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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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 AED 551
AED 653 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 1,286
AED 1,521 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 915
AED 1,085 total
includes taxes & fees
10 Nov - 11 Nov
Charming ranch style log cabin with AC in scenic Winona
A dining area with round wooden tables and chairs, a television, and potted plants.

4. 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 AED 214
AED 252 total
includes taxes & fees
3 Dec - 4 Dec
Grenada MS | King Bed
A living room with a sectional sofa, armchairs, a coffee table, and a dining area with a table and chairs.

5. 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 AED 657
AED 1,179 total
includes taxes & fees
23 Nov - 24 Nov
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.

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 AED 240
AED 280 total
includes taxes & fees
22 Nov - 23 Nov
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 AED 240
AED 280 total
includes taxes & fees
22 Nov - 23 Nov
King Bed Accessible|Grenada MS
77f49a8d

8. 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)
"Cabin was nice clean and was so easy to check"
United States
Kathy B.
The price is AED 551
AED 1,234 total
includes taxes & fees
12 Nov - 13 Nov
The Crappie-2 bedroom cabin with spacious parking
IMG_1772

9. 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 AED 643
AED 1,104 total
includes taxes & fees
22 Nov - 23 Nov
The most unique getaway experience in North Mississippi!
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10. Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (21 reviews)
"Clean and excellent A/C even during very hot weather. Beds were comfortable. Good choice."
United States
Carol W.
The price is AED 551
AED 998 total
includes taxes & fees
30 Nov - 1 Dec
Dogwoods-2 bedroom cabin with spacious parking
A living room with two black leather sofas, a patterned rug, and a dark wooden cabinet.

11. 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)
"The location was great and the size and space were fantastic. I will book this house again."
United States
JACQUELINE T.
The price is AED 545
AED 1,220 total
includes taxes & fees
10 Nov - 11 Nov
Magnolia State Winter Escape – Beautiful 3BR Family Home
A covered porch with a cushioned bench and decorative pillows, a wooden railing, and a clear view of the surrounding landscape.

12. 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)
"Great little cabin for a getaway. Quiet and secluded."
United States
Mark H.
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Exterior

13. Grenada Lake Resort Cabin # 5

Grenada Lake Resort Cabin # 5
Coffeeville
9.8 out of 10, Exceptional, (7 reviews)
"we loved staying her. it was a perfect place to stay. cozy, comfortable, and clean. "
United States
Kevin
The price is AED 353
AED 542 total
includes taxes & fees
10 Nov - 11 Nov
Grenada Lake Resort Cabin # 5
A wooden deck with a view of a lake, a grill, and a grill cover.

14. The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake
Grenada
9.8 out of 10, Exceptional, (21 reviews)
"Great property to stay at if you are staying or fishing in the Grenada area. "
United States
Jay R.
The price is AED 735
AED 1,269 total
includes taxes & fees
22 Nov - 23 Nov
The Get-A-Way at Grenada lake
Exterior

15. Grenada Lake Resort Cabin # 4

Grenada Lake Resort Cabin # 4
Coffeeville
9.6 out of 10, Exceptional, (5 reviews)
"Smooth booking process. Booked within two days of our visit. Very clean. Pricing was very reasonable. The host was very communicative when I had questions before booking and had responded pretty fast. Will absolutely be saving this location for future visits."
United States
Sharon C.
The price is AED 353
AED 542 total
includes taxes & fees
10 Nov - 11 Nov
Grenada Lake Resort Cabin # 4
A cozy cabin interior with a living room, a staircase, and a kitchen area.

16. Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.
Coffeeville
10.0 out of 10, Exceptional, (47 reviews)
"Great cabin with lots of room for families!"
United States
Scotty H.
The price is AED 735
AED 1,281 total
includes taxes & fees
16 Nov - 17 Nov
Cabin in the woods overlooking Grenada lake.
A living room with a fireplace, a television, and a sofa.

17. 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 AED 496
AED 1,100 total
includes taxes & fees
16 Nov - 17 Nov
Charming family retreat
Private kitchen

18. 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 AED 1,388
AED 2,116 total
includes taxes & fees
12 Nov - 13 Nov
House Located Less Than 3 Miles of Grenada Lake
A dining area with round wooden tables and chairs, a television, and potted plants.

19. 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 AED 240
AED 282 total
includes taxes & fees
3 Dec - 4 Dec
2 Queen Bed|Smk|Grenada MS
A dining area with round wooden tables and chairs, a television, and potted plants.

20. 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 AED 265
AED 310 total
includes taxes & fees
22 Nov - 23 Nov
Grenada MS |2 Queen Bed
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

Holiday Inn Express & Suites Grenada by IHG

Holiday Inn Express & Suites Grenada by IHG

10/10 Excellent
"Nous avons beaucoup apprécié l’accueil de Judith. Elle nous a fourni tout ce qui nous manquait. Cette femme est très chaleureuse et sympathique. Par contre il y avait des clients très dérangeant qui s’engeulaient dans le passage près de notre chambre. Le bain et la toilette n’était pas propre du tout."
Lucie 1-night trip
Posted 9 days ago
Holiday Inn Express & Suites Grenada by IHG

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.