Search Vacation Homes in Chequamegon Bay

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 82 Vacation Homes in Chequamegon Bay with updated reviews, rates, and availability.

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Terrace/patio

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

9.4 out of 10, Exceptional, (24)
"It was a very quaint and cozy place to stay that was very relaxing and enjoyable. "
The price is ￥20,681
￥56,759 total
includes taxes & fees
Jan 5 - Jan 6, 2025
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield
Property grounds

Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield

10.0 out of 10, Exceptional, (3)
"We loved this property for its location and space. We started every morning with coffee on the deck, looking at the beautiful leaves and Lake Superior. The kitchen had everything we needed, with modern appliances and plenty of room for the things we bought. It was great to have so many places to hang out, including a screened in porch, living room and basement. The beds were comfortable and towels were soft. Kevin was very responsive, answering my questions and providing restaurant and hiking...
Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield
Beautiful golf course property with outstanding views and location
Bar (on property)

Beautiful golf course property with outstanding views and location

10.0 out of 10, Exceptional, (71)
"Our family loves Madeline Island and we were looking for a place that was close to everything, yet was quiet and fit all our needs. This place checked all the boxes! This place had everything we needed and more. It was tucked away with a beautiful view of the golf course. It had an ample amount of towels, kitchenware, beds and seating. It was the perfect place to stay. Highly recommend! "
Beautiful golf course property with outstanding views and location
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
Fridge, microwave, oven, stovetop

Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland

10.0 out of 10, Exceptional, (1)
"Our family greatly enjoyed several nights at this cozy cottage! It was clean, had lots of lovely amenities, and was close to Ashland, Washburn and Bayfield. When we had a question, Chelsie responded quickly and thoroughly. Would absolutely recommend it for couples and small families. It didn’t quite provide the lake view we hoped for, but perhaps as leaves fall off, there will be a better view!"
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
Sunset Bay Lodge.
Interior

Sunset Bay Lodge.

9.6 out of 10, Exceptional, (53)
"Beautiful home and property right on lake."
Sunset Bay Lodge.
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (94)
"Great property. "
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Home with a beautiful view of Lake Superior and Madeline Island
Interior

Home with a beautiful view of Lake Superior and Madeline Island

10.0 out of 10, Exceptional, (56)
"Communication from MaryAnn was excellent. The home was fully furnished. We did not need anything. Great location. Super clean. Loved our stay there. "
The price is ￥30,785
￥64,361 total
includes taxes & fees
Jan 3 - Jan 4, 2025
Home with a beautiful view of Lake Superior and Madeline Island
In the Middle Of...
Fridge, microwave, oven, stovetop

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...
Apostle Pines #4 @ Apostle Highlands Golf Course
TV, fireplace

Apostle Pines #4 @ Apostle Highlands Golf Course

9.6 out of 10, Exceptional, (7)
"We have stayed here multiple times. We have family in Bayfield, and we love the golf course. Couldn't be more convenient. This condo has it all! Watching the hummingbirds was a treat!"
The price is ￥32,995
￥72,380 total
includes taxes & fees
Jan 14 - Jan 15, 2025
Apostle Pines #4 @ Apostle Highlands Golf Course
Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!
TV

Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!

9.0 out of 10, Wonderful, (8)
"The real issue was that we were unprepared because the listing was misleading. There were no firepits - listing indicated there were 2. Grill was charcoal and the store on the island charged $20! There were no beach towels - only 4 big towels for showering that needed to double as beach towels. No pizza cutter but decorative seashell butter spreaders - seems odd. No extra paper towels. Listing made it seem that there was a master bathroom - nope. There was one main bathroom and a VERY small...
Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!
Upscale Vacation Stay in Bayfield
Property grounds

Upscale Vacation Stay in Bayfield

10.0 out of 10, Exceptional, (17)
"Very nice "
Upscale Vacation Stay in Bayfield
Suite Four at La Pointe Lodging
Exterior

Suite Four at La Pointe Lodging

10.0 out of 10, Exceptional, (16)
"Great location, walking distance too car ferry and business area."
Suite Four at La Pointe Lodging
Balsam House in Washburn, Wisconsin
Miscellaneous

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (7)
"Very much enjoyed our stay. Clean and comfortable, with outstanding responsiveness and support from the facility manager. Would stay again!"
Balsam House in Washburn, Wisconsin
300' of Private Beach
Beach nearby, sun loungers

300' of Private Beach

9.0 out of 10, Wonderful, (38)
"Nice beach and property "
300' of Private Beach
⭐Lake Superior Waterfront Cabin; Off-season Openings and Summer 2025 Now Open! ⭐
Interior

⭐Lake Superior Waterfront Cabin; Off-season Openings and Summer 2025 Now Open! ⭐

9.8 out of 10, Exceptional, (53)
"We had a wonderful time with our whole family over Thanksgiving. The house was spacious with plenty of room to both spend time together and spread out to get a little space. The host was really responsive and helpful. The house did feel a little bit like a maze to start with but was okay once you got use to it."
⭐Lake Superior Waterfront Cabin; Off-season Openings and Summer 2025 Now Open! ⭐
Hidden Cove Washburn Lake Home
Terrace/patio

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
SUMMER SPECIALS Beautiful lake front, beach and pool table
Exterior

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
Motisi's Sandy Beach
On the beach, sun loungers

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
Lake Superior Beach Haven with Large LakeHouse
On the beach, beach towels

Lake Superior Beach Haven with Large LakeHouse

9.6 out of 10, Exceptional, (14)
"We enjoyed our stay at this VRBO. The description of the home and property was accurate. The grounds and home are well cared for. The property and home were clean. It was a quiet setting. Some games were provided if desired. T.V. was available. The beach area was fun to walk along and explore. We enjoyed a campfire in the campfire ring and wood was provided. The hostess was always responsive to our questions in a very helpful and timely manner. "
Lake Superior Beach Haven with Large LakeHouse
Superior Suite @ The Bayfield Guest House
1 bedroom, desk, free WiFi, bed sheets

Superior Suite @ The Bayfield Guest House

9.6 out of 10, Exceptional, (9)
"Loved our stay in Bayfield! The property was very clean, had all the amenities of a home, and walking distance to a very charming town. I would highly recommend!!!"
The price is ￥25,007
￥37,244 total
includes taxes & fees
Dec 30 - Dec 31
Superior Suite @ The Bayfield Guest House
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.
Don't see what you're looking for?
See all available properties in Chequamegon Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chequamegon Bay

Cabin on Lake Superior ~ 11 Mi to Bayfield!
Fridge, microwave, stovetop, dishwasher

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
Terrace/patio

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
Miscellaneous

North Apartment with Lake Superior Views

10.0 out of 10, Exceptional, (28)
"Cute, well styled apartment with a view of Lake Superior, and a quick trip to downtown. Would stay again!"
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.