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Compare 102 Vacation Homes in Chequamegon Bay with updated reviews, rates, and availability.

Welcome to Twin maple Cottage!
Home with a beautiful view of Lake Superior and Madeline Island
9.8 out of 10, Exceptional, (34)
"My wife, dog, and I had a wonderful stay here. The home is well appointed, very clean, and conveniently located for Bayfield, Washburn, and Madeline Island. Would stay again."
Home with a beautiful view of Lake Superior and Madeline Island
Beach
300' of Private Beach
9.0 out of 10, Wonderful, (28)
"The beach on this property is amazing and cannot be beat! We spent hours enjoying the beautiful view and nice sand. The house is a manufactured home, but it was very clean and comfortable for our family of four. It also has a large yard and two fire pits (one at the beach) to enjoy. The outdoor shower was a fun perk as well. I would definitely book it again."
300' of Private Beach
View of the backyard of our cabin from the Lake.
⭐Large Lake Superior Waterfront Cabin; Limited Summer Availability! ⭐
9.8 out of 10, Exceptional, (43)
"Our stay here was fantastic, just missed mud season which made it even better. Great outdoor lot as well here, roomy backyard for our K9's and frisbee, pretty private, fire at the pit, great lakefront to get down to via a static rope, lots of shoreline got explored! More than enough room inside the place, we only ended up using half of it! Well stocked with dishes, seasonings, towels, blankets, plenty of kitchen utensils (pots/pans/everything) sometimes you don't get this at vrbo's, paper...
⭐Large Lake Superior Waterfront Cabin; Limited Summer Availability! ⭐
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Welcome to South Shore Vista
3 Bears Guest Cottage at South Shore Vista Overlooking Lake Superior
9.6 out of 10, Exceptional, (4)
"A cozy space to get away from everything. Only a 10 minute bike ride from town and the ferry back to Bayfield, this hideaway is an ideal home base to see the area."
3 Bears Guest Cottage at South Shore Vista Overlooking Lake Superior
Reading Nook
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
10.0 out of 10, Exceptional, (17)
"We had such a great time, it was super clean and everything we could ask for and some.! I recommend this home for anyone. Rich was great to work with. We will definitely go back!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Exterior
Two bedroom cottage near beautiful Herbster beach.
10.0 out of 10, Exceptional, (65)
"Third stay! Always amazing! Can’t wait to visit again!"
Two bedroom cottage near beautiful Herbster beach.
Exterior
Cute cottage on the golf course
9.4 out of 10, Exceptional, (56)
"A little tired, but great for our 4 group"
Cute cottage on the golf course
Living Room
Salmo Retreat, House @ Salmo Retreat, Salmo House: Lake Superior Views near Marinas
9.8 out of 10, Exceptional, (33)
"Great views of the lake"
Salmo Retreat, House @ Salmo Retreat, Salmo House: Lake Superior Views near Marinas
Weisel Cabin
Weisel Cabin - Nostalgic Cabin located within walking distance of Downtown La
10.0 out of 10, Exceptional, (9)
"We (my dog and I) thoroughly enjoyed our days at Weidel Cottage. Took walks in the evening to take pictures of the sunset, found the Madeline Museum quite interesting, and enjoyed our morning coffee taking in the view of Lake Superior,"
Weisel Cabin - Nostalgic Cabin located within walking distance of Downtown La
Ashland Vacation Rental | 2BR | 1BA | 751 Sq Ft | Stairs Required
Lake Superior Getaway Near Marina & Beaches!
9.6 out of 10, Exceptional, (4)
"We loved the location, definitely a great part of Ashland and so close to the water."
Lake Superior Getaway Near Marina & Beaches!
Northern Lights 1
#2 Island Overlook, #2 Island Overlook
9.8 out of 10, Exceptional, (7)
"Beautiful scenery, close to many good places to eat and explore. Cabin was exactly as advertised, extremely clean and comfortable."
#2 Island Overlook, #2 Island Overlook
Beach
Beachfront and Lakehouse With All of the Comforts!
10.0 out of 10, Exceptional, (15)
"We enjoyed the quiet location. It was clean, nicely stocked kitchen, fun games, great views. It was so nice to bring our dog with."
Beachfront and Lakehouse With All of the Comforts!
Plants in the living room
The Summer House - basketball court & large yard, perfect for family gatherings
