Holiday Homes in Chequamegon Bay

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Chequamegon Bay

Erie Suite @ The Bayfield Guest House, Bayfield
1 bedroom, desk, free WiFi, bed sheets

Erie Suite @ The Bayfield Guest House, Bayfield

9.0 out of 10, Wonderful, (14)
" Very nice property, the management was great about making sure we were comfortable and taken care of. And what a view!"
The price is AU$428
includes taxes & fees
11 Aug - 12 Aug
Erie Suite @ The Bayfield Guest House, Bayfield
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
Fridge, microwave, oven, stovetop

This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!

10.0 out of 10, Exceptional, (29)
"We hope to enjoy another stay in the nar future!"
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
Cute cottage on the golf course
Fridge, microwave, oven, stovetop

Cute cottage on the golf course

9.4 out of 10, Exceptional, (64)
"Besides this place needing a few updates and some deep cleaning, it satisfied our need to visit the island and relax. "
Cute cottage on the golf course
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Terrace/patio

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

10.0 out of 10, Exceptional, (2)
"We had an amazing time here. The house is in a great location off the main road with walking distance to everything Bayfield offers. We all enjoyed the house and amenities were top tier."
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Interior

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

10.0 out of 10, Exceptional, (44)
"Loved the location and the convenience of check in. My girls loved the candy machine!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Ontario Suite @ The Bayfield Guest House
Exterior

Ontario Suite @ The Bayfield Guest House

9.2 out of 10, Wonderful, (25)
"Loved the location and property. Everything within walking distance, which is exactly what we wanted. Would definitely stay here again."
The price is AU$432
includes taxes & fees
10 Aug - 11 Aug
Ontario Suite @ The Bayfield Guest House
Michigan Suite @ The Bayfield Guest House
Exterior

Michigan Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (20)
"Needed a place for an overnight for quick run up to Bayfield. The Bayfield Guest house conveniently located near all downtown amenities. "
The price is AU$415
includes taxes & fees
10 Aug - 11 Aug
Michigan Suite @ The Bayfield Guest House
In the Middle Of...
Fridge, microwave, oven, stovetop

In the Middle Of...

9.8 out of 10, Exceptional, (20)
"Nice quiet stay!!"
In the Middle Of...
SandyLand | Sunny Cabin with a Big View
Interior

SandyLand | Sunny Cabin with a Big View

10.0 out of 10, Exceptional, (2)
"wonderful time together, great facility, nearby all the essentials."
SandyLand | Sunny Cabin with a Big View
Beachfront and Lakehouse With All of the Comforts!
On the beach

Beachfront and Lakehouse With All of the Comforts!

10.0 out of 10, Exceptional, (23)
"A great place for families (and their pup). Our kids loved exploring the shoreline after a snowstorm-- they collected ice crystals and loved looking across the bay with the binoculars that were provided. A well stocked kitchen for big meals, this was a great stay! "
Beachfront and Lakehouse With All of the Comforts!
Private Beach and Endless Water
Beach nearby, sun-loungers, beach towels

Private Beach and Endless Water

8.8 out of 10, Excellent, (40)
"Nice beach and property "
Private Beach and Endless Water
Private & Spacious Lake Superior Lakefront Cabin on Bark Point
Exterior

Private & Spacious Lake Superior Lakefront Cabin on Bark Point

10.0 out of 10, Exceptional, (2)
"What a wonderful place to stay! The view and sunsets were incredible. The host was quick to respond. The house was clean and comfy. Great location between Bayfield and Duluth. We stayed there with our two teens and my parents and we all loved it. Would definitely stay again! "
Private & Spacious Lake Superior Lakefront Cabin on Bark Point
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Terrace/patio

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

10.0 out of 10, Exceptional, (36)
"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
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Property grounds

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!

10.0 out of 10, Exceptional, (19)
"As far as a place to disconnect there is not better place! "
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Exterior

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

9.4 out of 10, Exceptional, (23)
"Very comfortable stay. Our family of 7 was in the area to explore the towns and Apostle islands. This location was very centrally located and easy to access."
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Huron Suite @ The Bayfield Guest House, Bayfield
Exterior

Huron Suite @ The Bayfield Guest House, Bayfield

9.4 out of 10, Exceptional, (17)
"We enjoyed soo many great things on our 1st visit to Bayfield! The Guest House was a perfect location to everything"
The price is AU$432
includes taxes & fees
10 Aug - 11 Aug
Huron Suite @ The Bayfield Guest House, Bayfield
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
Smart TV, fireplace, video games, DVD player

Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home

10.0 out of 10, Exceptional, (127)
"This is a beautiful home in a perfect location to enjoy Chequamegon Bay and the surrounding area! The timber frame construction of this home is magnificent, and it is a perfect stay for families and friends. Can't say enough about how much we enjoyed our stay here!"
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (50)
"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!
Marina

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

9.8 out of 10, Exceptional, (75)
"We enjoyed the large space with all the bedrooms. Very close to Big Bay Town Park. "
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!
Luxurious Lake Superior Estate with Outdoor Hot Tub
Exterior

Luxurious Lake Superior Estate with Outdoor Hot Tub

10.0 out of 10, Exceptional, (53)
"Loved the property close to everything house was great. I would recommend this place anytime. "
Luxurious Lake Superior Estate with Outdoor Hot Tub
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
Sign in
Sign up, it's free