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Vacation rentals in Madeline Island

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Top-rated vacation rentals in Madeline Island

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Home in Two Harbors

4.85 out of 5 average rating, 320 reviews

Single or multiple nights! Enjoy Fire Pit! #1419

* All are welcome here! * Off street trailer parking! * LOCAL host… Explore Lake Superior * Blocks to Castle Danger Brewery * Fire pit w free firewood! Seasonal Grill Blocks to Lake Superior, Shops & Restaurants. We are nestled between Duluth & Gooseberry Falls A hammock available to use while hiking Work remotely in dedicated office space & fast WIFI..take your lunch break on the shores of the lake Huge yard to play games… grill, or just relax!

Cottage in Two Harbors

4.92 out of 5 average rating, 105 reviews

Fox+FernCottage- Cozy family friendly downtown TH

Fox+Fern Cottage is your cozy home away from home. Our Cottage is walkable to nearly everything in Two Harbors. We are a mile walk to the lake and less than that to Castle Danger Brewery. Fantastic base to explore the North Shore (see reviews). Our yard is a quiet oasis with outdoor seating and swings galore. A/C units installed early JulyRarely will you needwith the cool lake breezes that flow through the shaded house. There's room to pitch a tent on the patio rubber mulch too . Permit #23-05

Treehouse in Iron River

4.92 out of 5 average rating, 61 reviews

Brilliant Fall Colors at Glass Tree House!

Fall graciously into autumn with your 5* stay at The Glass Tree House. Inclusive with all stays, an exclusive, luxury, wine and cheese cruise aboard the Lady Joanne. Take in the brilliant foliage and reflections on the sparkling waters of the Pike Lake Chain. The Glass Tree House truly is a special, private, couples retreat. Luxury amenities include plush robes/slippers and morning Caribou coffee in bed. Enjoy magnificent sunset views and the call of the loons at twilight on your private deck.

Home in Bayfield

5 out of 5 average rating, 13 reviews

Private Spot W/ Madeline Island/Lake Views & Sauna

-Modern, Spacious & Bright w/Great Vibes -Ideal Spot atop Bayfield on 1.56 Acres -Views of Madeline Island & Bayfield -Spacious lower level equally bright & airy -On a dead end street w/Ample parking -TV in each bedroom -Gateway to Apostle Islands -Near Downtown Bayfield & Marina - Wood-burning fireplace -Bonus lounge Room W/ a 65-inch TV, Bean Bags & board games - Fully equipped kitchen - Spacious Primary Bedroom W/ en-suite Bathroom & Deck Access **Special Pricing For Monthly/weekly stays

Chalet in Upson

4.86 out of 5 average rating, 44 reviews

AlpenhausWI Whitecap, Upson WI Waterfalls Hike Ski

Located at Whitecap Mountains Resort, a recreational wonderland! Near Hurley/Ironwood, MI. Easy access to ski hill , lake for fishing, 22 waterfalls within 30 miles. A quiet retreat with lots of windows! New mattresses, linens, updated baths, functional kitchen. Fireplace, outdoor decks, large comfortable space. Duplex with private entry. PLEASE NOTE: Whiteccap Mountains Resort is currently undergoing remodeling and the hotel, pool, hot tub and golf course are not open at this time.

Rental unit in Two Harbors

5 out of 5 average rating, 11 reviews

Lakefront Condo: Pool, Hot Tub, Deck, Fireplaces

Welcome to our Burlington Bay condo, where elegance meets serenity on the shores of Lake Superior. Experience a captivating getaway in our luxurious townhouse. Location: Nestled on the scenic North Shore Waterfront: Lakeside living Amenities: Beach Access, Walking Trail, Deck, Fire Pit, Playground Luxuries: Fireplace, Indoor Pool, Hot Tub, Sauna Extras: 3 TVs, Coin Laundry, Fitness Center Immerse in the tranquility of the lake, relish the breathtaking sunrises and sunsets, & explore nature.

