⭐ Top 10 Hotels Near Sugar Loaf Trailhead for 2026

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Our top choices for Sugar Loaf Trailhead hotels

A modern hotel lobby with a dining area, seating arrangements, and a stone fireplace.

An outdoor patio area with stone walls, a stone fireplace, and multiple tables and chairs.

A hotel with a modern design, featuring a stone facade and a covered entrance.

1. Fairfield Inn & Suites by Marriott Winona

0.5 km from Sugar Loaf Trailhead

Stephanie

S$191

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a blue sofa, a wooden coffee table, a lamp, a TV, and a door leading to a balcony.

A hotel indoor pool with clear water, lounge chairs, and a seating area with an umbrella.

2. Holiday Inn Express & Suites Winona by IHG

0.5 km from Sugar Loaf Trailhead

Kristie

S$220

includes taxes & fees

4 Oct - 5 Oct

An outdoor seating area with brick walls, green railings, and hanging flower baskets.

A pool with a large, colorful fish-shaped slide.

A bar area with wooden chairs and tables, a bar counter with bottles and glasses, and a television screen displaying a sports game.

A hotel with a central clock tower, multiple windows, and a parking lot with cars.

3. The Plaza Hotel & Suites Winona

0.5 km from Sugar Loaf Trailhead

Christopher

S$207

includes taxes & fees

1 Nov - 2 Nov

A hotel pool area with multiple lounge chairs, a pool, and a second-floor balcony with windows.

A bar area with wooden bar stools, a counter, and a menu board.

A brick building with a sign reading "Riverport Inn & Suites" and two flags.

A spacious lobby with a stone fireplace, leather seating, a staircase with glass railings, and a view of the outside through large windows.

4. Express Suites Riverport Inn & Suites

0.4 km from Sugar Loaf Trailhead

Sasha

S$171

includes taxes & fees

4 Oct - 5 Oct

A hotel room with two beds, a desk with a chair, a TV, and a large waterfall painting on the wall.

A hotel room with large windows, a clock, and framed pictures on the walls.

An outdoor patio with a table and chairs, a red umbrella, and a view of trees and a sunset.

A reception area with a modern design, featuring a check-in counter, a door, and a small seating area with red stools.

5. Super 8 by Wyndham Winona MN

0.2 km from Sugar Loaf Trailhead

William

S$82

includes taxes & fees

1 Nov - 2 Nov

A park with picnic tables and chairs, a large tree, and a lake in the background.

A kitchen with grey cabinets, a wooden countertop, a built-in sink, and a tiled backsplash.

A window with a view of a snowy outdoor area, including a red car and a small Christmas tree.

A room with a fireplace, a fan, and a framed picture on the wall.

6. Little Bluff Inn

14.8 km from Sugar Loaf Trailhead

Patricia

S$137

includes taxes & fees

29 Oct - 30 Oct

A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a large mirror.

An indoor swimming pool with clear water, a lifeguard on duty sign, and a seating area with chairs and tables.

A multi-story hotel with a prominent "American" sign, a parking lot with several cars, and a landscaped entrance area.

A hotel room with a sofa, a small table, a TV, a microwave, and a door.

7. AmericInn by Wyndham Winona

5.8 km from Sugar Loaf Trailhead

SANDRA

S$169

includes taxes & fees

11 Oct - 12 Oct

A hotel room with two beds, a large landscape painting above the headboard, a bedside table with a phone, and a blue patterned rug.

A breakfast area with a coffee station, a refrigerator, and a dining table with chairs.

A modern room with two sofas, a coffee table, and large windows with curtains.

A reception area with a counter, a clock, a desk with a computer, and a framed picture on the wall.

8. Days Inn by Wyndham Winona

6 km from Sugar Loaf Trailhead

William

S$97

includes taxes & fees

1 Nov - 2 Nov

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Compare popular hotels close to Sugar Loaf Trailhead

Property	Property class	Guest rating
Fairfield Inn & Suites by Marriott Winona	9.4 Exceptional 407 reviews	View
Holiday Inn Express & Suites Winona by IHG	9.2 Wonderful 966 reviews	View
The Plaza Hotel & Suites Winona	8.6 Excellent 1,000 reviews	View
Express Suites Riverport Inn & Suites	8.4 Very good 1,000 reviews	View
Super 8 by Wyndham Winona MN	7.6 Good 1,007 reviews	View

Top Sugar Loaf Trailhead Hotel Reviews

Little Bluff Inn

10/10 Excellent

"It was Perfect for a get away! The rooms were large with a table and chairs, small kitchen but all we needed. The owners were very nice and shared the history of the Inn with us. It was quiet and the view was beautiful!"

Stoney Creek Hotel La Crosse - Onalaska

8/10 Good

"."

GrandStay Hotel & Suites

10/10 Excellent

"Super friendly and helpful staff! Thank you!"

Super 8 by Wyndham Winona MN

8/10 Good

"Good Price. Clean room. Breakfast"

Country Inn & Suites by Radisson, La Crosse, WI

8/10 Good

"Breakfast buffet was not monitored well enough. Out of a few of popular items both mornings"

Fairfield Inn & Suites by Marriott Winona

10/10 Excellent

"Rooms are clean and front desk staff were amazing."

Prairie Inn and Suites Holmen/La Cross

10/10 Excellent

"This place is a gem. And, for the price it is unbelievable! The staff is very pleasant and warm. The facility is well maintained, extremely clean and overall just a rare pleasure for a simple, unpretentious establishment. Highly recommend in every respect."

Alexander Mansion Bed and Breakfast

10/10 Excellent

"Staying at the Alexander Mansion was like stepping back in time to a unique era in Winona history. Our host is very knowledgeable, welcoming and gracious. We were very impressed by all the attention to detail, the delicious breakfast, the lovely rooms and all the special touches that made this an amazing and memorable visit. Thank you so much."

Express Suites Riverport Inn & Suites

10/10 Excellent

"Friendly staff, quiet environment. My son particularly liked the pool."

Other attractions near Sugar Loaf Trailhead

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 when you take a trip to Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

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A calm lake reflecting yellow and green trees, surrounded by a forested hillside.

Lake Park

9.0/10 (43 reviews)

Lake Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's museums.

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Minnesota State College Southeast - Winona Campus

Explore the campus of Minnesota State College Southeast - Winona Campus during your visit to Winona. Stroll along the riverfront or experience the area's museums.

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Minnesota State College Southeast

Enjoy the student vibe at Minnesota State College Southeast as part of your travels around Winona. Stroll along the riverfront or experience the area's museums.

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Sobieski Park

Sobieski Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's museums.

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Gabrych Park

Gabrych Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's museums.

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St. Stanislaus Kostka Basilica

Find out about the history of Winona when you spend time at St. Stanislaus Kostka Basilica. Stroll along the riverfront or experience the area's museums.

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Lake Lodge Recreation Center

8.0/10 (32 reviews)

Explore the great outdoors at Lake Lodge Recreation Center, a lovely green space in Winona. 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. Travellers like the surrounding area for its museums. If you're looking for a convenient place to stay, take a look at the 7 hotels and other accommodation options 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 traveller 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 accommodation options 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, most hotel room reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within 24 hours of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get the best deals available near Sugar Loaf Trailhead.

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 Polish Cultural Institute & Museum Annex and Merchants Bank. Spend some time wandering around Lake Park, Lake Lodge Recreation Center and Garvin Heights City Park.

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Our top choices for Sugar Loaf Trailhead hotels

1. Fairfield Inn & Suites by Marriott Winona