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.
Apartment in Bayfield
4.81 out of 5 average rating, 255 reviewsOne 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
Cottage in Herbster
4.98 out of 5 average rating, 209 reviewsLake 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
Guest house in Ashland
4.99 out of 5 average rating, 308 reviewsNorrsken 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
Holiday rentals for every style
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Popular amenities for Chequamegon Bay holiday rentals
Other great holiday rentals in Chequamegon Bay
Guest suite in Duluth
4.99 out of 5 average rating, 453 reviewsPrivate Blue Pine Getaway
9–16 Apr
Treehouse in Two Harbors
4.99 out of 5 average rating, 303 reviewsThe ReTreet House
24–31 Jul
Cabin in Ironwood
4.95 out of 5 average rating, 407 reviewsThe Shell Cabin at Rockhound Hideaway
19–26 Jul
Cottage in Herbster
4.99 out of 5 average rating, 137 reviewsApplegate Cottage - South Shore of Lake Superior
10–17 Nov
Tiny home in Lake Nebagamon
4.97 out of 5 average rating, 348 reviewsBerrywood Acres Cabin
13–20 Sep
Yurt in Bayfield
4.94 out of 5 average rating, 399 reviewsTwisting Twig Gardens and Orchard Rustic Yurt
5–12 Oct
Campervan/Motorhome in La Pointe
4.83 out of 5 average rating, 167 reviewsCamp on Main Street
29 May – 5 Jun
Holiday home in Washburn
5.0 out of 5 average rating, 28 reviewsHistoric Hawkes Apartment
14–21 Mar
Apartment in Ashland
4.91 out of 5 average rating, 65 reviewsMain Street apt 2 blocks from Lake Superior!
18–25 Apr
Home in Ashland
5.0 out of 5 average rating, 13 reviewsAdventure Homebase
30 Jan – 6 Feb
Cabin in Bayfield
4.98 out of 5 average rating, 55 reviewsRomantic Vineyard Cabin, Sauna, Plunge Pool
4–11 Nov
Home in Ashland
4.8 out of 5 average rating, 54 reviewsSouth Superior Escape
19–26 Apr
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