Holiday rentals in Chequamegon Bay

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Top-rated holiday rentals in Chequamegon Bay

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

Superhost

Apartment in Bayfield

4.81 out of 5 average rating, 255 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ, fire pit, and bikes. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. Pool opens in July. $40 pet fee per stay. 🙂 No smoking allowed.

13–20 Dec

€ 131 per night
Guest favourite

Cottage in Herbster

4.98 out of 5 average rating, 209 reviews

Lake Superior's Cranberry River Cottage- The Raven

Enjoy beautiful Lake Superior in the clean cozy modern cottage located in the quaint little town of Herbster where the Cranberry River enters It's just a short couple blocks to the beach and playground. Enjoy the beautiful sunsets, swimming, boating, kayaking, biking, fishing, hunting, and skiing with ATV and snowmobile trails nearby. Explore the Chequamegon Nat'l Forest or venture to Bayfield, home of the Apple Fest, or visit the Apostle Islands Nat'l Lakeshore to see the sea/ice caves.

8–15 Feb

€ 119 per night
Guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 308 reviews

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.

9–16 Mar

€ 178 per night

Popular amenities for Chequamegon Bay holiday rentals

Other great holiday rentals in Chequamegon Bay

Guest favourite

Guest suite in Duluth

4.99 out of 5 average rating, 453 reviews

Private Blue Pine Getaway

9–16 Apr

€ 112 per night
Guest favourite

Treehouse in Two Harbors

4.99 out of 5 average rating, 303 reviews

The ReTreet House

24–31 Jul

€ 130 per night
Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 407 reviews

The Shell Cabin at Rockhound Hideaway

19–26 Jul

€ 109 per night
Guest favourite

Cottage in Herbster

4.99 out of 5 average rating, 137 reviews

Applegate Cottage - South Shore of Lake Superior

10–17 Nov

€ 152 per night
Guest favourite

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 348 reviews

Berrywood Acres Cabin

13–20 Sep

€ 137 per night
Guest favourite

Yurt in Bayfield

4.94 out of 5 average rating, 399 reviews

Twisting Twig Gardens and Orchard Rustic Yurt

5–12 Oct

€ 116 per night
Guest favourite

Campervan/Motorhome in La Pointe

4.83 out of 5 average rating, 167 reviews

Camp on Main Street

29 May – 5 Jun

€ 107 per night
Guest favourite

Holiday home in Washburn

5.0 out of 5 average rating, 28 reviews

Historic Hawkes Apartment

14–21 Mar

€ 142 per night
Superhost

Apartment in Ashland

4.91 out of 5 average rating, 65 reviews

Main Street apt 2 blocks from Lake Superior!

18–25 Apr

€ 131 per night
Guest favourite

Home in Ashland

5.0 out of 5 average rating, 13 reviews

Adventure Homebase

30 Jan – 6 Feb

€ 245 per night
Guest favourite

Cabin in Bayfield

4.98 out of 5 average rating, 55 reviews

Romantic Vineyard Cabin, Sauna, Plunge Pool

4–11 Nov

€ 250 per night
Superhost

Home in Ashland

4.8 out of 5 average rating, 54 reviews

South Superior Escape

19–26 Apr

€ 148 per night

Destinations to explore