Guest suite in Cornucopia

4.97 out of 5 average rating, 159 reviews

Come love the south shore of Lake Superior

The Cornucopia Sweet Retreat is a unique open concept living space above Corny Coffee in Cornucopia, Wisconsin. We are just steps from Lake Superior and the Cornucopia beach shops. Lost Creek Adventures is across the street and offers guided kayak tours to the sea caves, and Ehlers grocery store has wonderful deli sandwiches and salads. We are located 20 minutes from Bayfield, Wisconsin and the ferry to Madeline Island. The Cornucopia Sweet Retreat is a no smoking / no pet space.

Rental unit in Two Harbors

4.96 out of 5 average rating, 206 reviews

Two Harbors Lodging Apt #5

Enjoy a get-away at this stylish apt located in the heart of downtown Two Harbors. Just a short walk from Agate Bay where you can watch ships come and go. Several eateries are within walking distance, as well as a local brewery. We are close to several state parks for the hiker, or the north shore explorer. Two Harbors also has an excellent golf course. Our Apt's offer you a cozy home-base to come back to after a fun day of exploring the north shore.

Home in Two Harbors

4.97 out of 5 average rating, 317 reviews

Classic Vintage Log Cabin on Lake Superior

Classic, Vintage Log Cabin on 2.5 acres right on Lake Superior - a cozy step back in time! 250 ft. of private bedrock shoreline. 3 Bedrooms: 2 Queen, 1 Dbl. Large updated 3/4 bath, kitchen, and indoor wood burning fireplace. Outdoor firepit, firewood and picnic table. WiFi, TV, and DVD. Close to restaurants, brewery, shops, parks, golf, lighthouse, museums, hiking, biking, skiing, snowmobiling. Send me an inquiry if you can only stay one night.

Cabin in La Pointe

4.86 out of 5 average rating, 232 reviews

7 Pines La Pointe on Madeline Island

NEED ISLAND SERENITY? Instant Book 7 Pines La Pointe on Madeline Island today! Come see how this 2 bedroom/2 bath cabin offers tranquility and peace in one of the more far away desired destinations in all of the country. Beautiful high peaked windows and glass doors, with a very large deck located in a forest of trees on the picturesque/historic Madeline Island, allow guests the feeling of going back in time.

Cabin in Solon Springs

4.9 out of 5 average rating, 41 reviews

Cozy cabin - perfect for you winter getaway!

Nestled deep into the beautiful cabin countryside of Douglas County, you’ll find your escape from the hustle and bustle of every day life when you arrive for your vacation at the Harvest Moon Cabin. This cabin sits deep in the woods on 5 acres of soaring pines. With tons of room to roam and 250’ of sugar sand beach and lakefront, this experience is sure to be one you’ll remember for ages.

Home in Two Harbors

4.84 out of 5 average rating, 61 reviews

Superior View - A Two Harbors Retreat sleeping 10

Come relax at Superior View! This 1896 charmer located in the heart of historic Two Harbors, Minnesota has been completely renovated and tastefully decorated to reflect all the amenities of today with the elegance and charm of yesteryear. Superior View Retreat is a spacious 5-bedroom 2 bath home conveniently located within short walking distance of all that Two Harbors has to offer.

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Popular amenities for Madeline Island vacation rentals

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Other great vacation rentals in Madeline Island

Chalet in Upson

4.8 out of 5 average rating, 20 reviews

Chateau On The Mountain! MM6 Condo at WhiteCap!

Home in Two Harbors

4.88 out of 5 average rating, 90 reviews

Burlington Bay Getaway

Home in Ironwood

4.81 out of 5 average rating, 210 reviews

Cheerful 2 bedroom home away from home

Home in Bayfield

4.94 out of 5 average rating, 18 reviews

Brickyard Lakeside Retreat

Home in Herbster

4.81 out of 5 average rating, 16 reviews

Private Beach Haven with Large Lakehouse

Cabin in Gurney

5 out of 5 average rating, 67 reviews

Potato River Falls Log Cabin Retreat 130 Acres

Home in Ironwood

4.91 out of 5 average rating, 23 reviews

Cheerful 4-bedroom home with a hot tub

Cabin in Mellen

5 out of 5 average rating, 3 reviews

Lakeside - Loon's Nest

Destinations to explore