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

Winona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winona vacation rentals

Exterior

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 689 total
includes taxes & fees
9 Aug - 10 Aug
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Exterior detail

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 1,601 total
includes taxes & fees
9 Aug - 10 Aug
Charming 3-bedroom barn in quaint Winona with AC
Smart TV

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 1,141 total
includes taxes & fees
9 Aug - 10 Aug
Charming ranch style log cabin with AC in scenic Winona
Exterior

4. 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 574 total
includes taxes & fees
10 Aug - 11 Aug
Grenada Lake Resort Cabin # 5
Exterior

5. 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 AED 353
AED 574 total
includes taxes & fees
9 Aug - 10 Aug
Grenada Lake Resort Cabin # 1
Terrace/patio

6. Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (18 reviews)
"Cabin was very clean and comfortable. We’ll be staying there again for sure."
United States
Gabe S.
The price is AED 551
AED 1,045 total
includes taxes & fees
10 Aug - 11 Aug
Dogwoods-2 bedroom cabin with spacious parking
Exterior detail

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 341
AED 393 total
includes taxes & fees
8 Sep - 9 Sep
King Bed Accessible|Grenada MS
Dining

8. 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 341
AED 393 total
includes taxes & fees
8 Sep - 9 Sep
Grenada MS | King Bed
Dining

9. 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 341
AED 393 total
includes taxes & fees
8 Sep - 9 Sep
Grenada MS | King Bed Smoking
TV

10. 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 AED 551
AED 1,297 total
includes taxes & fees
9 Aug - 10 Aug
The Crappie-2 bedroom cabin with spacious parking
Interior

11. Minutes away from one of the greatest crappie fishing lakes in the world

Minutes away from one of the greatest crappie fishing lakes in the world
Coffeeville
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay and great host! "
United States
Josh P.
The price is AED 735
AED 888 total
includes taxes & fees
10 Aug - 11 Aug
Minutes away from one of the greatest crappie fishing lakes in the world
Property grounds

12. 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 1,171 total
includes taxes & fees
10 Aug - 11 Aug
The most unique getaway experience in North Mississippi!
Smart TV

13. Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.
Coffeeville
10.0 out of 10, Exceptional, (44 reviews)
"It was amazing and we will be coming back!"
United States
Elisha B.
The price is AED 735
AED 1,348 total
includes taxes & fees
9 Aug - 10 Aug
Cabin in the woods overlooking Grenada lake.
Property grounds

14. 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 AED 735
AED 1,332 total
includes taxes & fees
9 Aug - 10 Aug
The Get-A-Way at Grenada lake
Smart TV, fireplace, DVD player, books

15. 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
10.0 out of 10, Exceptional, (14 reviews)
"Nice quiet and clean location to share with family and friends"
United States
Janet T.
The price is AED 657
AED 1,234 total
includes taxes & fees
17 Aug - 18 Aug
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Terrace/patio

16. 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, (4 reviews)
"Great little cabin for a getaway. Quiet and secluded."
United States
Mark H.
The price is AED 397
AED 503 total
includes taxes & fees
9 Aug - 10 Aug
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters
Smart TV

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

Magnolia State Winter Escape – Beautiful 3BR Family Home
Grenada
9.0 out of 10, Wonderful, (10 reviews)
"Great atmosphere and great area near downtown Grenada..."
United States
Lelabug G.
The price is AED 562
AED 1,301 total
includes taxes & fees
9 Aug - 10 Aug
Magnolia State Winter Escape – Beautiful 3BR Family Home
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 2,234 total
includes taxes & fees
9 Aug - 10 Aug
House Located Less Than 3 Miles of Grenada Lake
Smart TV

19. Charming family retreat

Charming family retreat
Greenwood
9.6 out of 10, Exceptional, (4 reviews)
"Neat little town. Enjoy our stay"
United States
Robert W.
The price is AED 579
AED 1,252 total
includes taxes & fees
9 Aug - 10 Aug
Charming family retreat
Exterior

20. 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 AED 353
AED 574 total
includes taxes & fees
9 Aug - 10 Aug
Grenada Lake Resort Cabin # 2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Hampton Inn & Suites Grenada

Hampton Inn & Suites Grenada

10/10 Excellent
"Very clean"
Kimberlie 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Grenada

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, Winona City Hall, and Middleton Cemetery. Winona Country Club and Winona - Montgomery County Library 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.