Holiday rentals near Sugar Loaf Trailhead
We found 101 holiday rentals — enter your dates for availability
If you'd like to stay close to Sugar Loaf Trailhead, take a look at private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the amenities that you need and want, which might include Wi-Fi and a fireplace. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Sugar Loaf Trailhead
Showing deals for:7 Nov - 14 Nov
Image gallery for Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
1010 out of 10 rating
Exceptional
(17 reviews)
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Winona, MN
9% off
Price is S$2,489
S$2,489
S$356 per night
includes taxes & fees
Image gallery for Come Stay like Kings and Queens in this Castle style Home- Beautiful and Private
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Come Stay like Kings and Queens in this Castle style Home- Beautiful and Private
La Crescent, MN
8% off
Price is S$5,781
S$5,781
S$826 per night
includes taxes & fees
Image gallery for Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
1010 out of 10 rating
Exceptional
(10 reviews)
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
Winona, MN
17% off
Price is S$1,475
S$1,475
S$211 per night
includes taxes & fees
Image gallery for Grand home with views of the Mississippi!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Grand home with views of the Mississippi!
Trempealeau, WI
7% off
Price is S$3,091
S$3,091
S$442 per night
includes taxes & fees
Image gallery for The Exchange 12 | Historic Bldg, 1 BR ADA, Dwntwn
1010 out of 10 rating
Exceptional
(6 reviews)
The Exchange 12 | Historic Bldg, 1 BR ADA, Dwntwn
Winona, MN
8% off
Price is S$1,619
S$1,619
S$231 per night
includes taxes & fees
Image gallery for Cabin on the Mississippi River
1010 out of 10 rating
Exceptional
(77 reviews)
Cabin on the Mississippi River
Trempealeau, WI
8% off
Price is S$1,891
S$1,891
S$270 per night
includes taxes & fees
Image gallery for Charming Home: 3 Blocks to Winona State University
1010 out of 10 rating
Exceptional
(7 reviews)
Charming Home: 3 Blocks to Winona State University
Winona, Minnesota
13% off
Price is S$1,598
S$1,598
S$228 per night
includes taxes & fees
Image gallery for The Bungaleau 1 Bedroom House In Cute Rivertown
9.89.8 out of 10 rating
Exceptional
(82 reviews)
The Bungaleau 1 Bedroom House In Cute Rivertown
Trempealeau, WI
8% off
Price is S$1,381
S$1,381
S$197 per night
includes taxes & fees
Image gallery for Cozy cabin 25 minutes from La Crosse,Winona & Arcadia.Overlooks the Black River!
9.09.0 out of 10 rating
Wonderful
(16 reviews)
Cozy cabin 25 minutes from La Crosse,Winona & Arcadia.Overlooks the Black River!
Galesville, WI
13% off
Price is S$1,495
S$1,495
S$214 per night
includes taxes & fees
Image gallery for Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
1010 out of 10 rating
Exceptional
(7 reviews)
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Winona, MN
8% off
Price is S$8,725
S$8,725
S$1,246 per night
includes taxes & fees
Image gallery for Looking to get away from it all?
1010 out of 10 rating
Exceptional
(136 reviews)
Looking to get away from it all?
Fountain City, WI
9% off
Price is S$1,607
S$1,607
S$230 per night
includes taxes & fees
Image gallery for Lower Level Amelia’s Place
8.88.8 out of 10 rating
Excellent
(6 reviews)
Lower Level Amelia’s Place
Lewiston, MN
8% off
Price is S$1,267
S$1,267
S$181 per night
includes taxes & fees
Image gallery for Beautiful Cozy Lake House on 2 & 1/2 acres!
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Beautiful Cozy Lake House on 2 & 1/2 acres!
Galesville, WI
12% off
Price is S$1,540
S$1,540
S$220 per night
includes taxes & fees
Image gallery for Vintage Lustron Home Piece of History
1010 out of 10 rating
Exceptional
(20 reviews)
Vintage Lustron Home Piece of History
Minnesota City, MN
8% off
Price is S$1,510
S$1,510
S$216 per night
includes taxes & fees
Image gallery for A fully modeled home overlooking Mississippi River in a charming river town.
9.89.8 out of 10 rating
Exceptional
(55 reviews)
A fully modeled home overlooking Mississippi River in a charming river town.
Trempealeau, WI
6% off
Price is S$3,745
S$3,745
S$535 per night
includes taxes & fees
Image gallery for The Exchange 16 | Historic Bldg, Studio, Dwntwn
9.69.6 out of 10 rating
Exceptional
(13 reviews)
The Exchange 16 | Historic Bldg, Studio, Dwntwn
Winona, MN
8% off
Price is S$1,357
S$1,357
S$194 per night
includes taxes & fees
Image gallery for The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
1010 out of 10 rating
Exceptional
(50 reviews)
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
Trempealeau, WI
8% off
Price is S$3,677
S$3,677
S$525 per night
includes taxes & fees
Image gallery for The Exchange 26 | Historic Bldg, 2 Bed, Dwntwn
9.69.6 out of 10 rating
Exceptional
(10 reviews)
The Exchange 26 | Historic Bldg, 2 Bed, Dwntwn
Winona, MN
8% off
Price is S$2,371
S$2,371
S$339 per night
includes taxes & fees
Image gallery for The Exchange 14 | Historic Bldg, Studio, Dwntwn
9.89.8 out of 10 rating
Exceptional
(6 reviews)
The Exchange 14 | Historic Bldg, Studio, Dwntwn
Winona, MN
8% off
Price is S$1,390
S$1,390
S$199 per night
includes taxes & fees
Image gallery for Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
1010 out of 10 rating
Exceptional
(49 reviews)
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Cochrane, WI
9% off
Price is S$1,661
S$1,661
S$237 per night
includes taxes & fees
Image gallery for The Exchange 11 | Historic Bldg, 1 BR, Dwntwn
9.89.8 out of 10 rating
Exceptional
(7 reviews)
The Exchange 11 | Historic Bldg, 1 BR, Dwntwn
Winona, MN
8% off
Price is S$1,623
S$1,623
S$232 per night
includes taxes & fees
Image gallery for Half a block from the River! Access to private dock coming summer of 2024!
1010 out of 10 rating
Exceptional
(9 reviews)
Half a block from the River! Access to private dock coming summer of 2024!
Buffalo City, WI
13% off
Price is S$1,444
S$1,444
S$206 per night
includes taxes & fees
Image gallery for Fountain City Loft, hot tub, river views
1010 out of 10 rating
Exceptional
(23 reviews)
Fountain City Loft, hot tub, river views
Fountain City, WI
8% off
Price is S$1,985
S$1,985
S$284 per night
includes taxes & fees
Image gallery for Mississippi River View with updated driveway
9.69.6 out of 10 rating
Exceptional
(128 reviews)
Mississippi River View with updated driveway
Minneiska, MN
8% off
Price is S$3,116
S$3,116
S$445 per night
includes taxes & fees
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Find the best place to stay - Sugar Loaf Trailhead
Cabin on the Mississippi River
Sleeps 6 · 1 bedroom · 2 bathrooms
1010 out of 10
Exceptionalexceptional
77 reviews(77 reviews)
Fountain City Loft, hot tub, river views
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Toddy's Cabin
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
Victorian era Mississippi riverview retreat.
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Creekside Cabin Getaway
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!
Sleeps 10 · 3 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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