Sugar Loaf Trailhead Tours and Activities

Plan a trip to see Sugar Loaf Trailhead

Price found within the past 48 hours. Click for updated prices.
Gundersen Hotel & Suites

Gundersen Hotel & Suites

2.5 out of 5
Powell-Poage-Hamilton
Price was CA $1,173, price is now CA $879 per person
CA $879
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to La Crosse (LSE)
9.4/10 Exceptional! (1,002 reviews)
We loved our suite. Easy access to the health care campus makes this the very best option for anyone who might need to be close to the health care facilities.

Reviewed on Mar 6, 2026

The Charmant Hotel

The Charmant Hotel

4 out of 5
Historic Downtown La Crosse
Price was CA $1,368, price is now CA $1,200 per person
CA $1,200
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to La Crosse (LSE)
9.6/10 Exceptional! (1,001 reviews)
Beautiful little hotel with a great bar and restaurant in the perfect location. Everyone was so friendly.

Reviewed on Mar 2, 2026

Fairfield Inn & Suites by Marriott Winona

Fairfield Inn & Suites by Marriott Winona

3 out of 5
Price was CA $1,104, price is now CA $973 per person
CA $973
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Rochester (RST)
9.4/10 Exceptional! (367 reviews)
Everything very was clean, the pillows were decent, the reception was efficient and friendly, bed was so hard I think the carpeted floor would have been softer, there was some minimal noise from Hwy 61, but not too much, breakfast looked good waffle options and a good amount of fresh fruit, the curtains did not cover the windows enough to fully block out the very bright lights outside the hotel. SO, great place if you like a rock hard bed, really awful if, like me and my husband, you need a little cushion on the bed. Neither of us slept at all.

Reviewed on Feb 15, 2026

Popular places to visit

Sugarloaf trail....360 degree views from the top of sugar loaf of the Mississippi River valley. 28 routes for rock climbing to the peak....nice hiking trail to the base!

Sugar Loaf Bluff

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

Sugar Loaf Bluff
Lake Winona Autumn

Lake Park

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.

Lake Park

Winona Health

Though Winona Health might be what brings you to town, perhaps you'll have a chance to explore more of Winona while you are here.

Winona Health

Community Memorial Hospital

Though Community Memorial Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Winona while you are here.

Community Memorial Hospital

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.

Minnesota State College Southeast - Winona Campus

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.

Minnesota State College Southeast

Best Lodging Options Near Sugar Loaf Trailhead

Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
1025 Sugar Loaf Rd Winona MN
Super 8 by Wyndham Winona MN
Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
Express Suites Riverport Inn & Suites
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
1128 Homer Rd Winona MN
Holiday Inn Express & Suites Winona by IHG
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E Winona MN
The Plaza Hotel & Suites Winona
Fairfield Inn & Suites by Marriott Winona

Fairfield Inn & Suites by Marriott Winona

3 out of 5
925 Bruski Drive Winona MN
Fairfield Inn & Suites by Marriott Winona
AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

2.5 out of 5
303 Pelzer Street Winona MN
AmericInn by Wyndham Winona
Alexander Mansion Bed and Breakfast

Alexander Mansion Bed and Breakfast

3.5 out of 5
274 East Broadway Winona MN
Alexander Mansion Bed and Breakfast
Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow

3 out of 5
717 Grand St Winona MN
Big River Escape Parkside Bungalow
Creekside Cabin Getaway

Creekside Cabin Getaway

Winona MN
Creekside Cabin Getaway
See all 380 properties in Sugar Loaf Trailhead
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now