Search Vacation Homes in Chequamegon Bay

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Compare 106 Vacation Homes in Chequamegon Bay with updated reviews, rates, and availability.

300' of Private Beach
9.0 out of 10, Wonderful, (37)
"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
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
9.8 out of 10, Exceptional, (47)
"We loved the decor and the beds and furniture were super comfortable!"
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
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.
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
9.2 out of 10, Wonderful, (22)
"We stayed for a family weekend with our adult son. Loved the proximity to hiking trails and restaurants & brewery in Washburn. The place isn't fancy, but was perfect for us. We enjoyed the sauna and campfires outside."
The price is SAR 695
SAR 1,603 total
includes taxes & fees
27 Nov - 28 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
SUMMER SPECIALS Beautiful lake front, beach and pool table
9.8 out of 10, Exceptional, (15)
"We had a great time staying at this location. The fall weather was nice and cool and the scenery was beautiful. The house was very nice and clean with lots of rooms and things to do. Would reccommend!"
SUMMER SPECIALS Beautiful lake front, beach and pool table
Lake Shore Home with private dock and large deck--1 mile from Bayfield
10.0 out of 10, Exceptional, (93)
"Monica has a beautiful home right on Lake Superior. There was everything we needed to make family meals. The beds were very comfy,and the home was immaculate. Would highly recommend this property!"
Lake Shore Home with private dock and large deck--1 mile from Bayfield
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
10.0 out of 10, Exceptional, (6)
"Beautiful property in a quiet area with a 35 minute easy drive to Bayfield. Near Myers’s Beach which has an absolutely stunning bluff hike. "
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
10.0 out of 10, Exceptional, (22)
"We had a fantastic time at the Lenawee Getaway! The backyard games and fire pit were so fun for our family and had a blast playing the games. This was the getaway our family needed. We had fun exploring Herbster and the fun shops/establishments in town! Great food and very friendly people! Thank you!"
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
Still Life Cottage @ Brickyard Creek, Still Life Cottage @ Brickyard
9.2 out of 10, Wonderful, (10)
"We enjoyed the art-filled cabin. It was very clean and comfortable. Beautiful area too! "
Still Life Cottage @ Brickyard Creek, Still Life Cottage @ Brickyard
Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!
10.0 out of 10, Exceptional, (19)
"Well maintained property with several amenities. We had a great time with our family & dog. "
Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!
9.8 out of 10, Exceptional, (42)
"Loved everything about this place! We had a great time and we will be back! "
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
10.0 out of 10, Exceptional, (121)
"The pictures don’t do this place justice! We had an amazing time with friends and family. Our hosts were unbelievably communicative - and they made our stay as easy and comfortable as could be. Halfway through the trip, our party discussed making this an annual rental! 5 stars!"
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
In the Middle Of...
9.8 out of 10, Exceptional, (18)
"The house and the property were very clean and nicely kept. The views were great, wildlife everywhere! We really enjoyed the amount of bedrooms and space. We didnt have a single complaint! Very nice!"
In the Middle Of...
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the
10.0 out of 10, Exceptional, (18)
"Watch sunrise each day, follow critter tracks on the beach, breathe in the pine aroma and relax. Top tip: the electric heater has a remote—no one has to get out of bed to turn it on in the morning! Neat and tidy with the essentials. We loved it."
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the
MadPad - Unique Family Home located right on the Golf Course!
8.8 out of 10, Excellent, (3)
"Great weather, nice home, great week Thank you"
MadPad - Unique Family Home located right on the Golf Course!
Suite One at La Pointe Lodging
10.0 out of 10, Exceptional, (12)
"Not for publication, but it would be great to have mugs for coffee. The teacups that are part of the pottery set are prettty pathetic. Otherwise, a lovely place. "
Suite One at La Pointe Lodging
White Pine Chalet @ Brickyard Creek, Modern Hygge Chalet In The Woods
10.0 out of 10, Exceptional, (8)
"Tucked away among trees, there was ample opportunity to hike in wooded trails. Not too far from Bayfield itself, and close to Frog Bay Tribal Park as well. Especially appreciated the large screened porch in the back!"
White Pine Chalet @ Brickyard Creek, Modern Hygge Chalet In The Woods
Hemlock Chalet @ Brickyard Creek
9.8 out of 10, Exceptional, (6)
"Absolutely beautiful property! So peaceful, comfortable and gorgeous!"
Hemlock Chalet @ Brickyard Creek
Island Fox - Home nestled in the Woods with Screened-in Porch!
10.0 out of 10, Exceptional, (5)
"Island Fox was a nice home to stay on the island and had everything we needed and was conveniently located. The screened in porch was comfortable to sit and read without the bugs. We even saw a bear! The check in process ended up being very easy however I didn’t get communication on it in advance and no response when I messaged and called on our drive up. All in all a great stay. Thank you for sharing your home."
Island Fox - Home nestled in the Woods with Screened-in Porch!
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!
Hidden Cove Washburn Lake Home
10.0 out of 10, Exceptional, (38)
"The pictures do not do this home justice. It has great views and beautiful grounds!"
Hidden Cove Washburn Lake Home
North Apartment with Lake Superior Views
10.0 out of 10, Exceptional, (27)
"Cute, well styled apartment with a view of Lake Superior, and a quick trip to downtown. Would stay again!"
The price is SAR 470
SAR 857 total
includes taxes & fees
8 Dec - 9 Dec
North Apartment with Lake Superior Views
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.