Condo holiday rentals in Madeline Island

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Popular amenities for Madeline Island condo rentals

Weekly condo rentals

Superhost
Condo in Ironwood Township
4.33 out of 5 average rating, 3 reviews

Lupinedorf #9

PeterRating, 5 stars5 months ago
Overall good experience. Getting in and out was easy. Little bummed that the fireplace didn’t work/was decorative, but otherwise was great. Would rent again.
Condo in Bessemer
4.75 out of 5 average rating, 16 reviews

Room 212 Nature/Hike/Waterfalls/Powdermill Inn

StephRating, 5 stars8 months ago
This was a nice place to spend the night. Plenty of space for everyone. The beds were quite firm, but comfortable and the place was clean and conveniently located within half an hour of a number of gorgeous waterfalls. Suited our purposes nicely!
Guest favourite
Condo in Bayfield
4.92 out of 5 average rating, 26 reviews

Bayfield on the Lake - Waterfront Condo (#303)

PaulaRating, 5 stars2 weeks ago
Great location for watching the boats coming and going, proximity to town and people watching. We could walk everywhere. Hence, our exhaustion after a busy Memorial Weekend.sail boat races could be seen and the spinnaker run was beautiful. Thank you for hosting your lovely home.
Condo in Ironwood
4.88 out of 5 average rating, 41 reviews

Rustic luxury in the NorthWoods III

MichaelRating, 5 stars8 months ago
We came to the Upper Peninsula for fall colors. The location (at the base of a ski hill) was right on the route for one of the best color drives in the area and close to the Copper Peak ski jump that offers rides to the top to see the surrounding countryside. The charging station for our Tesla was super close at the main lodge. Eric's place was super clean, quiet and comfortable. We liked having the pinball machine for some extra fun.
Condo in Ironwood Township
4.73 out of 5 average rating, 11 reviews

Rustic Luxury in the North Woods I

MelindaRating, 5 stars33 months ago
Really wonderful place. So beautifully curated. Just fun, and welcoming. Eric was great at communicating everything. It worked perfectly for our trip through the UP, close to the beautiful Porcupine Mtns and all things Western U.P.
Condo in Bessemer
4.71 out of 5 average rating, 7 reviews

Room 228 Hike/Nature/Waterfalls/Powdermill Inn

JosephRating, 5 stars4 months ago
The place worked well for our visit to the area. Great price compared to other similar lodging. Jay was very responsive to questions and the area is perfect for outdoor recreation.
Condo in Iron River
4.58 out of 5 average rating, 19 reviews

Deer Tail Lodge #10 on Lake Delta

MichaelRating, 5 stars12 months ago
Our stay at the cabin was awesome. Everything about the cabin was great. It was very clean and well stocked. We were definitely in the woods and it was very peaceful. We definitely recommend this place to all who enjoy the serenity away from the rat race.
Condo in Iron River
4.67 out of 5 average rating, 21 reviews

Deer Trail Resort Lakeside 5 on Lake Delta

NaomiRating, 5 stars22 months ago
We had an excellent time here! It's very close to the lake and has a fire pit. The hot water ran out fairly quickly, but the cabin and amenities were well worth the price. The hosts were also extremely communicative which was appreciated!

Pet-friendly condo rentals

Superhost
Condo in Ironwood Township
5 out of 5 average rating, 4 reviews

Summertime Bliss at Powderhorn Mountain

SebastianRating, 5 stars3 months ago
This is our second time with Your North Vacation and it felt like at home, once again. The place was spotless and cozy. We loved the location right in front of Big Powderhorn and 15 min away of Snowriver. They had stuff for our dog and some other details that we loved! Would not stop recommending Your North Vacation for your vacations in the UP! Host was super responsive as I had some issues with my email during our check-in.
Superhost
Condo in Bessemer
4.81 out of 5 average rating, 47 reviews

Sky Top Summer Retreat at Powderhorn Mountain

BayleeRating, 5 stars3 months ago
Had a great time here! The unit was super clean and great location next to big powderhorn. The unit was super spacious that was perfect for 2 people and our 2 pups, but could easily accommodate 4 people. The coffee and tea supply was a nice touch😇 My only complaint would be unclear check in instructions. I didn’t receive the email and even that had missing unit numbers, so I wasn’t sure which door was ours. The host was responsive so everything was settled quickly. Would definitely stay here again!
Condo in Bessemer
4.65 out of 5 average rating, 57 reviews

Room 120 - Ski/Nature/Sled/Powdermill Inn

KariRating, 5 stars3 weeks ago
Great spot to stay at! Perfect home base for exploring the UP in the summer.
Condo in Bessemer
4.71 out of 5 average rating, 42 reviews

Powdermill Inn, outdoor enthusiasts!

