrounding landscape.

14. Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters

Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Greenwood
10.0 out of 10, Exceptional, (5 reviews)
"Amazing cabin, in a great location with a great host"
United States
Conner M.
The price is ￥18,468
￥23,139 total
includes taxes & fees
Oct 12 - Oct 13
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
A wooden deck with a view of a lake, a grill, and a grill cover.

15. The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake
Grenada
9.8 out of 10, Exceptional, (18 reviews)
"Great property to stay at if you are staying or fishing in the Grenada area. "
United States
Jay R.
The price is ￥31,570
￥57,257 total
includes taxes & fees
Oct 12 - Oct 13
The Get-A-Way at Grenada lake
A living room with a fireplace, a television, and a sofa.

16. Charming family retreat

Charming family retreat
Greenwood
9.2 out of 10, Wonderful, (5 reviews)
"Neat little town. Enjoy our stay"
United States
Robert W.
The price is ￥24,861
￥53,795 total
includes taxes & fees
Oct 7 - Oct 8
Charming family retreat
Private kitchen

17. House Located Less Than 3 Miles of Grenada Lake

House Located Less Than 3 Miles of Grenada Lake
Coffeeville
8.6 out of 10, Excellent, (4 reviews)
"Everything was wonderful!!"
United States
anna a.
The price is ￥59,667
￥96,012 total
includes taxes & fees
Oct 6 - Oct 7
House Located Less Than 3 Miles of Grenada Lake
A dining area with round wooden tables and chairs, a television, and potted plants.

18. 2 Queen Bed|Smk|Grenada MS

2 Queen Bed|Smk|Grenada MS
Grenada MS
10.0 out of 10, Exceptional, (52 reviews)
"Cozy beds and welcoming staff made our visit enjoyable. Free WiFi was an extra perk too."
United States
Anonymous traveler
The price is ￥14,733
￥16,996 total
includes taxes & fees
Oct 25 - Oct 26
2 Queen Bed|Smk|Grenada MS
A dining area with round wooden tables and chairs, a television, and potted plants.

19. Grenada MS |2 Queen Bed

Grenada MS |2 Queen Bed
Grenada MS
10.0 out of 10, Exceptional, (66 reviews)
"Quiet location made it easy to relax after busy days exploring Jackson."
United States
Anonymous traveler
The price is ￥14,733
￥16,996 total
includes taxes & fees
Oct 25 - Oct 26
Grenada MS |2 Queen Bed
IMG_1772

20. The most unique getaway experience in North Mississippi!

The most unique getaway experience in North Mississippi!
Grenada
The price is ￥27,624
￥61,323 total
includes taxes & fees
Oct 6 - Oct 7
The most unique getaway experience in North Mississippi!
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

Baymont by Wyndham Grenada

Baymont by Wyndham Grenada

8/10 Good
"Clean room, hot water and Fox News. Not enough pillows and the breakfast food was just gross."
Sheri 1-night trip
Posted 18 hours ago
Baymont by Wyndham Grenada

Find out more about Winona

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Frequently asked questions

Are there vacation rentals in Winona?

Yes, there are vacation rentals in Winona close to Montgomery County Performing Arts Center, or you can select a more secluded option if you're looking for a relaxing 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 offers a balcony, a selection of games, and air-conditioning 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, Middleton Cemetery, and Winona Country Club. Winona - Montgomery County Library and Winona City Hall 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.