Search Vacation Homes in Winona

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Vacation Homes in Winona

Lake Milton Ohio, Lakefront Vacation Rental, 4 Bedrooms, 3 Bath, Private Dock
Fridge, microwave, oven, stovetop

Lake Milton Ohio, Lakefront Vacation Rental, 4 Bedrooms, 3 Bath, Private Dock

9.6 out of 10, Exceptional, (136)
"The house and grounds were beautiful and the lake view was amazing.we all had a great time"
Lake Milton Ohio, Lakefront Vacation Rental, 4 Bedrooms, 3 Bath, Private Dock
Lakeside Paradise on Berlin
Fridge, microwave, oven, stovetop

Lakeside Paradise on Berlin

10.0 out of 10, Exceptional, (91)
"We really enjoyed our stay. The setup was nice and sunrise was gorgeous! We would definitely stay here again when visiting the area."
$287 nightly
The price is $299
Aug 25 - Aug 26
Total includes taxes and fees
Lakeside Paradise on Berlin
Stien Oasis: Heated Indoor Pool Oasis With Theater, Bar&Tennis Court.
Fridge, microwave, oven, stovetop

Stien Oasis: Heated Indoor Pool Oasis With Theater, Bar&Tennis Court.

10.0 out of 10, Exceptional, (12)
"Mi family and I had a great time there"
$1,734 nightly
The price is $1,795
Sep 9 - Sep 10
Total includes taxes and fees
Stien Oasis: Heated Indoor Pool Oasis With Theater, Bar&Tennis Court.
The Victorian House - Four Bedrooms - Two Bathrooms -
Exterior

The Victorian House - Four Bedrooms - Two Bathrooms -

10.0 out of 10, Exceptional, (1)
"I will recommend and stay at the property again when I am in the area. Beautiful house and nicely decorated. "
The Victorian House - Four Bedrooms - Two Bathrooms -
Sweet Louie's Lake House
Fridge, microwave, oven, stovetop

Sweet Louie's Lake House

9.4 out of 10, Exceptional, (12)
"Beautiful and peaceful getaway at the lake with a view that no picture could ever possibly do any justice. Reasonably close proximity to great food options and 2 decent dog parks as well. Host is very responsive and helpful as well. Thank you for having us! "
Sweet Louie's Lake House
Beautiful 3 Bedroom Downtown Salem Home
Fridge, microwave, oven, stovetop

Beautiful 3 Bedroom Downtown Salem Home

10.0 out of 10, Exceptional, (4)
"Was a great place to stay while visiting family"
$301 nightly
The price is $311
Aug 22 - Aug 23
Total includes taxes and fees
Beautiful 3 Bedroom Downtown Salem Home
WinklerWald- 6 BR family retreat
Fridge, microwave, oven, stovetop

WinklerWald- 6 BR family retreat

10.0 out of 10, Exceptional, (10)
"We had a fantastic time with our friends. The house and property were great. The kitchen was well stocked and our host, Mike was very friendly and responsive. We would definitely come back. "
WinklerWald- 6 BR family retreat
Lakeside Acres at Berlin Lake, OH - 4 Bedroom/3 Bath with separable studio apt
Property grounds

Lakeside Acres at Berlin Lake, OH - 4 Bedroom/3 Bath with separable studio apt

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place was awesome and the host answered every time I sent an email. Definitely will stay here again. "
Lakeside Acres at Berlin Lake, OH - 4 Bedroom/3 Bath with separable studio apt
Wayside Getaway with cozy patio & private hot tub!
Fridge, microwave, oven, stovetop

Wayside Getaway with cozy patio & private hot tub!

10.0 out of 10, Exceptional, (4)
"Jason is very easy to work with, from booking to check out it was a breeze. This is our second time staying here while our granddaughter competes in the barrel racing youth championships at Garwood Arena. Would definitely recommend!"
Wayside Getaway with cozy patio & private hot tub!
Cozy, Farmview Bungalow, with Central Location!
Exterior

Cozy, Farmview Bungalow, with Central Location!

10.0 out of 10, Exceptional, (15)
"The house was very nice, clean and set up very well. I would definitely recommend a stay here."
Cozy, Farmview Bungalow, with Central Location!
Pet-Friendly Charming & Cozy 3-bedroom house AC & WiFi in pleasant Youngstown
Private kitchen

Pet-Friendly Charming & Cozy 3-bedroom house AC & WiFi in pleasant Youngstown

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location. Nicely remodeled, very comfortable. Host is very responsive. "
Pet-Friendly Charming & Cozy 3-bedroom house AC & WiFi in pleasant Youngstown
Quaint Youngstown Home ~ 2 Mi to Boardman Park!
Fridge, microwave, stovetop, coffee/tea maker

Quaint Youngstown Home ~ 2 Mi to Boardman Park!

Quaint Youngstown Home ~ 2 Mi to Boardman Park!
Retreat on Lake Milton 2 bed
Exterior

Retreat on Lake Milton 2 bed

9.4 out of 10, Exceptional, (6)
"We had a very relaxing time and felt comfortable."
Retreat on Lake Milton 2 bed
Luxury Timber Lodge w/Hot Tub-Sleeps 20
7 bedrooms, desk, iron/ironing board, travel crib

Luxury Timber Lodge w/Hot Tub-Sleeps 20

9.8 out of 10, Exceptional, (28)
"We greatly enjoyed our stay. We had so much space for our large family and truly enjoyed the cabin escape."
Luxury Timber Lodge w/Hot Tub-Sleeps 20
North Jackson Vacation Rental w/ Wraparound Deck!
Highchair, cookware/dishes/utensils

North Jackson Vacation Rental w/ Wraparound Deck!

10.0 out of 10, Exceptional, (8)
"Met up with a friend here and the stay was seamless— easy check-in, great communication with the owner, very clean, and well appointed."
North Jackson Vacation Rental w/ Wraparound Deck!
Sleeps 8, YSU, Fairgrounds, Wi-Fi, EV1, Remote
Fridge, microwave, oven, stovetop

Sleeps 8, YSU, Fairgrounds, Wi-Fi, EV1, Remote

7.0 out of 10, Good, (2)
"Was a very convenient location the homeowners were very friendly and was super helpful and it was a very easy stay."
$364 nightly
The price is $389
Aug 14 - Aug 15
Total includes taxes and fees
Sleeps 8, YSU, Fairgrounds, Wi-Fi, EV1, Remote
Century Home
Interior

Century Home

9.8 out of 10, Exceptional, (7)
"Century House is gorgeous. Andy and Amanda have done a great job with this home. Highly recommend!"
$367 nightly
The price is $381
Aug 14 - Aug 15
Total includes taxes and fees
Century Home
Pet Friendly 4 bedroom home in Alliance!
Exterior detail

Pet Friendly 4 bedroom home in Alliance!

Pet Friendly 4 bedroom home in Alliance!
Cozy Lake House with a VIEW
Terrace/patio

Cozy Lake House with a VIEW

Cozy Lake House with a VIEW
Charming, Boutique Hotel with 21 newly renovated rooms!
Interior

Charming, Boutique Hotel with 21 newly renovated rooms!

Charming, Boutique Hotel with 21 newly renovated rooms!
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
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Hampton Inn & Suites Youngstown-Canfield

Hampton Inn & Suites Youngstown-Canfield

10/10 Excellent
"Friendly Staff"
William 7-night trip
Posted 1 day ago
Hampton Inn & Suites Youngstown-Canfield