Vacation rentals in Chicagon

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Top-rated vacation rentals in Chicagon

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

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Guest favorite

Home in Gaastra

4.81 out of 5 average rating, 139 reviews

"Yooper Retreat"

Cozy small-town house close to many of the activities Upper Peninsula Michigan has to offer. Time in the U.P. does not follow a clock, it is measured by your enjoyment. If you are looking for crystal palace, look elsewhere. This place offers the basic essentials in a typical Upper Peninsula small former mining community. Wi-Fi provided just in case the weather does not want to cooperate with your outdoor plans. Many of the floors recently upgraded. Bathroom updated to include shower/tub.

Sep 5 – 12

G$16,241 GYD per night

Guest favorite

Home in Crystal Falls

4.89 out of 5 average rating, 141 reviews

Crystal Falls Cozy Pet Friendly Home

Hello! Looking for a cozy home to stay while visiting the area? Look no further! 🏡Our home is located within walking distance to downtown, grocery store, Paint River/boat landings, gas stations, snowmobile and ATV trails. Only 20 minute drive to Ski Brule. Newly remodeled kitchen, new floors, trim and paint have recently been updated. FreeWiFi & new Central Air! Use the covered back deck to relax while letting the kids play in the huge back yard/sandbox in a quiet & kid friendly neighborhood.

Feb 22 – Mar 1

G$34,470 GYD per night

Superhost

Home in Iron Mountain

4.82 out of 5 average rating, 217 reviews

Cozy Home Away From Home!

Enjoy the Upper Peninsula~ Our place is in a very quiet neighborhood overlooking Lake Antoine~ ORV trails & Pine Mountain Ski Resort- fishing galore! Home is private to the guest. Queen bed, 1 bath, living area in lower level (a walk out basement); full kitchen and living space upper level. Our home has a 2 person Infrared Sauna, bar, washer & dryer, full kitchen & attached garage parking. Great for business people, couples, small families. Day bed available as well, but room is unfinished.

Oct 22 – 29

G$21,025 GYD per night

Guest favorite

Guesthouse in Sayner

4.97 out of 5 average rating, 152 reviews

Zen out & Sauna at LandsEndattheEdge Loft!

QUIET private zenny retreat! Covered deck in treetops overlooks NHAL state forest wilderness. Ponder a skyline of pines & a plethora of stars! Howling wolves & birdwatching; a vist by Woody, our resident pileated woodpecker sure to stop by. BBQ on gas grill, sit by firetable, or suhwing! Rustic sauna WIFI elect FP kitch 2kayaks. 5min to LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Lumberjack/Escanaba StateTrls, 15min to HeartofVilas paved 52+mi Trl. Semi-secluded yet 8mi to BJ restaurants!

Aug 31 – Sep 7

G$25,982 GYD per night

Guest favorite

Barn in Crandon

4.96 out of 5 average rating, 195 reviews

The Loft Above the Barn, Tamarack Moon,

Our place is a back-to-nature farm setting. . You’ll love our place because of the rustic location, the farm ambiance, and the beautiful outdoors. The Loft is comfortable for couples, solo adventurers, business travelers ,and families. It has one queen bed, one standard double bed and a couch . Dogs are welcome with prior approval/notification and there is a $15 dollar cleaning fee. Dogs must be leashed at all times for their safety (See further information under Neighborhood description)

Oct 7 – 14

G$22,483 GYD per night

Guest favorite

Cabin in Alvin

4.87 out of 5 average rating, 168 reviews

Rivers reach

Our cabin is located in the heart of the Nicolet national forest on 37.5 acres It boarders on two sides creating a beautiful and very peaceful setting. Once inside you will feel warm and comfortable while being able to see all the beauty nature has to offer through all the windows over looking the property. Plenty of space in the kitchen to prepare a meal or relax on the deck while grilling. Relax by the camp fire or cool off in the pond. Snowmobile and atv trails through back of property.

