Holiday rentals in Red Wing

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Top-rated holiday rentals in Red Wing

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A view of the property surrounded by trees, featuring a red barn-style building and a spacious green area. The sky is partially cloudy, and a white dome structure is visible nearby. Lush foliage frames the scene, enhancing the natural landscape.
Guest suite in Red Wing
5 out of 5 average rating, 136 reviews

Adventure Time

The Guest Suite is on the lower level of the home. Perfect for overnight, weekend, and short-term guests in mind. Surrounded by Frontenac State Park, enjoy the quiet or head out for an adventure. A clean open space with all amenities needed for a comfortable stay. The home is a quick drive to either Red Wing or Lake City all though I live in country on gravel road . It's a scenic 45-minute drive to Rochester. Head down the road and enjoy Lake Pepin. Bring your water toys and enjoy the day

Guest favourite
An aerial view showcases a rural property featuring multiple buildings, including a large red barn, a farmhouse, and a smaller structure. Lush greenery surrounds the area, with trees and an open field visible. Pathways connect the buildings, creating an inviting outdoor space.
Farm stay in Cottage Grove
4.95 out of 5 average rating, 557 reviews

Luxury Barn Cottage and Villa at Hope Glen Farm

The Corn Crib Cottage Barn or Villa is a luxurious and rustic 1100 square foot space. The Corn Crib originally used to dry corn and animal housing. This is a very rare historical building built in the 1920's The villa has a 2 person whirlpool jacuzzi , rain shower, beautiful full kitchen, fireplace and next to the 550 acre Washington County Cottage Grove Ravine regional park reserve. The Cottage is near the famous lofty lodge treehouse in the area. Treehouse on airbnb listing number 14059804

Top guest favourite
A decorative sign featuring a stylized horse silhouette, marked with 'Lucky Day Farm' and 'EST 2020,' stands atop a snow-covered wooden base. The sign contrasts against a backdrop of a blue building, enveloped in a layer of fresh snow.
Guest house in Cannon Falls
4.98 out of 5 average rating, 312 reviews

Cannon Valley Lucky Day Farm - Farmhouse Loft

A beautiful farmhouse loft just minutes from Cannon Falls / Red Wing and located directly on the Cannon Valley Bike Trail. * Canoe, kayak or tube the Cannon River at Welch Mill -5 mi * Bicycle the 19.2-mile paved Cannon Valley Trail, trail crosses the property * Treasure Island Resort & Casino -11 mi * Hike Barn Bluff in Red Wing -13 mi * Golf at area courses * Wineries & breweries -4 mi * Drive the scenic Great River Road * Birdwatch eagles * MOA and Twin Cit * Ski at Welch Village -6 mi

Top guest favourite
A wooden sauna is positioned in the center of a rustic room with exposed beams and corrugated metal walls. Two wooden rocking chairs sit nearby. Light enters through several windows, and a basket is placed on the floor, enhancing the inviting, serene environment.
Home in Stockholm
4.96 out of 5 average rating, 270 reviews

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at quiet Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. This vintage home farmstead on 4 acres, was built in the mid 1850s and has old world character architecture with the comforts of modern day amenities. The southern exposure enclosed front porch is the favorite gathering spot for most everyone that has stayed in the home. This 2 bedroom 1 1/2 bath property has potential for sleeping up to 8 guests.

Superhost
A glass house reflects natural surroundings, enclosed by trees and sunlight. The interior features a spacious bed draped in white linens, with cozy seating visible nearby. A wooden deck extends outwards, complemented by outdoor furniture and decorative lanterns.
Dome in Afton
4.86 out of 5 average rating, 385 reviews

Star Gazing Glass House 4 Season with Hot Tub

This glass house has a mini split offering both heat and air conditioning. There is something truly magical about being submersed in nature. Watching beautiful snowflakes cascade around its walls, snuggled under heated blankets while star gazing. Rainstorms have a new meaning, sunsets and sunrises become a life-changing experience. This is a photographer's dream, a romantic getaway, or the perfect place to reconnect with yourself. Private hot tub and fire pit.

Top guest favourite
A spacious living area features a sectional sofa and two cozy armchairs, arranged on a light-colored rug. Natural light enters through large windows, illuminating the modern kitchen visible in the background, which includes sleek cabinetry and contemporary appliances.
Home in Red Wing
4.97 out of 5 average rating, 77 reviews

Quiet Rural Escape Updated Home 2 Acres Fire Pit

About 4 miles from downtown Red Wing. Short drive to wineries, brewery, golfing, the bluffs, and Mississippi River! Perfect for a relaxing getaway or an adventure-filled retreat, this charming property offers all the comforts of home and more. Enjoy our newly renovated home, you will have access to 2 bedrooms, 1 full bath, dining, living room, fully stocked kitchen. Situated on 2 acres. State land for hiking near by.

