Chequamegon Bay Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
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Oct 10 - Oct 12

Browse Select Chequamegon Bay Vacation Homes

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Enjoy a peaceful retreat on the balcony with a pergola, seating area, and potted plants.

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
Private Beach and Endless Water
Relax on the sandy shore, where a weathered log and a nearby tree create a serene atmosphere.

Private Beach and Endless Water

8.8 out of 10, Excellent, (42)
"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
Michigan Suite @ The Bayfield Guest House
Stunning views of a serene body of water from a quiet residential neighborhood.

Michigan Suite @ The Bayfield Guest House

9.6 out of 10, Exceptional, (21)
"Clean good bed "
The price is CA $242
CA $364 total
includes taxes & fees
Aug 13 - Aug 14
Michigan Suite @ The Bayfield Guest House
Sunshine House | Historic Bayfield Farmhouse
Relax in a serene outdoor setting with a fire pit, surrounded by lush greenery.

Sunshine House | Historic Bayfield Farmhouse

9.8 out of 10, Exceptional, (13)
"Great place to stay while visiting Bayfield!"
Sunshine House | Historic Bayfield Farmhouse
Beachfront and Lakehouse With All of the Comforts!
Guests can enjoy access to a serene beach with rocks and pebbles along the shoreline.

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 & Spacious Lake Superior Lakefront Cabin on Bark Point
Escape to a secluded forest retreat with a balcony overlooking the treetops.

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
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Situated in a well-maintained yard, this two-story house offers a serene atmosphere.

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

9.4 out of 10, Exceptional, (26)
"This home was wonderful! My family of 6 had more than enough room here and everyone had their own space. There was plenty of towels for us to use. The beds were comfy, we all slept great. We ate dinner one night at Patsy's. Definitely recommend eating there, it was delicious, and we could walk there from the house! The grocery store is also within walking distance. The location was perfect! We spent half our time in Ashland, the other half in Bayfield! Washburn is about halfway between the two....
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Huron Suite @ The Bayfield Guest House, Bayfield
Welcome to The Bayfield Guest House, a traditional two-story building with a distinctive exterior and charming entrance.

Huron Suite @ The Bayfield Guest House, Bayfield

9.4 out of 10, Exceptional, (18)
"We enjoyed soo many great things on our 1st visit to Bayfield! The Guest House was a perfect location to everything"
The price is CA $191
CA $297 total
includes taxes & fees
Sep 11 - Sep 12
Huron Suite @ The Bayfield Guest House, Bayfield
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, (3)
"This house is a great place to stay. We highly recommend!"
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Erie Suite @ The Bayfield Guest House, Bayfield
Relax in this serene bedroom with a large bed, flat-screen TV, and microwave.

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 CA $191
CA $297 total
includes taxes & fees
Sep 1 - Sep 2
Erie Suite @ The Bayfield Guest House, Bayfield
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Modern kitchen with a stainless steel range hood, black stovetop oven, and microwave.

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

8.8 out of 10, Excellent, (5)
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Relax on the pier, taking in the serene views of the water.

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

10.0 out of 10, Exceptional, (20)
"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!
Balsam House in Washburn, Wisconsin
Enjoy a serene beach experience with a clear ocean view, lush greenery, and gentle waves.

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (14)
"Nice home in quiet location. Beds were super comfy, well stocked kitchen. Close to all the dining options in town. "
Balsam House in Washburn, Wisconsin
Spacious home with EV charging station two miles from Big Bay Town Park.
Relax by the rustic fire pit surrounded by a grassy area and natural surroundings.

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

10.0 out of 10, Exceptional, (3)
"We had a great experience. It was a quick driving distance to the big bay town park which makes it very convenient for beach access. Beautiful home with plenty of room for my children to hang out and play. The hosts are very thoughtful and quick to respond. Strongly recommend and will love to come back again. "
Spacious home with EV charging station two miles from Big Bay Town Park.
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Enjoy cooking in this well-equipped kitchen with a central island, oven, microwave, and dishwasher.

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

10.0 out of 10, Exceptional, (52)
"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
Deer Trail Log Home #13 on Lake Delta near Iron River, WI
Interior

Deer Trail Log Home #13 on Lake Delta near Iron River, WI

8.6 out of 10, Excellent, (14)
"This trip started as a snowmobile escape but because of snow conditions, we brought Side x sides. We went exploring and had a nice stay."
Deer Trail Log Home #13 on Lake Delta near Iron River, WI
Luxurious Lake Superior Estate with Outdoor Hot Tub
Escape to a serene forest retreat with a balcony overlooking a tranquil garden and an outdoor area featuring a small waterfall.

Luxurious Lake Superior Estate with Outdoor Hot Tub

10.0 out of 10, Exceptional, (54)
"Loved the property close to everything house was great. I would recommend this place anytime. "
Luxurious Lake Superior Estate with Outdoor Hot Tub
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!
Boats docked at the marina, offering a serene waterfront experience.

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

9.8 out of 10, Exceptional, (76)
"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!
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Enjoy the view from the room's large window with a unique design and central light fixture.

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

10.0 out of 10, Exceptional, (46)
"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.
Motisi's Sandy Beach
Enjoy a peaceful beach experience surrounded by trees and calm waters.

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (69)
"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
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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Top Chequamegon Bay Hotel Reviews

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

10/10 Excellent
"Staff were very kind and helpful. Room was clean and very convenient to get to from the parking lot. Onsite dining was a bonus and delicious! And, of course, amazing view! "
Kelly 2-night trip
Posted 3 days ago
The Washburn Inn - On the Lake