Search Vacation Homes in Chequamegon Bay

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Compare 103 Vacation Homes in Chequamegon Bay with updated reviews, rates, and availability.

Home with a beautiful view of Lake Superior and Madeline Island

10.0 out of 10, Exceptional, (57)
"Loved the property and view!"
Home with a beautiful view of Lake Superior and Madeline Island

Michigan Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (16)
"The Michigan Room was perfect! It had everything we needed and was walking distance to shops and restaurants! Will definitely stay again!"
The price is SAR 520
SAR 800 total
includes taxes & fees
4 Jun - 5 Jun
Michigan Suite @ The Bayfield Guest House

Ontario Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (13)
"Very clean, comfortable, and close to downtown area."
The price is SAR 520
SAR 804 total
includes taxes & fees
12 May - 13 May
Ontario Suite @ The Bayfield Guest House

Stately home in Washburn

9.8 out of 10, Exceptional, (19)
"We loved our stay! The house was bigger than we thought and the fenced-in backyard was amazing! We would definitely stay there again :)"
Stately home in Washburn

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

9.4 out of 10, Exceptional, (26)
"It was a very quaint and cozy place to stay that was very relaxing and enjoyable. "
The price is SAR 866
SAR 1,823 total
includes taxes & fees
26 May - 27 May
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!

9.8 out of 10, Exceptional, (44)
"Fantastic view of Lake Superior"
Washburn Beach House. Private Beach, 11.6 Miles from Bayfield!

Sunshine House - Historic Bayfield Farmhouse

10.0 out of 10, Exceptional, (11)
"Great place to stay while visiting Bayfield!"
Sunshine House - Historic Bayfield Farmhouse

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

10.0 out of 10, Exceptional, (35)
"We had a great stay, we will be back next time we are in the area!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

Beachfront and Lakehouse With All of the Comforts!

10.0 out of 10, Exceptional, (23)
"We had beautiful fall days to enjoy this private spot. It’s so quiet you can hear the owls hooting while you’re admiring the night skies. "
Beachfront and Lakehouse With All of the Comforts!

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!

A Cozy Getaway in Ashland

10.0 out of 10, Exceptional, (1)
"The house was clean, had everything we needed and was the perfect home away from home for my husband and I and our 2 kids. Will definitely stay again when we make a trip to Ashland!"
A Cozy Getaway in Ashland

At the end of Bark Point lies your perfect vacation home!

9.6 out of 10, Exceptional, (10)
"We had a wonderful stay here. Very peaceful remote location. We loved relaxing on the porch enjoying the lake breezes."
At the end of Bark Point lies your perfect vacation home!

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

Cute cottage on the golf course

9.4 out of 10, Exceptional, (61)
"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

Hemlock Chalet @ Brickyard Creek, Bayfield

9.8 out of 10, Exceptional, (7)
"Clean and the bed was very comfortable"
Hemlock Chalet @ Brickyard Creek, Bayfield

Peaceful and Elegant Home: Lake Superior and Madeline Island Views & Sauna

10.0 out of 10, Exceptional, (3)
"Nice accommodations - had everything my family needed. Loved the large dining room table that allowed my family to eat and play games together. Kevin (the host) was very quick to respond to any questions."
Peaceful and Elegant Home: Lake Superior and Madeline Island Views & Sauna

300' of Private Beach

9.0 out of 10, Wonderful, (38)
"Nice beach and property "
300' of Private Beach

3 Last Minute May Weekend Openings, Lake Superior Panoramic Views!

9.8 out of 10, Exceptional, (55)
"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."
3 Last Minute May Weekend Openings, Lake Superior Panoramic Views!

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (65)
"Right on the beach with nice porch. Great place, exactly what we wanted for our weekend stay!"
Motisi's Sandy Beach

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

10.0 out of 10, Exceptional, (95)
"Great property. "
Lake Shore Home with private dock and large deck--1 mile from Bayfield
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

Mission Springs Resort

3.0 star property
9.4 out of 10, Exceptional, (54)
"We had a great time. It was perfect for us and our 2 older kids. Breathtaking view of Lake Superior. Great communication with host. Highly recommend."
The price is SAR 492
SAR 618 total
includes taxes & fees
8 May - 9 May
Mission Springs Resort

Hidden Cove Washburn Lake Home. Sleeps 6.

10.0 out of 10, Exceptional, (40)
"Great place to stay, was very clean and neat when we arrived. Check in was easy. "
Hidden Cove Washburn Lake Home. Sleeps 6.

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!
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.