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Top Holiday Rentals in Winona

Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.
9.4 out of 10, Exceptional, (45)
"Check in was super easy and owner was easy going. The house was spacious and accommodations were great. Nice private area with fenced in yard. 5 mins away from the lake or any of the restaurants. Can’t wait to make another trip to Grenada again and will gladly stay in the same house."
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.
Grenada Lake Resort Cabin # 5
10.0 out of 10, Exceptional, (5)
"Great time and a great place to stay. I just wish it was a little closer to places to eat."
The price is £129
includes taxes & fees
9 Jun - 10 Jun
Grenada Lake Resort Cabin # 5
Cabin in the woods overlooking Grenada lake.
10.0 out of 10, Exceptional, (19)
"The cabin was perfect. The property is peaceful and beautiful. We enjoyed morning coffee on the porch listening to the birds. We walked around the property a bit and found a big old turtle shell in the woods that we left on the back porch. I wish we would’ve stayed a few more nights. Certainly is a great place to relax and unwind. "
The price is £290
includes taxes & fees
6 Jun - 7 Jun
Cabin in the woods overlooking Grenada lake.
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Grenada Lake Resort Cabin # 1
The price is £129
includes taxes & fees
7 Jun - 8 Jun
Grenada Lake Resort Cabin # 1
Minutes away from one of the greatest crappie fishing lakes in the world
10.0 out of 10, Exceptional, (4)
"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! "
The price is £193
includes taxes & fees
7 Jun - 8 Jun
Minutes away from one of the greatest crappie fishing lakes in the world
Dogwoods-2 bedroom cabin with spacious parking
10.0 out of 10, Exceptional, (3)
"We were happy with our surroundings the moment we drove up to our cabin in the woods. It was so pretty and peaceful. The birds sang to us while we sat on the front porch drinking hot chocolate in the evening, and woke us with songs the next morning. The cabin was very nicely furnished, with a comfortable reclining chair and sofa in the living room, a fully stocked kitchen, large walk in shower, and a queen sized bed that was perfect for a great night’s sleep. We didn’t use the second bedroom...
The price is £140
includes taxes & fees
12 Jun - 13 Jun
Dogwoods-2 bedroom cabin with spacious parking
The Bass Shack-2 bedroom cabin w spacious parking
10.0 out of 10, Exceptional, (1)
"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!"
The price is £168
includes taxes & fees
9 Jun - 10 Jun
The Bass Shack-2 bedroom cabin w spacious parking
House Located Less Than 3 Miles of Grenada Lake
10.0 out of 10, Exceptional, (1)
"Racing"
The price is £482
includes taxes & fees
9 Jun - 10 Jun
House Located Less Than 3 Miles of Grenada Lake
Grenada Lake Resort Cabin # 3
10.0 out of 10, Exceptional, (1)
"Very secluded"
The price is £129
includes taxes & fees
7 Jun - 8 Jun
Grenada Lake Resort Cabin # 3
Modern Greenwood Studio < 1 Mi to Downtown!
3.5 star property
Modern Greenwood Studio < 1 Mi to Downtown!
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
10.0 out of 10, Exceptional, (7)
"Good space inside and outside for our small group gathering. Plenty of seating for everyone to enjoy the outdoors area. Conveniently located near Grenada Lake. Everyone in our group enjoyed our entire stay. The property is exactly as described. The check-in was super simple. The property offers lots of parking. We had 4 trucks and a boat. We will definitely be returning! Thanks for the southern hospitality!!!"
The price is £276
includes taxes & fees
11 Jun - 12 Jun
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Homey Greenwood Getaway w/ Patio & Backyard
10.0 out of 10, Exceptional, (3)
"Not far from anything easy to get to"
Homey Greenwood Getaway w/ Patio & Backyard
Minutes to Grenada Lake, Restaurants, and Golf Courses.
10.0 out of 10, Exceptional, (1)
"Alvin was a great host, we ran late getting there, Alvin called to check on us. Helped with detailed instructions. Actually waited up on us past his bedtime. He was there each time we came off the lake, shared stories. He treats you in a manner that makes you relaxed and feel welcome. His location is away from traffic, yet close to docks and restaurants. Definitely consider for the peace and quiet, much preferred over hotel room. Great stay."
The price is £171
includes taxes & fees
5 Jun - 6 Jun
Minutes to Grenada Lake, Restaurants, and Golf Courses.
The Crappie-2 bedroom cabin with spacious parking
10.0 out of 10, Exceptional, (1)
"The property was clean and the driveway was nice for pulling two boats into it with plenty of room. Owner was friendly when I had to contact them about the door code. Great little cabin to rent."
The price is £195
includes taxes & fees
8 Jun - 9 Jun
The Crappie-2 bedroom cabin with spacious parking
Homey Greenwood Getaway w/ Patio & Backyard
3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
The price is £333
includes taxes & fees
10 Jun - 11 Jun
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Grenada Lake Resort Cabin # 2
10.0 out of 10, Exceptional, (1)
"Nice quite area cozy and rustic interior of the cabin "
The price is £129
includes taxes & fees
5 Jun - 6 Jun
Grenada Lake Resort Cabin # 2
Grenada Lake Resort Cabin # 4
The price is £129
includes taxes & fees
8 Jun - 9 Jun
Grenada Lake Resort Cabin # 4
Modern Greenwood Studio < 1 Mi to Downtown!
10.0 out of 10, Exceptional, (4)
"Great little studio rental. There was a delay in the check in code being sent and I would recommend adjusting the shower door. My wife was locked in while a was a the grocery store. "
Modern Greenwood Studio < 1 Mi to Downtown!
Greenwood Studio Cottage < 1 Mi to Downtown!
10.0 out of 10, Exceptional, (1)
Greenwood Studio Cottage < 1 Mi to Downtown!
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See all available properties in Winona
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.

Other types of properties in Winona you may be interested in

Holiday Inn Express and Suites Winona North, an IHG Hotel
2.5 star property
8.2 out of 10, Very good, (534)
"Its location "
The price is £120
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn Express and Suites Winona North, an IHG Hotel
Americas Best Value Inn Winona
2.0 star property
8.0 out of 10, Very good, (325)
"Bathroom too small,,, i fell no saftey features 😒 otherwise everything was outstanding the staff was helpful and courteous wonderful,,, cannot stay again or recommend because of the bathroom"
The price is £81
includes taxes & fees
5 Jun - 6 Jun
Americas Best Value Inn Winona
Relax Inn & Suites
2.0 star property
5.2 out of 10, (29)
"The prices are reasonable. It’s not the Hilton but it’s definitely worth a stay. Will be staying again. "
The price is £60
includes taxes & fees
5 Jun - 6 Jun
Relax Inn & Suites
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.

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as £129 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 holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay. Winona is known for its coffee shops 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 holiday rentals that Winona has to offer?

Cozy home away from home!: This highly rated holiday home rental in Winona offers 1 hot tub, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Winona?

Take time out to visit local sights such as Winona Country Club, Montgomery County Performing Arts Center, and Middleton Cemetery. In the wider area, you’ll also find Grenada Country Club.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip.

Recent reviews of Winona properties
Expedia verified reviews