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

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 prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Sugar Loaf Trailhead hotels

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

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

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

1. Fairfield Inn & Suites by Marriott Winona

0.5 km from Sugar Loaf Trailhead

Stephanie

AED 493

AED 550 total

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

AED 577

AED 644 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A spacious living area with leather sofas, a coffee table with magazines, and a stone fireplace.

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

3. The Plaza Hotel & Suites Winona

0.5 km from Sugar Loaf Trailhead

Christopher

AED 533

AED 595 total

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 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.

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

4. Express Suites Riverport Inn & Suites

0.4 km from Sugar Loaf Trailhead

Sasha

AED 441

AED 492 total

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.

A breakfast area with a wooden wall, a clock, and a coffee machine.

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

AED 208

AED 237 total

includes taxes & fees

1 Nov - 2 Nov

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

A gym with treadmills, an elliptical, and a stationary bike.

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

6. Days Inn by Wyndham Winona

6 km from Sugar Loaf Trailhead

William

AED 250

AED 279 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Compare popular hotels close to Sugar Loaf Trailhead

Property	Property class	Guest rating
Fairfield Inn & Suites by Marriott Winona	9.4 Exceptional 408 reviews	View
Holiday Inn Express & Suites Winona by IHG	9.2 Wonderful 966 reviews	View
The Plaza Hotel & Suites Winona	8.6 Excellent 1,001 reviews	View
Express Suites Riverport Inn & Suites	8.4 Very good 1,001 reviews	View
Super 8 by Wyndham Winona MN	7.6 Good 1,007 reviews	View

Top Sugar Loaf Trailhead Hotel Reviews

The Rushford Inn

10/10 Excellent

"Room was very clean and neat"

Express Suites Riverport Inn & Suites

10/10 Excellent

"We alway stay at Riverport when in Winona! Staff is kind and the breakfast is great! And it’s in close proximity to campus!"

Little Bluff Inn

10/10 Excellent

"Wonderful family run boutique hotel."

Super 8 by Wyndham Winona MN

8/10 Good

"Good Price. Clean room. Breakfast"

Cabin on the Mississippi River

10/10 Excellent

"Enjoyed the pillows"

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."

Studio Cottage at Lake Road Campground, on the beautiful Mississippi River.

10/10 Excellent

"What a perfect place to spend a weekend exploring La Crosse and the beautiful Mississippi River area! My bestie and I loved the cozy cottage and the peaceful campground. It would have been helpful to know when we booked the cottage that we would need to bring our own sheets, pillows, blanket, and towels, but that wasn't a problem. The fire ring was a nice bonus; great for cool evenings. We will stay again!"

Days Inn by Wyndham Winona

10/10 Excellent

"clean rooms and nice breakfast"

Secluded Modern Cabin with Bluff Views, Hot Tub, Fire Pit.

10/10 Excellent

"We had a wonderful visit. We spend most of our time outdoors and enjoyed quite a few fires in the smokeless firepit along with using the hottub which appears clean and well maintained. It is a serene and private property, perfect for us to take a weekend getaway to unwind. We didn't need to contact the host for anything during our stay, but beforehand he was very responsive with the couple of questions I had. We would recommend to a friend and may stay here again in the future."

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 with a stop at Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

See properties

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.

See properties

Minnesota State College Southeast - Winona Campus

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

See properties

Minnesota State College Southeast

Enjoy the collegiate vibe at Minnesota State College Southeast during your stay in Winona. Stroll along the riverfront or experience the area's museums.

See properties

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.

See properties

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.

See properties

St. Stanislaus Kostka Basilica

Find out about the history of Winona with a stop at St. Stanislaus Kostka Basilica. Stroll along the riverfront or experience the area's museums.

See properties

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.

See properties

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

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sugar Loaf Trailhead hotels

1. Fairfield Inn & Suites by Marriott Winona