Guest favourite
A living room is presented with two leather chairs and a gray sofa along a striped area rug. A small table with a lamp is positioned beside a plant. Light enters through large windows dressed with flowing curtains.
Home in Red Wing
4.92 out of 5 average rating, 166 reviews

Charming 3 BR Cottage Home in Historic Red Wing.

L'EPI De BLE is located in the West Residential Historic District of Red Wing. This 3 bedroom 1.5 bath cottage was built in the late 1800's and has been well-maintained and tastefully updated with a fully renovated kitchen and bathrooms to meet the modern comforts of today's lifestyle. The home is has it all whether it's for family weekend away, working remote, or looking for an extended stay.

Top guest favourite
A modern cottage sits on a lush green lawn near a sunset backdrop. The silhouette of the structure is visible with expansive windows reflecting the warm colors of the sky. Outdoor seating arrangements made of wood provide a welcoming space for relaxation.
Home in Maiden Rock
4.95 out of 5 average rating, 162 reviews

Lake Pepin Cottage on the Bluff

Bluff Cottage Overlooking Lake Pepin Compact and beautiful, this modern cottage is situated on 8 acres on a bluff overlooking Lake Pepin in the driftless area of Wisconsin. The house is mostly windows, with spectacular views of the sunrise, the sunset, Lake Pepin and the Milky Way. House has all the amenities, and sleeps four, plus a wood-burning sauna.

Top guest favourite
Cabin in Pepin
4.98 out of 5 average rating, 118 reviews

New Hot Tub Nov 2025, Firepit, Eco-Friendly

The Paige is an updated 102 yr old cabin is family-friendly and dog-friendly. It is near all the great amenities in Pepin including Villa Belleza (only 0.5 mile away), The Homemade Cafe (one block away), Harbor View Cafe, The Pickle Factory, Lake Pepin, and Stockholm, WI. A great central location for all Lake Pepin area activities!

Top guest favourite
The spacious living room features a comfortable couch and a large Smart TV positioned beside a window air conditioning unit. Multiple windows enhance natural light, while a round rug adds warmth. Decorative elements, such as wall art and a lamp, contribute to a cozy atmosphere.
Flat in Red Wing
4.8 out of 5 average rating, 433 reviews

Pet-friendly downtown apt

Cozy and comfortable 1-bedroom apartment on the first floor of a triplex blocks from downtown Red Wing. Apartment is within walking distance to the riverfront and Main Street and in close proximity to Memorial Park & Barn Bluff Trailhead. **Listing price includes a 3% City of Red Wing lodging tax.

Guest favourite
A modern kitchen area is visible, featuring white cabinetry and a sleek countertop. A microwave sits above a coffee maker. The warm wooden floor extends into a connecting hallway, complemented by decorative wall pieces and ambient lighting. The ceiling showcases exposed ductwork for an industrial touch.
Loft in Prescott
4.98 out of 5 average rating, 344 reviews

Historic Loft- Top spot in Prescott

Bean Loft is located in a charming 1870's building on Main Street in downtown Prescott. Steps from restaurants, pubs, antique stores and a boat marina. There is plenty of sleeping room for groups, an office, large living room and full kitchen outfitted with everything to prepare and serve a meal.

Top guest favourite
A single-story home is set against a clear blue sky, showcasing a red exterior with white trim. A wooden ramp leads to the entrance, and patches of snow remain in the yard. Trees line the background, highlighting the natural surroundings.
Home in Hager City
4.97 out of 5 average rating, 204 reviews

Quiet,peaceful, by Trimbelle River. No Internet.

Peaceful, beautiful property with Trimbelle River within walking distance. Close to Red Wing /Twin Cities, Stockholm/Pepin, restaurants, bars and Treasure Island Casino. Different kinds of wildlife. Nice road to walk or bike. I've been here long time and enjoy it all still.

Popular amenities for Red Wing holiday rentals

When is the best time to visit Red Wing?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Red Wing?

    Yes! Work meets play with ease at over 20 vacation rentals in Red Wing featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Red Wing?

    Four-legged friends are welcome in Red Wing. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Red Wing?

    Red Wing has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Red Wing?

    Experience the best of Red Wing with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Red Wing have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Red Wing. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Red Wing have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Red Wing. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Red Wing

  • Total holiday rentals

    Explore 50 holiday rentals in Red Wing

  • Nightly prices starting at

    Red Wing holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 3,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Red Wing holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Red Wing rentals

  • 4.9 Average rating

    Red Wing stays are highly rated by guests – averaging 4.9 out of 5!

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