Sep 24 – Oct 1

G$21,242 GYD per night

Guest favorite

Cabin in Town of Silver Cliff

5.0 out of 5 average rating, 144 reviews

Hardwood Hideaway Cabin on the Peshtigo River

Medium size cabin on 2 acre wooded lot overlooking Peshtigo River. On snowmobile trail&ATV route on Cnty Rd C. Walking distance to 2 pubs. Close to Kosirs Rafting/ Wildmans Adventure Resort. On Private road. Parking area for trailers and boats. Well lit outdoor space at night. Fire pit & wood. 2 boat launches at Caldron Falls within a mile. WiFi/Netflix included. Short trail to the river. All cotton bedding and towels. Quality cookware & supplies. Fresh eggs. No Cleaning Fee! Pets Welcome!

Aug 7 – 14

G$34,379 GYD per night

Guest favorite

Cabin in Crivitz

4.99 out of 5 average rating, 122 reviews

Scenic, Serene Lakefront Cabin — Wood Stove

Nestled on the tranquil Grass Lake, your cozy cabin retreat awaits! Whether enjoying yard games, the crackling bonfire, or the snug embrace of the wood stove, this space is thoughtfully crafted for your next family getaway or peaceful solo escape. Bask in the breathtaking lakefront views from the dock, deck, or four-seasons room. Immerse yourself in a space designed to foster connections and spark creativity. We welcome you to join us and create your own beautiful memories at the cabin.

Mar 3 – 10

G$24,933 GYD per night

Guest favorite

Cottage in Iron Mountain

4.82 out of 5 average rating, 112 reviews

Antoine Lake House

Two bedroom home across the street from Lake Antoine with lake access. Come relax with an indoor fireplace, watch the gorgeous lake views and have access to hundreds of miles of UTV/Snowmobile and Bike trails right from the house. Ice fishing and fishing galore within minutes from town and within 5 miles to Pine Mountain Ski Resort, Timberstone Golf Course and True North Outpost. Within an hour drive from Ski Brule. Newly remodeled home with parking in garage and driveway for toys!

Aug 9 – 16

G$21,451 GYD per night

Guest favorite

Cabin in Crivitz

4.96 out of 5 average rating, 305 reviews

Whippoorwill Valley Cabin quiet waterfront cabin

Scenically situated overlooking the water, our peaceful 2 bedroom cabin is located directly on the waters of the Johnson Falls Flowage. Perfect for nature lovers who love the quiet calm of the north woods. Kayak, fish or sit by the water right from the cabin shores. We are close to numerous State & County Parks, Boat launches, ATV/Snowmobile trails & more! The fire pit provides endless entertainment. Nature abounds with deer, turkeys, eagles, bears and much more!

Dec 7 – 14

G$33,561 GYD per night

Guest favorite

Apartment in Florence

4.95 out of 5 average rating, 131 reviews

Secluded Spread Eagle Sanctuary

Executive home nestled in a private sanctuary of unique trees and shrubs. A piece of paradise greets you with a tree shaded drive. Outside parking space for a boat, trailer, etc. Private entrance into a furnished 14x24 bedroom with full bathroom, great room w/ 52" tv wifi and second split king size bed, open access to home with privacy. Patio doors onto patio with a fire pit overlooking the river. In-floor heat, central air. We have 2 sweet golden retrievers.

Sep 17 – 24

G$16,951 GYD per night

Guest favorite

Cabin in Iron River

4.92 out of 5 average rating, 49 reviews

Ski Brule Log Cabin

Enjoy memorable mountain views at this lovable 3BR cabin, located just a 5-minute walk from the Ski Brule lifts. Fire up the gas grill and host a cookout on the scenic back deck. Sleeps 9. Located just a 5-minute walk from the Ski Brule base, this lovable 3BR/3BA cabin presents memorable mountain views and an unbeatable slopeside setting. Whip up delicious dishes in the well-equipped kitchen or fire up the gas grill and host an afternoon cookout.

May 4 – 11

G$25,227 GYD per night