ChrissyRating, 5 stars3 months ago
Great location from ski lodge. Nice place for the money. Only downside is not being able to control the heat. Otherwise, we loved it and will be back. Took our dogs so that was a huge bonus for us.
Top Guest favourite
Condo in Ironwood
4.95 out of 5 average rating, 108 reviews

Downtown "Yellow Room" at Villages on Aurora

AliciaRating, 5 stars3 months ago
Very cute and clean place. Had everything we needed to feel at home including a laundry room where we could wash our kids muddy clothes after playing outside all day. Would recommend!
Superhost
Condo in Bayfield
4.7 out of 5 average rating, 33 reviews

Boatworks #201. Sleeps 8. Pet Friendly. Elevator

DebbieRating, 5 stars7 months ago
Tania’s home was as described. It is a great location, spacious, clean, and had comfortable beds. The kitchen is well stocked and in great condition. We were able to walk to everything and the balcony has a lovely view. We’d definitely recommend this condo!
Guest favourite
Condo in Ironwood
4.97 out of 5 average rating, 93 reviews

Downtown "Blue Room" at Villages on Aurora

MattRating, 5 stars5 months ago
Very clean. It was in a great location just two minutes away from where our family lives. Definitely plan on having this be our go to whenever we visit Ironwood.
Guest favourite
Condo in Ironwood
4.95 out of 5 average rating, 113 reviews

Downtown "Red Room" at Villages on Aurora

BenjaminRating, 5 stars2 months ago
We had a great experience at North Vacation Rentals. The host was helpful and responsive. Apartment was clean and well stocked. This is our second time staying here and would recommend to anyone when visiting Ironwood.

Condo rentals with a pool

Condo in Two Harbors
New place to stay

Sunrise Suite on Lake Superior | Pool & Hot Tub

SamuelRating, 5 stars3 weeks ago
Clean and quiet with a nice view. End unit a plus.
Superhost
Condo in Bayfield
4.8 out of 5 average rating, 361 reviews

One Minute Walk to Lake Superior. Brookside #11

SharonRating, 5 stars2 weeks ago
Comfortable, clean second floor condo a short drive from Bayfield with wooded view from kitchen window. Working jacuzzi and adequate cooking supplies. Jon was quick to respond to questions.
Guest favourite
Condo in Two Harbors
5 out of 5 average rating, 5 reviews

Water's Edge! Direct lake access, Newly remodeled

GarnetRating, 5 stars3 days ago
Words can’t even express the amount of gratitude we had for this space. We absolutely took advantage of the entire place. It was magical!. The location, the food, the view, all the people and all intentional things, What a gift!. Thanks for sharing your beautiful place with us. We will be back.
Condo in Upson
4.9 out of 5 average rating, 20 reviews

Whitecap Mountain: Mountain Meadows #4 Nitecap

JennyRating, 5 stars33 months ago
We had a wonderful time at Gary’s place! We spent the weekend riding atv and this condo has amazing location to get to the trails with lots of extra parking close by. Gary’s place had lots of space with a great view of the lake! Very nice condo!
Guest favourite
Condo in Bayfield
4.79 out of 5 average rating, 159 reviews

One Minute Walk to Lake Superior. Brookside #10

JenniferRating, 5 stars3 weeks ago
It was a perfect place for a get-a-away! Clean and comfortable and the option of kitchenware was sufficient for some basic cooking. I would definitely recommend for a single person or a couple, maybe not for a family with multiple children; everything is so close together it would be hard to not wake up the kids or vs-versa.
Superhost
Condo in Two Harbors
New place to stay

Waterfront Two Harbors Retreat -Pool/Hot Tub (2BR)

KeithRating, 5 stars1 month ago
Really enjoyed it! Well run and everything seems brand new. Will return. Thank you!
Guest favourite
Condo in Two Harbors
4.83 out of 5 average rating, 6 reviews

Sunset Suite on Lake Superior | Pool & Hot Tub

RandyRating, 5 stars3 days ago
Rochelle and I really enjoyed the unit and the property and found it to be a great home base for a North Shore visit.
Condo in Two Harbors
5 out of 5 average rating, 3 reviews

Penthouse w/pool & hot tub

LindsayRating, 5 stars1 week ago
This spot is a gem! We spent a beautiful weekend here with my family- and my kids are already asking when we can go back. Amazing views, lots of privacy in this beautiful and comfortable condo. We could have spent all weekend in the very fun pool and wandering the shores of Lake Superior. The location is also amazing jumping off point for exploring. Don’t miss Cedar Coffee in Two Harbors. We also went north to check out split rock and the black beach and south to the new scenic cafe, Duluth grill, and summer adventures and spirit mountain. The condo has three suites which offer nice space for each member of your party. Perfect for our family of five, and would also be great for a few families or a girls trip. The spot was easy to access and Karen was really responsive. I cannot wait to go back!

Destinations to explore