Holiday Homes in Chequamegon Bay

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Featured Holiday Homes in Chequamegon Bay

"The home and location were perfect for our friends weekend! Views of Lake Superior are seen from every room. We enjoyed the comfortable beds and appreciated the host’s attention to detail. Monica was very easy to communicate with and would love to return for another stay!"

"We had a great stay. Lots of room, beautiful views, a very clean updated home"

"The view was awesome!"

"Had a great weekend stay, the house was very clean and well kept. The owners have done an excellent job fixing it up. The owners do a great job with communication as well. I'd highly recommend staying here. "

"We loved our stay at Lori and Craig’s home in the woods. The house is wonderful and felt like a home from the moment we entered. There was plenty of space for the five of us. The house was sparkling clean and had everything we needed. The beds were super comfortable, the towels plush and cozy. We loved watching and listening to birds on the screened-in porch and eating breakfast and playing games on the big table. Unfortunately, our stay was short but we are hoping to return one day….."

Beach nearby, sun-loungers, beach towels

"Very little traffic and very quiet beach. It was early in the year before tourist season but very quiet neighborhood. Would definitely stay here again. House was very clean. "

"This estate is by far one of our favorite finds. Tucked away and private views of Lake Superior that are breathtaking. Grounds meticulously cared for and designed that makes you feel like you are walking in a magical paradise from a movie or a dream. Thank you for sharing your lovely home. We hope to come back soon and bring more family to share this beautiful piece of Heaven on Earth. "

"The house was great and the area is amazing. Very quiet and peaceful with tons of wildlife. Saw so many deer - definitely keep your eyes open and follow the posted speed limit!"

"We enjoyed every minute of our stay in this comfortable, well-appointed and spotlessly clean house. Highly recommend!"

includes taxes & fees

28 Sept - 29 Sept

"We had a great time staying at the property! Great amenities and lots of character. Super responsive host when we had trouble checking in!"

"The stay was great, and the hosts were exceptionally accommodating. It worked very well for the two of us and a dog, and the unit could certainly entertain more. The hosts go above and beyond on the housewarming touches and helpfulness via messaging communications. Would recommend!"

"Sweet cottage in a great location with the best shoreline. The rooms were comfortable with all essentials included and easy check in and check out. The beach provided so much fun for our family and the kids even enjoyed swimming in May! "

"The seclusion of the property and the private beach were incredible. The privacy, waterfront, and island views made this a great choice for our family vacation."

"Myself and my family stayed here for a family vacation. Home was very clean in a quiet neighborhood that was nearby a few nice restaurants and cafés. Owner was communicative and a pleasure to work with. "

"Pet Friendly a plus! Loved the local fish market right around the corner. The most delicious pumpkin bars from the grocery store in Bayfield"

"This place was very nice, it had everything we needed for a long weekend. "

Smart TV, fireplace, video games, DVD player

"This was our 2nd stay at this property. We were able to enjoy the beach and the beautiful deck. The property is very well stocked with everything we needed! We all loved the outdoor shower…even the 4 year old boys were excited to shower! We hope to be back again! "