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Compare 103 Vacation Homes in Chequamegon Bay with updated reviews, rates, and availability.

Home with a beautiful view of Lake Superior and Madeline Island

10.0 out of 10, Exceptional, (56)
"Communication from MaryAnn was excellent. The home was fully furnished. We did not need anything. Great location. Super clean. Loved our stay there. "
Home with a beautiful view of Lake Superior and Madeline Island

Ontario Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (13)
"Place is very nice and a quick walk to the town, it’s pretty on the outside and was a great place to come back to and grab thing for our hikes or dinner!"
The price is AED 469
AED 733 total
includes taxes & fees
24 Mar - 25 Mar
Ontario Suite @ The Bayfield Guest House

Stately home in Washburn

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay at the Stately Home. It was very comfortable with a lot of space for my family (6 adults). It provided everything we wanted, spacious kitchen, dining room, huge living room & comfortable bedrooms. Visiting in the winter we didn’t have the opportunity to enjoy the deck & backyard, but are looking forward to staying at the Stately for our 2025 holiday getaway. "
Stately home in Washburn

Sunshine House - Historic Bayfield Farmhouse

10.0 out of 10, Exceptional, (11)
"Perfect location for a girls weekend away. The Sunshine House was wonderfully equipped and comfortable for us."
Sunshine House - Historic Bayfield Farmhouse

Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

10.0 out of 10, Exceptional, (35)
"I would absolutely stay here again! It was so beautiful and they have thought of every detail to ALL age groups! The weather was a little gloomy, rainy and cold while we were there but it didn’t matter because we knew we had a safe warm place to come home too! The first night we got there we enjoyed the outdoor area with our kids. We played games and had a little fire going in the fire table! It was much needed family time and we were so blessed to be able to have that at this home! Don’t pass...
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

Lake Shore Home with private dock and large deck--1 mile from Bayfield

10.0 out of 10, Exceptional, (94)
"Great property. "
The price is AED 1,286
AED 2,468 total
includes taxes & fees
1 Apr - 2 Apr
Lake Shore Home with private dock and large deck--1 mile from Bayfield

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

9.4 out of 10, Exceptional, (25)
"Fun place to hang out and sauna with friends after cross country skiing in the area. "
The price is AED 511
AED 1,358 total
includes taxes & fees
25 Mar - 26 Mar
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Superior Suite @ The Bayfield Guest House

9.6 out of 10, Exceptional, (10)
"We stayed for 2 nights and the unit was exactly as listed. The check in was smooth and we had no issues with the unit. Excellent location made walking to and around the downtown area very easy."
The price is AED 525
AED 810 total
includes taxes & fees
24 Mar - 25 Mar
Superior Suite @ The Bayfield Guest House

Huron Suite @ The Bayfield Guest House, Bayfield

9.2 out of 10, Wonderful, (12)
"Very prompt with answering questions. Clean place. "
The price is AED 469
AED 733 total
includes taxes & fees
24 Mar - 25 Mar
Huron Suite @ The Bayfield Guest House, Bayfield

Guest House on Owners Lakefront Property

10.0 out of 10, Exceptional, (81)
"We really enjoyed our stay on Madeline island! The house was great! We enjoyed time on the beach and were glad for the lift up the hill between the beach and the house. The owners were friendly and helpful. The furniture was clean and comfortable. The appliances all worked well. Things to note: bring your own spices/seasonings. Also, the property is about 20 minutes from the ferry landing (some of which is over a well maintained dirt road). We enjoyed the state and county park as well as local...
Guest House on Owners Lakefront Property

At the end of Bark Point lies your perfect vacation home!

9.6 out of 10, Exceptional, (10)
"Beautiful views of Lake Superior.Private, Clean, and well supplied."
At the end of Bark Point lies your perfect vacation home!

Cute cottage on the golf course

9.4 out of 10, Exceptional, (61)
"We have stayed multiple times in this cute cottage. It’s great for us (mom, dad, adult daughter). We especially like how it feels like it’s out in the woods but it’s also walking distance to LaPointe! Also there’s plenty of shade & nice golf course views."
Cute cottage on the golf course

Hemlock Chalet @ Brickyard Creek, Bayfield

9.8 out of 10, Exceptional, (7)
"The property is beautiful and nestled into the trees, which made for a gorgeous winter setting. The bedding and bathrobes are luxurious and comfortable. The soaking tub and the fireplace are incredibly relaxing and ensure for a cozy stay. We enjoyed the quiet holiday weekend reading, doing jigsaw puzzles and sipping hot cocoa by the fireplace. We could have easily stayed cozy in the chalet all week, but we were happy to have access to the beautiful scenery nearby for some exercise. It was a...
Hemlock Chalet @ Brickyard Creek, Bayfield

Peaceful Bayfield Getaway: Lake Superior and Madeline Island Views & Sauna

10.0 out of 10, Exceptional, (3)
"We loved this property for its location and space. We started every morning with coffee on the deck, looking at the beautiful leaves and Lake Superior. The kitchen had everything we needed, with modern appliances and plenty of room for the things we bought. It was great to have so many places to hang out, including a screened in porch, living room and basement. The beds were comfortable and towels were soft. Kevin was very responsive, answering my questions and providing restaurant and hiking...
Peaceful Bayfield Getaway: Lake Superior and Madeline Island Views & Sauna

April/May/June Dates Still Open! Lake Superior Direct Views!

9.8 out of 10, Exceptional, (54)
"We had a great time on the lake, plenty of space for multiple families. Checking in and out was easy."
April/May/June Dates Still Open! Lake Superior Direct Views!

300' of Private Beach

9.0 out of 10, Wonderful, (38)
"Nice beach and property "
300' of Private Beach

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (65)
"We enjoyed our stay and loved the beautiful location and view of the water. It's a very spacious and can accommodate a family. "
Motisi's Sandy Beach

Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!

9.8 out of 10, Exceptional, (44)
"Fantastic view of Lake Superior"
Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!

This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.

10.0 out of 10, Exceptional, (7)
"We enjoyed our time in Herbster. The cabin was stocked with all the creature comforts, and its location - nestled in the woods along the lakeshore - was outstanding. We enjoyed our morning beverages as we watched the sunrise each morning. Cooking breakfast and lunch in the kitchen was easy with all the provided items. For dinner, we ate at The Cranberry Over Superior - and recommend it! We explored Cornucopia and Port Wing, too. The South Shore had plenty to keep us occupied when we ventured...
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.

Beachfront and Lakehouse With All of the Comforts!

10.0 out of 10, Exceptional, (22)
"Host was very responsive and accomodating before and during our visit. Home was clean and as described. Great yard. Relaxing lake. We hope to return next year for more fall colors. "
Beachfront and Lakehouse With All of the Comforts!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chequamegon Bay

Cabin on Lake Superior ~ 11 Mi to Bayfield!

9.8 out of 10, Exceptional, (21)
"Our stay was amazing! Breathtaking views and the cleanliness was top-notch. We'll be back!"
Cabin on Lake Superior ~ 11 Mi to Bayfield!

North Apartment with Lake Superior Views

10.0 out of 10, Exceptional, (29)
"Great property for a short stay!"
The price is AED 551
AED 950 total
includes taxes & fees
13 Apr - 14 Apr
North Apartment with Lake Superior Views

Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!

9.8 out of 10, Exceptional, (44)
"Fantastic view of Lake Superior"
Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.