10.0 out of 10, Exceptional, (10)
"Khou and Pao were such gracious and kind hosts. Communication was excellent. Check in and out was easy. My family was gathering for a funeral and it was a beautiful home to gather, both inside and outside. The large kitchen was especially handy. There were plenty of books for kids, which was nice."
The price is AED 1,837
AED 3,057 total
includes taxes & fees
15 Jun - 16 Jun
The Summer House - basketball court & large yard, perfect for family gatherings
Living area
South Superior Escape
9.6 out of 10, Exceptional, (10)
"I have to admit I chose this house because first there were not a lot of choices and secondly there were 8 great reviews. The pictures are accurate but do not capture the charm factor! This house was wonderful! Yes it is an older home but when you walk in you can sense the love and care that has gone into its upkeep. The kitchen was extremely well equipped. The livingroom was spacious and comfy. They even had all of our favorite board games. The upstairs had three spacious bedrooms and an...
The price is AED 477
AED 889 total
includes taxes & fees
26 May - 27 May
South Superior Escape
Welcome to Driftwood Cottage!
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
9.8 out of 10, Exceptional, (38)
"Speechless! Took my mother and two children. The house is gorgeous and very relaxing! The area was great and everything was close by so we were able to do a lot in just a few days!"
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Living area
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
10.0 out of 10, Exceptional, (25)
"Great house and we were very comfortable and it was close enough to the downtown Ashland area so we could walk to the Whistlestop Marathon start and finish. The house was very comfortable and clean and well furnished."
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Exterior
In the Middle Of...
9.8 out of 10, Exceptional, (8)
"The property fit our needs well. The beds we used were comfortable. Plenty of towels and supplies. There were a fair number of Asian beetles, flies and spiders-this is most likely due to being in the woods. There were a few light bulbs out(master bedroom bath and garage door opener light and garage. Nice to have access to a garage as our weather was rainy most days. About 40 minutes to Bayfield and about 20 minutes to Ashland. "
In the Middle Of...
Living Room Open Floor Plan
Blue Spruce Chalet in Brickyard
Blue Spruce Chalet in Brickyard
Living area
Plush & Private Retreat: Wide Vistas of Bayfield and Madeline Island
Plush & Private Retreat: Wide Vistas of Bayfield and Madeline Island
Exterior
Peaceful 3+ Bedroom Home w/ SAUNA, Big Field/firepit, Ravine Garden Patio,
9.6 out of 10, Exceptional, (15)
"This house is comfortable, charming, and clean. The house is friendly. Lots of space. Beautiful woodwork throughout."
Peaceful 3+ Bedroom Home w/ SAUNA, Big Field/firepit, Ravine Garden Patio,
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See all available properties in Chequamegon Bay
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.

Other property types in Chequamegon Bay

Washburn Vacation Rental | 2BR | 2BA | 1,950 Sq Ft | Step-Free Access
Cabin on Lake Superior ~ 11 Mi to Bayfield!
9.6 out of 10, Exceptional, (7)
"Nice house nice setting, easy access to attractions"
Cabin on Lake Superior ~ 11 Mi to Bayfield!
Open concept kitchen/living room with Lake Superior Views
North Apartment with Lake Superior Views
10.0 out of 10, Exceptional, (16)
"Good location for anyone wanting a middle of town walkable get away. We were looking for a little bit of everything, lake views, near food, near shopping, acess to Superior lake walking trail, and this place fulfilled. Nice natural lighting. For being a smaller space it felt large. Basic kitchen tools helped make the kitchen feel practical to use. Loved the bonus coffee!"
The price is AED 551
AED 953 total
includes taxes & fees
29 May - 30 May
North Apartment with Lake Superior Views
Ashland Vacation Rental | 2BR | 1BA | 751 Sq Ft | Stairs Required
Lake Superior Getaway Near Marina & Beaches!
9.6 out of 10, Exceptional, (4)
"We loved the location, definitely a great part of Ashland and so close to the water."
Lake Superior Getaway Near Marina & Beaches!
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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