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Vacation rentals in Lakeside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lakeside

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

Guest favorite

Home in Port Wing

4.9 out of 5 average rating, 177 reviews

Kinney Valley Farm

This rustic, but modernized farmhouse is on 110 acres of woods and apple orchards. Snow is great now! Cross country ski trails are " skier-groomed" on our property. Multiple areas for groomed skiing are within 30-45 minute drives. Located just 3 miles from the south shore of Lake Superior, and 30 minutes from the Apostle Island Sea Caves, spectacular now with winter ice sculptures, Kinney Valley Farm is a cozy place to stay, while exploring the pastoral winter beauty of Northern Wisconsin.

May 14 – 21

G$23,895 GYD per night
Guest favorite

Guest suite in Superior

4.97 out of 5 average rating, 655 reviews

Penrose House Suite for 4 (Lic. No. TBES-AVZSAR)

Penrose house is an original Edwardian home having a private and separate third floor suite. Guest access and entry to the suite is through two high security doors leading to a back stairway used exclusively by guests. Safe off-street parking is available at the rear of the property for guest use only. Our property is located in one of the most sought after streets in the heart of the Central Park area of Superior, Wisconsin. We are centrally located for tourist destinations in the Northland.

Feb 18 – 25

G$18,150 GYD per night
Guest favorite

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.

Feb 8 – 15

G$25,388 GYD per night

Popular amenities for Lakeside vacation rentals

Other great vacation rentals in Lakeside

Guest favorite

Guest suite in Brule

4.97 out of 5 average rating, 135 reviews

The Bee's Balm

Aug 31 – Sep 7

G$21,886 GYD per night
Guest favorite

Cottage in Lake Nebagamon

5.0 out of 5 average rating, 124 reviews

Guest House at the Lake

May 18 – 25

G$32,532 GYD per night
Guest favorite

Apartment in Hermantown

4.79 out of 5 average rating, 652 reviews

Beautiful, private vacation space

Nov 23 – 30

G$21,419 GYD per night
Guest favorite

Apartment in Superior

4.91 out of 5 average rating, 278 reviews

Terry Flats #4

Apr 10 – 17

G$22,821 GYD per night
Guest favorite

Cabin in Iron River

4.95 out of 5 average rating, 123 reviews

Log Cabin and Spider Lake

Nov 27 – Dec 4

G$33,706 GYD per night
Guest favorite

Apartment in Superior

4.83 out of 5 average rating, 376 reviews

Large 2 Bedroom near Lake Superior

Nov 16 – 23

G$27,584 GYD per night
Guest favorite

Home in Two Harbors

4.89 out of 5 average rating, 178 reviews

Two Harbors Area Wild Grape Cottage

Jan 23 – 30

G$20,927 GYD per night
Guest favorite

Cabin in Herbster

4.94 out of 5 average rating, 138 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

Apr 18 – 25

G$36,236 GYD per night
Guest favorite

Loft in Duluth

4.94 out of 5 average rating, 414 reviews

Experience Duluth Arts in the BB Makers Loft

May 26 – Jun 2

G$29,849 GYD per night
Guest favorite

Home in Duluth

4.95 out of 5 average rating, 448 reviews

Modern Outdoor Oasis

Apr 15 – 22

G$39,803 GYD per night
Guest favorite

Home in Superior

4.96 out of 5 average rating, 134 reviews

Cheerful 3 BR South Superior Family Home

Apr 1 – 8

G$33,792 GYD per night
Guest favorite

Shipping container in South Range

4.98 out of 5 average rating, 49 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Aug 7 – 14

G$80,715 GYD per night

Destinations to explore

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  5. Lakeside