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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 15 – 22

$100 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.

Dec 31 – Jan 7

$75 per night
Guest favorite

Guest suite in Brule

4.97 out of 5 average rating, 135 reviews

The Bee's Balm

You'll find us tucked in the quiet woods of northern WI near the Brule River. We're remote enough to experience star-filled skies & fireflies, but not far from many premier attractions. Your space is a self-contained apartment on the lower level of our 2.5 story home. It features a private entry, queen-sized bed, kitchenette, lower level private deck, access our beautiful grounds & more! We're a family of artists who love to travel & to introduce others to our beautiful part of the world.

Nov 13 – 20

$87 per night

Popular amenities for Lakeside vacation rentals

Other great vacation rentals in Lakeside

Guest favorite

Cottage in Herbster

4.98 out of 5 average rating, 209 reviews

Lake Superior's Cranberry River Cottage- The Raven

Feb 8 – 15

$106 per night
Guest favorite

Cottage in Lake Nebagamon

5.0 out of 5 average rating, 124 reviews

Guest House at the Lake

May 19 – 26

$135 per night
Guest favorite

Apartment in Superior

4.91 out of 5 average rating, 278 reviews

Terry Flats #4

May 28 – Jun 4

$98 per night
Guest favorite

Home in Two Harbors

4.89 out of 5 average rating, 178 reviews

Two Harbors Area Wild Grape Cottage

Dec 17 – 24

$87 per night
Guest favorite

Cabin in Iron River

4.95 out of 5 average rating, 123 reviews

Log Cabin and Spider Lake

Nov 29 – Dec 6

$140 per night
Guest favorite

Apartment in Superior

4.83 out of 5 average rating, 376 reviews

Large 2 Bedroom near Lake Superior

Dec 5 – 12

$115 per night
Guest favorite

Apartment in Hermantown

4.79 out of 5 average rating, 652 reviews

Beautiful, private vacation space

Nov 23 – 30

$89 per night
Superhost

Cabin in Gordon

4.93 out of 5 average rating, 106 reviews

The Gordon Flowage Cabin

Feb 23 – Mar 2

$121 per night
Guest favorite

Home in Superior

4.96 out of 5 average rating, 134 reviews

Cheerful 3 BR South Superior Family Home

Sep 5 – 12

$140 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

$150 per night
Guest favorite

Home in Duluth

4.95 out of 5 average rating, 448 reviews

Modern Outdoor Oasis

Apr 15 – 22

$165 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 31 – Sep 7

$317 per night

Destinations to explore

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  2. United States
  3. Wisconsin
  4. Douglas County
  5. Lakeside