Vacation rentals in Chequamegon Bay

Find and book unique accommodations on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated vacation rentals in Chequamegon Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Ashland
Norrsken Scandinavian Cottage
The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.
Oct 16 – 23
$160 per night
4.99 out of 5 average rating, 306 reviews
Guest favorite
Cabin in Herbster
SOUTH SHORE A-FRAME//Steps from Lake Superior
A peaceful, feel good place. Newly renovated rustic modern Aframe off Lake Superior's scenic south shore. Surrounded by evergreen and birch trees in an idyllic woodland setting. Enjoy walks to the beach, breathtaking sunsets and beach bonfires, kayaking the famous seacaves, biking, hiking to waterfalls, shopping for vintage treasures or just relaxing/stargazing in the beautiful private backyard. A perfect home base for exploring the Apostle islands, Bayfield and Madeline Island.
Aug 26 – Sep 2
$189 per night
4.94 out of 5 average rating, 133 reviews
Guest favorite
Home in Washburn
Up North Oasis | Groups & Dogs in Bayfield Area
This Up North Oasis is blocks from Lake Superior beaches and 10 miles from Bayfield or Ashland. Gather 'round the kitchen island, share meals in the large dining room, chill out in the spacious living room & handle business in the office space with WiFi. Outdoor front porch with rocking chairs and the fenced-in backyard has beach sand, firepit, and a propane grill on the deck. This house is ready for big groups & the joyful rumpus only dogs & kids can bring to the party.
Sep 16 – 23
$262 per night
4.93 out of 5 average rating, 121 reviews

Popular amenities for Chequamegon Bay vacation rentals

Other great vacation rentals in Chequamegon Bay

Guest favorite
Apartment in Ashland
The Garland City Downtown Apartment
Aug 19 – 26
$140 per night
4.95 out of 5 average rating, 150 reviews
Guest favorite
Cabin in Herbster
Superior Sunsets @ The West Slope (Steam Shower)
Oct 31 – Nov 7
$333 per night
5.0 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Washburn
Palma Lodge
Jan 5 – 12
$135 per night
4.98 out of 5 average rating, 236 reviews
Guest favorite
Treehouse in Bayfield
Boulderridge Treehouse
Mar 19 – 26
$299 per night
4.95 out of 5 average rating, 187 reviews
Superhost
Cottage in Bayfield
Superior Sanctuary: Refined Rustic in the Woods
Sep 24 – Oct 1
$294 per night
4.84 out of 5 average rating, 106 reviews
Guest favorite
Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
Aug 14 – 21
$427 per night
4.99 out of 5 average rating, 140 reviews
Guest favorite
Cabin in Bayfield
The Copper Squirrel of Little Sand Bay Dogs OK
Feb 2 – 9
$206 per night
4.98 out of 5 average rating, 270 reviews
Guest favorite
Tiny home in Saxon
Parker Creek Tiny House
Dec 26 – Jan 2
$113 per night
5.0 out of 5 average rating, 123 reviews
Guest favorite
Home in Ashland
Bungalow (House) on Chequamegon Bay.
May 13 – 20
$125 per night
4.88 out of 5 average rating, 121 reviews
Superhost
Condo in Ashland
Main Street apt 2 blocks from Lake Superior!
Nov 1 – 8
$102 per night
4.9 out of 5 average rating, 63 reviews
Guest favorite
Vacation home in Washburn
Historic Hawkes Apartment
Mar 31 – Apr 7
$99 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Guesthouse in Washburn
Glamping Cabin at Whitecap Kayak Learning Center
Mar 5 – 12
$89 per night
4.89 out of 5 average rating, 9 reviews

Destinations to explore