Book Holiday Homes in Winona

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Featured Holiday Homes in Winona

Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.

Coffeeville
The price is NZ$622 per night from 26 Apr to 27 Apr
NZ$622
includes taxes & fees
26 Apr - 27 Apr
Stay at this vacation home in Coffeeville. Enjoy an in-room coffeemaker and air conditioning. Popular attractions South Graysport Public Use Area and Choctaw ...
Cabin in the woods overlooking Grenada lake.
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit

Grenada
Stay at this vacation home in Grenada County. Enjoy a pool table, an in-room coffeemaker, and in-room fireplaces. Popular attraction Magnolia Memorial Roadside ...
5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit
Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown

Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown

2 out of 5
Grenada
Stay at this vacation home in Grenada. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Elizabeth Jones Library and Butler Hill Park are ...
Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown
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Homey Greenwood Getaway w/ Patio & Backyard

Homey Greenwood Getaway w/ Patio & Backyard

Greenwood
Stay at this vacation home in Greenwood. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Greenwood Country ...
Homey Greenwood Getaway w/ Patio & Backyard
Catfish House-1 bedroom with spacious free parking

Catfish House-1 bedroom with spacious free parking

Grenada
Stay at this vacation home in Grenada. Enjoy air conditioning. Popular attractions Wolf Creek Public Use Area and Dogwoods Golf Course are located nearby.
Catfish House-1 bedroom with spacious free parking
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.

Grenada
Book a stay at this business-friendly vacation home in Grenada. Enjoy free WiFi, breakfast (surcharge), and concierge services. Popular attractions North Abutment ...
Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town.
Charming family retreat

Charming family retreat

Greenwood
Stay at this vacation home in Greenwood. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Whittington Park and City Park are located ...
Charming family retreat
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.

Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.

2 out of 5
French Camp
Stay at this vacation home in Montgomery County. Enjoy an in-room coffeemaker, in-room fireplaces, and housekeeping.
Catch and Relax! Private Family friendly house w/ 5 acre fishing pond.
Warm & Inviting home 5 minutes walking distance from restaurants.

Warm & Inviting home 5 minutes walking distance from restaurants.

Greenwood
Stay at this vacation home in Greenwood. Enjoy free WiFi, a garden, and patios. Popular attractions Clerico Park and Greenwood Mall are located nearby.
Warm & Inviting home 5 minutes walking distance from restaurants.
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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.

Winona Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winona vacation homes are the perfect way for you to wing it.

Holiday houses in Winona let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winona in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winona adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winona with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winona vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winona Holiday Homes essential information

Accommodation
12 Holiday Homes
Lowest Price
NZ$161
Highest Price
NZ$622
Popular accommodation
Cabin in the woods overlooking Grenada lake., 5 min. from Grenada Lake! 3 bed room/ Outside pavilion / Family size/ fire pit, Spacious Grenada Brick Home: Perfect Fall Escape. Close to Downtown, Homey Greenwood Getaway w/ Patio & Backyard, Catfish House-1 bedroom with spacious free parking, Rustic log cabin with 5 beds in a private setting, minutes Grenada Lake & town. , Charming family retreat , Catch and Relax! Private Family friendly house w/ 5 acre fishing pond., Warm & Inviting home 5 minutes walking distance from restaurants.

Top trending hotels in Winona

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

2.5 out of 5
413 SE Frontage Road, Winona, MS
Fully refundable
The price is NZ$229 per night from 20 Apr to 21 Apr
NZ$229
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express and Suites Winona North by IHG
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road, Winona, MS
Fully refundableReserve now, pay when you stay
The price is NZ$161 per night from 12 Apr to 13 Apr
NZ$161
includes taxes & fees
12 Apr - 13 Apr
Book a stay at this business-friendly motel in Winona. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
Stay at this motel in Winona. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Winona - Montgomery County Library and Montgomery ...
Relax Inn & Suites
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Holiday Inn Express & Suites Grenada by IHG

Holiday Inn Express & Suites Grenada by IHG

2.5 out of 5
1540 Sunset Dr, Grenada, MS
Fully refundable
The price is NZ$258 per night from 4 May to 5 May
NZ$258
includes taxes & fees
4 May - 5 May
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express & Suites Grenada by IHG
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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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^Subject to availability and chosen travel dates.