Winona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winona vacation rentals

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 CA $340
CA $420 total
includes taxes & fees
May 24 - May 25
Charming ranch style log cabin with AC in scenic Winona

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 CA $478
CA $593 total
includes taxes & fees
May 25 - May 26
Charming 3-bedroom barn in quaint Winona with AC

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 CA $205
CA $253 total
includes taxes & fees
May 24 - May 25
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.
Coffeeville
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place and hosts "
United States
Sonya V.
The price is CA $273
CA $500 total
includes taxes & fees
May 12 - May 13
Cabin in the woods overlooking Grenada lake.

Grenada Lake Resort 2 bedroom Cabin # 6

Grenada Lake Resort 2 bedroom Cabin # 6
Coffeeville
9.6 out of 10, Exceptional, (5 reviews)
"Property was clean and comfortable in a peaceful quiet location."
United States
Christopher C.
The price is CA $220
CA $344 total
includes taxes & fees
May 20 - May 21
Grenada Lake Resort 2 bedroom Cabin # 6

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, (14 reviews)
"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
The price is CA $273
CA $333 total
includes taxes & fees
May 11 - May 12
Minutes away from one of the greatest crappie fishing lakes in the world

Bream Shack-2 bedroom cabin with spacious parking

Bream Shack-2 bedroom cabin with spacious parking
Grenada
8.4 out of 10, Very good, (5 reviews)
"Impeccable!"
United States
Mary W.
The price is CA $191
CA $467 total
includes taxes & fees
May 17 - May 18
Bream Shack-2 bedroom cabin with spacious parking

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, (12 reviews)
"Nice quiet and clean location to share with family and friends"
United States
Janet T.
The price is CA $183
CA $388 total
includes taxes & fees
May 11 - May 12
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

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 CA $239
CA $435 total
includes taxes & fees
May 11 - May 12
The most unique getaway experience in North Mississippi!

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, (3 reviews)
"Amazing cabin, in a great location with a great host"
United States
Conner M.
The price is CA $205
CA $249 total
includes taxes & fees
May 31 - Jun 1
Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters

The Crappie-2 bedroom cabin with spacious parking

The Crappie-2 bedroom cabin with spacious parking
Grenada
10.0 out of 10, Exceptional, (5 reviews)
"Second time staying! GREAT HOST"
United States
Kadeidra R.
The price is CA $205
CA $487 total
includes taxes & fees
May 21 - May 22
The Crappie-2 bedroom cabin with spacious parking

The Bass Shack-2 bedroom cabin w spacious parking

The Bass Shack-2 bedroom cabin w spacious parking
Grenada
9.8 out of 10, Exceptional, (6 reviews)
"The cabin was a perfect place for a getaway or to stay and fish the lake. The property host was very accommodating and helpful with anything we needed. Highly recommend any of her properties, we will be back!"
United States
Jordy B.
The price is CA $191
CA $467 total
includes taxes & fees
May 21 - May 22
The Bass Shack-2 bedroom cabin w spacious parking

Grenada Lake Resort Cabin # 5

Grenada Lake Resort Cabin # 5
Coffeeville
10.0 out of 10, Exceptional, (6 reviews)
"we loved staying her. it was a perfect place to stay. cozy, comfortable, and clean. "
United States
Kevin
The price is CA $131
CA $213 total
includes taxes & fees
May 16 - May 17
Grenada Lake Resort Cabin # 5

Secluded one bedroom cabin with large deck overlooking a wooded gully.

Secluded one bedroom cabin with large deck overlooking a wooded gully.
Grenada
The price is CA $287
CA $595 total
includes taxes & fees
May 21 - May 22
Secluded one bedroom cabin with large deck overlooking a wooded gully.

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

2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
Gore Springs
10.0 out of 10, Exceptional, (7 reviews)
"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.
The price is CA $205
CA $342 total
includes taxes & fees
May 20 - May 21
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake

Magnolia State Winter Escape – Beautiful 3BR Family Home

Magnolia State Winter Escape – Beautiful 3BR Family Home
Grenada
9.2 out of 10, Wonderful, (9 reviews)
"Great atmosphere and great area near downtown Grenada..."
United States
Lelabug G.
The price is CA $209
CA $485 total
includes taxes & fees
May 16 - May 17
Magnolia State Winter Escape – Beautiful 3BR Family Home

Dogwoods-2 bedroom cabin with spacious parking

Dogwoods-2 bedroom cabin with spacious parking
Grenada
9.6 out of 10, Exceptional, (17 reviews)
"Cabin was very clean and comfortable. We’ll be staying there again for sure."
United States
Gabe S.
The price is CA $205
CA $391 total
includes taxes & fees
Jun 1 - Jun 2
Dogwoods-2 bedroom cabin with spacious parking

The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake
Grenada
9.8 out of 10, Exceptional, (17 reviews)
"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.
The price is CA $273
CA $500 total
includes taxes & fees
May 26 - May 27
The Get-A-Way at Grenada lake

House Located Less Than 3 Miles of Grenada Lake

House Located Less Than 3 Miles of Grenada Lake
Coffeeville
9.4 out of 10, Exceptional, (3 reviews)
"Everything was wonderful!!"
United States
anna a.
The price is CA $517
CA $831 total
includes taxes & fees
May 14 - May 15
House Located Less Than 3 Miles of Grenada Lake

Charming family retreat

Charming family retreat
Greenwood
10.0 out of 10, Exceptional, (2 reviews)
"Neat little town. Enjoy our stay"
United States
Robert W.
The price is CA $215
CA $467 total
includes taxes & fees
May 17 - May 18
Charming family retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winona Hotel Reviews

Find out more about Winona

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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, Winona - Montgomery County Library, and Winona City Hall. In the larger area, you’ll find Middleton Cemetery and Winona Country Club.

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.