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Vacation rentals in Chicagon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chicagon

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

Guesthouse in Sayner
Zen out & Sauna at LandsEndattheEdge Loft!
QUIET zenny retreat! Off seas discounts Nov-mid Dec. Snowshoe out the door. Covered/screened deck in treetops overlooks NHAL st forest. Immerse yourself in nature! BBQ on gas grill, swing/sit by fire table. Rustic sauna steps away. WIFI FP kitch, 4 yaks, 2 pr snowshoes. 5min to Lost Canoe, White Sand, Lumberjack Trl. 15min to 52+mi HeartofVilas paved bike trl. 10Lakes10min, 2in5. Semi-seclud yet 8mi to good coff/eats! Dont ya wanna sauna? Need more space? See our Hygge or NorthNirvana listings
$95 per night
Home in Crystal Falls
Crystal Falls Pet (with fee) Friendly Cozy 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.
$160 per night
Home in Gaastra
"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.
$72 per night

Other great vacation rentals in Chicagon

Home in Caspian
Cozy house on snowmobile trail close to ski hills
$75 per night
Home in Iron River
U P Hideaway
$109 per night
Home in Iron River
Secluded Lakehouse w/ Private Dock + Serene Views!
$204 per night
Apartment in Iron River
Fairview School House 2 Bedroom Apartment
$96 per night
Cottage in Crystal Falls
Cozy lakefront cottage near snowmobile trails
$157 per night
Guesthouse in Crystal Falls
Runkle Lake Retreat
$106 per night
Cabin in Iron River
Lone Pine: Book your ski trip early!
$92 per night
Cottage in Iron River
Sunset Lake - Fireplace|Dock|Sauna|4 Bath|Ski|UTV
$250 per night
Cabin in Iron River
Ski Brule Log Cabin
$100 per night
Home in Iron River
The Ice House - An UPscale U.P. lake home
$300 per night
Apartment in Gaastra
UP getaway in Caspian/Iron River
$81 per night
Home in Iron River
Cozy 2 bed/2 bath home
$170 per night

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  5. Chicagon