The Best Hotels Closest to Sugar Loaf Trailhead in Winona for 2026

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Our top choices for Sugar Loaf Trailhead hotels

Fairfield Inn & Suites by Marriott Winona

0.5 km from Sugar Loaf Trailhead

John

￥22,809 total

includes taxes & fees

Jul 12 - Jul 13

Holiday Inn Express & Suites Winona by IHG

0.5 km from Sugar Loaf Trailhead

Kayla

￥26,113 total

includes taxes & fees

Jul 12 - Jul 13

The Plaza Hotel & Suites Winona

0.5 km from Sugar Loaf Trailhead

James

￥27,015 total

includes taxes & fees

Jul 6 - Jul 7

Express Suites Riverport Inn & Suites

0.4 km from Sugar Loaf Trailhead

Corey

￥19,448 total

includes taxes & fees

Jul 6 - Jul 7

Room, 2 Queen Beds, Non Smoking (Pet-Friendly) | Individually decorated, individually furnished, desk, laptop workspace

Super 8 by Wyndham Winona MN

0.2 km from Sugar Loaf Trailhead

Joshua

￥11,549 total

includes taxes & fees

Jul 7 - Jul 8

Alexander Mansion Bed and Breakfast

Historic Downtown Winona, 2.1 km from Sugar Loaf Trailhead

Theresa

￥20,617 total

includes taxes & fees

Jul 13 - Jul 14

Carriage House B&B

Historic Downtown Winona, 2.3 km from Sugar Loaf Trailhead

Mark

￥22,315 total

includes taxes & fees

Jul 6 - Jul 7

Studio Suite, 1 King Bed, Non Smoking | Desk, blackout drapes, iron/ironing board, free cribs/infant beds

AmericInn by Wyndham Winona

5.8 km from Sugar Loaf Trailhead

Jacob

￥22,196 total

includes taxes & fees

Jul 23 - Jul 24

In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Winona

6 km from Sugar Loaf Trailhead

Twila

￥12,248 total

includes taxes & fees

Jul 19 - Jul 20

Little Bluff Inn

14.8 km from Sugar Loaf Trailhead

Patricia

￥17,356 total

includes taxes & fees

Jul 8 - Jul 9

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Compare popular hotels close to Sugar Loaf Trailhead

Property	Star rating	Guest rating
Fairfield Inn & Suites by Marriott Winona	3.0 star property	9.4 Exceptional 383 reviews	View
Holiday Inn Express & Suites Winona by IHG	2.5 star property	9.2 Wonderful 933 reviews	View
The Plaza Hotel & Suites Winona	3.0 star property	8.8 Excellent 1,002 reviews	View
Express Suites Riverport Inn & Suites	3.0 star property	8.6 Excellent 1,003 reviews	View
Super 8 by Wyndham Winona MN	2.0 star property	7.6 Good 1,000 reviews	View

Top Sugar Loaf Trailhead Hotel Reviews

Bluffside cottage with gorgeous views

10/10 Excellent

"Hill Street House is a beautiful, welcoming, clean, and well appointed cottage with every amenity one needs. Full kitchen and laundry, deck and large windows for view of the river. Communication with the owner was great. I would highly recommend this property... and would book there again if I'm ever in the area."

Little Bluff Inn

10/10 Excellent

"We had an amazing stay at the Little Bluff Inn and I highly recommend the facility! The staff was super friendly and helpful. It was a short walk to the downtown area, parks and hiking trails. The room was so quaint, charming, clean and very well maintained. We are definitely looking forward to a return stay. A big thank you for a wonderful stay!!!"

Victorian era Mississippi riverview retreat.

10/10 Excellent

"A lovely family-style accommodation. Newly renovated with great care. The property includes all necessary modern appliances, cookware, etc. with lovely old-fashioned touches in a historic town, where you can walk to get ice cream! Perfect for a larger family gathering with living space for visiting and a dining area. Thank you for sharing your property with us!"

Hotels near other Sugar Loaf Trailhead attractions

A river winding through a valley with a highway running alongside it.

Sugar Loaf Bluff

9.0/10 (193 reviews)

Learn about the local history of Winona with a stop at Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

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Frequently asked questions

What's the area like around Sugar Loaf Trailhead?

Sugar Loaf Trailhead is located in Winona. Travelers like the surrounding area for its museums. If you're looking for a convenient place to stay, check out the 7 hotels and other accommodations you'll find within a mile.

Where is the best place to stay near Sugar Loaf Trailhead?

Adjacent to Sugar Loaf Trailhead, Express Suites Riverport Inn & Suites is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and a restaurant. Other good choices within a short distance include Super 8 by Wyndham Winona MN and The Plaza Hotel & Suites Winona.

How many hotels can I expect to find near Sugar Loaf Trailhead?

Expedia has 7 hotels and other accommodations within a mile from Sugar Loaf Trailhead.

If I need to cancel the hotel reservation for my stay near Sugar Loaf Trailhead, will I receive a refund?

Yes, you'll find most hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to review the best deals near Sugar Loaf Trailhead.

Where can I learn more about changing or cancelling my trip in the area near Sugar Loaf Trailhead?

For more information about rescheduling or cancelling your stay near Sugar Loaf Trailhead, head over to our customer service page.

What can I see and do near Sugar Loaf Trailhead?

You'll want to browse the collections at Winona County Historical Society, Minnesota Marine Art Museum, and Watkins Heritage Museum. Learn about local history at Merchants Bank and Polish Cultural Institute & Museum Annex. Spend some time wandering around Lake Park, Lake Lodge Recreation Center, and Aghaming Park And Preserve.

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Our top choices for Sugar Loaf Trailhead hotels

Fairfield Inn & Suites by Marriott Winona