Search Hotels with Pool in Winona

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 availability on Winona Hotels with Pool

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winona hotels with a pool

Outdoor pool
Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG
2.5 star property
Winona
8.2 out of 10, Very good, (676)
"Friendly staff that made our stay feel comfortable and like staying with friends."
United States
Jennifer
The price is ฿3,453
฿3,764 total
includes taxes & fees
16 Jan - 17 Jan 2026
Holiday Inn Express and Suites Winona North by IHG
Outdoor pool
Americas Best Value Inn Winona

Americas Best Value Inn Winona

Americas Best Value Inn Winona
2.0 star property
Winona
8.0 out of 10, Very good, (461)
"Friendly staff, clean and quite room safe area "
United States
Braeden
The price is ฿3,077
฿3,354 total
includes taxes & fees
25 Jan - 26 Jan 2026
Americas Best Value Inn Winona
Seasonal outdoor pool
Holiday Inn Express & Suites Grenada by IHG

Holiday Inn Express & Suites Grenada by IHG

Holiday Inn Express & Suites Grenada by IHG
2.5 star property
Grenada
8.8 out of 10, Excellent, (551)
"Everything you want In a room"
United States
Nicklaus
The price is ฿3,079
฿3,387 total
includes taxes & fees
16 Jan - 17 Jan 2026
Holiday Inn Express & Suites Grenada by IHG
Outdoor pool
Econo Lodge Grenada

Econo Lodge Grenada

Econo Lodge Grenada
2.0 star property
Grenada
8.4 out of 10, Very good, (217)
"Very convenient location; polite staff"
United States
Jane
The price is ฿2,321
฿2,554 total
includes taxes & fees
15 Jan - 16 Jan 2026
Econo Lodge Grenada
Seasonal outdoor pool, pool loungers
Baymont by Wyndham Grenada

Baymont by Wyndham Grenada

Baymont by Wyndham Grenada
2.5 star property
Grenada
6.2 out of 10, (664)
"Good trip"
United States
Paula
The price is ฿2,268
฿2,494 total
includes taxes & fees
30 Dec - 31 Dec
Baymont by Wyndham Grenada
Seasonal outdoor pool, pool umbrellas, pool loungers
SureStay Plus Hotel by Best Western Greenwood

SureStay Plus Hotel by Best Western Greenwood

SureStay Plus Hotel by Best Western Greenwood
2.5 star property
Greenwood
8.2 out of 10, Very good, (694)
"I was impressed during my stay. The staff was very welcoming and extremely professional. The rooms were spotless and comfortable. I enjoyed the amenities, too. Highly recommend whether for a short or long stay."
United States
Patricia
The price is ฿3,949
฿4,265 total
includes taxes & fees
25 Jan - 26 Jan 2026
SureStay Plus Hotel by Best Western Greenwood
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

Top Winona Hotel Reviews

Motel 6 Greenwood, MS

Motel 6 Greenwood, MS

10/10 Excellent
"Very clean room, good outside lighting at night, and a very competitive price...I'll will be staying there again really soon!! "
Bernard 1-night trip
Posted 10 days ago
Motel 6 Greenwood, MS

Frequently asked questions

What are some accommodation options with pools in Winona?
Holiday Inn Express and Suites Winona North by IHG: Features continental, an outdoor pool and complimentary high-speed (wired) Internet access. Americas Best Value Inn Winona: Offers daily, an outdoor pool and free self parking. Relax Inn & Suites: Offers a children's pool, a seasonal outdoor pool and full. Comfort Inn & Suites Grenada: Offers daily, a seasonal outdoor pool and free self parking. SureStay Plus Hotel by Best Western Greenwood: Provides full, a seasonal outdoor pool and free self parking.
What is there to see and do in Winona?
During your stay, visit sights such as Montgomery County Performing Arts Center, Winona - Montgomery County Library and Winona City Hall.
When is the best time to book a hotel with a pool in Winona?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Winona in the hottest months of July, August or June, when the average temp is 26°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 9°C.