Holiday Homes in Chequamegon Bay

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    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 and around

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

10.0 out of 10, Exceptional, (108)
"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!"
Lake Shore Home with private dock and large deck--1 mile from Bayfield

SUMMER SPECIALS Beautiful lake front, beach and pool table

9.8 out of 10, Exceptional, (17)
"We had a great stay. Lots of room, beautiful views, a very clean updated home"
SUMMER SPECIALS Beautiful lake front, beach and pool table

Harbor Hill House Bayfield, WI

2.0 star property
9.0 out of 10, Wonderful, (2)
"The view was awesome!"
Harbor Hill House Bayfield, WI

Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

10.0 out of 10, Exceptional, (54)
"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. "
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!

9.8 out of 10, Exceptional, (79)
"Lori & Craig’s home is a perfect getaway for quiet & relaxation while conveniently located a short drive from Town Park and Big Bay State Park. We traveled with our two kids and their spouses and we had ample space. We all enjoyed the screened in back porch and identifying the different bird calls. Our two dogs loved having the yard to play in. Will definitely be back! "
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!

Private Beach and Endless Water

8.8 out of 10, Excellent, (44)
"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. "
Private Beach and Endless Water

Luxurious Lake Superior Estate with Outdoor Hot Tub

10.0 out of 10, Exceptional, (55)
"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. "
Luxurious Lake Superior Estate with Outdoor Hot Tub

Spacious, secluded sanctuary! Very clean! 5 Queen Beds! Wildlife viewing.

9.8 out of 10, Exceptional, (26)
"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!"
Spacious, secluded sanctuary! Very clean! 5 Queen Beds! Wildlife viewing.

Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

9.0 out of 10, Wonderful, (8)
"We enjoyed every minute of our stay in this comfortable, well-appointed and spotlessly clean house. Highly recommend!"
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

Spacious home with EV charging station two miles from Big Bay Town Park.

10.0 out of 10, Exceptional, (6)
"We had a great time staying at the property! Great amenities and lots of character. Super responsive host when we had trouble checking in!"
Spacious home with EV charging station two miles from Big Bay Town Park.

Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

10.0 out of 10, Exceptional, (5)
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

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

10.0 out of 10, Exceptional, (52)
"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!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (71)
"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! "
Motisi's Sandy Beach

Guest House on Owners Lakefront Property

10.0 out of 10, Exceptional, (86)
"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."
Guest House on Owners Lakefront Property

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

9.6 out of 10, Exceptional, (27)
"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. "
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

Home with a beautiful view of Lake Superior and Madeline Island

10.0 out of 10, Exceptional, (72)
"Pet Friendly a plus! Loved the local fish market right around the corner. The most delicious pumpkin bars from the grocery store in Bayfield"
Home with a beautiful view of Lake Superior and Madeline Island

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

10.0 out of 10, Exceptional, (39)
"This place was very nice, it had everything we needed for a long weekend. "
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home

10.0 out of 10, Exceptional, (129)
"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! "
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home

Orchard Acres | Charming Lake Superior Retreat

Orchard Acres | Charming Lake Superior Retreat

Two bedroom cottage near beautiful Herbster beach.

10.0 out of 10, Exceptional, (91)
"Home is one of the best VRBO properties we have stayed at. It is clean, comfortable and nicely decorated. The location is ideal and private yet within walking distance to the lake and restaurants in town. Owner responds quickly to any questions. Thank you so much for providing a lovely VRBO. This was our 2nd time staying here and we hope to return. "
Two bedroom cottage near beautiful Herbster beach.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chequamegon Bay Hotel Reviews

Find out more about Chequamegon Bay

Find out more about Chequamegon Bay

Chequamegon Bay Holiday Homes information

Number of reviews
942
Accommodation
114 Holiday Homes
Lowest Price
Highest Price