Winona Vacation Rentals

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In two weeks
Sep 19 - Sep 21
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Oct 3 - Oct 5
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Nov 28 - Nov 30

Vacation Rentals in Winona

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 CA $342
CA $427 total
includes taxes & fees
Sep 4 - Sep 5
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 CA $206
CA $255 total
includes taxes & fees
Sep 4 - Sep 5
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

The price is CA $481
CA $600 total
includes taxes & fees
Sep 4 - Sep 5
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 CA $241
CA $412 total
includes taxes & fees
Sep 10 - Sep 11
The most unique getaway experience in North Mississippi!
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 CA $275
CA $505 total
includes taxes & fees
Sep 4 - Sep 5
The Get-A-Way at Grenada lake
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
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)
"House and property are very nice, and well maintained. The outside recreation area has everything for a great time for all ages. 100% plan on making this a yearly getaway for the family. "
The price is CA $688
CA $1,261 total
includes taxes & fees
Sep 4 - Sep 5
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Grenada Lake Resort Cabin # 5
Interior

Grenada Lake Resort Cabin # 5

10.0 out of 10, Exceptional, (6)
"we loved staying her. it was a perfect place to stay. cozy, comfortable, and clean. "
The price is CA $132
CA $215 total
includes taxes & fees
Sep 4 - Sep 5
Grenada Lake Resort Cabin # 5
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 CA $275
CA $505 total
includes taxes & fees
Sep 5 - Sep 6
Cabin in the woods overlooking Grenada lake.
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 CA $193
CA $451 total
includes taxes & fees
Sep 4 - Sep 5
Bream Shack-2 bedroom cabin with spacious parking
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 CA $206
CA $467 total
includes taxes & fees
Sep 5 - Sep 6
The Crappie-2 bedroom cabin with spacious parking
Dogwoods-2 bedroom cabin with spacious parking
Fridge, microwave, oven, stovetop

Dogwoods-2 bedroom cabin with spacious parking

9.4 out of 10, Exceptional, (13)
"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 CA $206
CA $367 total
includes taxes & fees
Sep 4 - Sep 5
Dogwoods-2 bedroom cabin with spacious parking
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 CA $217
CA $469 total
includes taxes & fees
Sep 6 - Sep 7
Charming family retreat
Grenada Lake Resort Cabin # 2
Interior

Grenada Lake Resort Cabin # 2

10.0 out of 10, Exceptional, (2)
"Nice quite area cozy and rustic interior of the cabin "
The price is CA $132
CA $215 total
includes taxes & fees
Sep 4 - Sep 5
Grenada Lake Resort Cabin # 2
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
House Located Less Than 3 Miles of Grenada Lake
Private kitchen

House Located Less Than 3 Miles of Grenada Lake

9.0 out of 10, Wonderful, (2)
"We had a wonderful stay. It was very quiet location out in the country. It was roomy with plenty of parking for the family. "
The price is CA $520
CA $836 total
includes taxes & fees
Sep 4 - Sep 5
House Located Less Than 3 Miles of 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 CA $185
CA $388 total
includes taxes & fees
Sep 4 - Sep 5
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Grenada Lake Resort Cabin # 4
Interior

Grenada Lake Resort Cabin # 4

9.0 out of 10, Wonderful, (2)
"Very nice cabin although a little smaller than expected. Road into cabin could use some work."
The price is CA $132
CA $215 total
includes taxes & fees
Sep 4 - Sep 5
Grenada Lake Resort Cabin # 4
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
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

Find out more about Winona

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona vacation rentals we have selected for you start as low as CA $132 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.