Vacation rentals in Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chicago

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

Superhost

Cabin in Medina

4.89 out of 5 average rating, 9 reviews

Lakeside Oasis

Relax with the whole family at this peaceful retreat at Reule Lake. Peaceful mornings and fun-filled days await you. This brand new development has all you need to enjoy ND summers. Water and beach access right out your front door. Enjoy an afternoon on the dock relaxing or fishing, dinner on the deck, or board games in the living room. So many memories to be had. During the fall enjoy abundant waterfowl, upland hunting until your heart’s content. Please be mindful this is a new development.

Aug 1 – 8

R5,594 ZAR per night
Guest favorite

Cabin in Jamestown

4.98 out of 5 average rating, 49 reviews

Little Earth Lodge, ND. Ice Fishermen Welcome!

Bring your family and friends to this great place with lake access, massive deck, fire pit, ample parking, spacious kitchen, and large gathering areas. Little Earth Lodge offers the best accommodations in Stutsman County and is located right on the waters edge. •You will enjoy watching the wildlife and fishing right off of your own private dock. •Several outdoor games are available including a beautiful pool table upstairs. •A canoe and paddle boards is provided for your lake fun recreation!

Jun 13 – 20

R9,801 ZAR per night
Guest favorite

Home in Jamestown

4.95 out of 5 average rating, 154 reviews

Rust House Inn, Updated Arts and Crafts Style Home

Rust House Inn is an Arts and Crafts style home built in 1925. Updated in a modern farmhouse style it showcases architectural details including white maple floors. You will find comfort and coziness in every niche with plenty of space to unwind. The kitchen is a chef's dream. The award winning yard is a perfect place to relax. Sea salt hot tub and fire pit are favorite amenities. Restaurants, coffee shops and pubs are a short walk away, making the home's location perfect. No parties or events.

Nov 7 – 14

R4,479 ZAR per night

Popular amenities for Chicago vacation rentals

Other great vacation rentals in Chicago

Guest favorite

Home in Jamestown

4.94 out of 5 average rating, 33 reviews

Spacious, comfortable 5 Bedroom home in Jamestown!

Sep 26 – Oct 3

R4,360 ZAR per night
Superhost

Home in Gackle

4.88 out of 5 average rating, 8 reviews

The Nest in Gackle, ND

Aug 19 – 26

R8,698 ZAR per night
Superhost

Apartment in Cooperstown

4.87 out of 5 average rating, 39 reviews

"The Family" - Entire private 2 bed/ 2 bath Apt

Apr 14 – 21

R1,895 ZAR per night
Superhost

Home in Ashley

5.0 out of 5 average rating, 3 reviews

Upper Level Lodge Sleeps 9!

Sep 29 – Oct 6

R1,109 ZAR per night
Guest favorite

Cottage in Wimbledon

4.95 out of 5 average rating, 60 reviews

The Prairie Cottage (Bethany Prairie School)

Aug 11 – 18

R2,926 ZAR per night
Superhost

Home in Ashley

4.67 out of 5 average rating, 3 reviews

Plenty of Room for all !!!

Jan 31 – Feb 7

R1,807 ZAR per night
Guest favorite

Home in Carrington

4.91 out of 5 average rating, 22 reviews

Pipestem Creek Garden Lodging. Longspur House

Feb 4 – 11

R3,280 ZAR per night

Home in Medina

4.71 out of 5 average rating, 7 reviews

Medina Hunting House

Aug 10 – 17

R1,119 ZAR per night
Guest favorite

Cabin in Cleveland

4.88 out of 5 average rating, 67 reviews

Hideaway Lodge

Jan 13 – 20

R3,477 ZAR per night

Vacation home in Medina

4.67 out of 5 average rating, 3 reviews

Hunting and Fishing rental house. Medina ND.

Aug 5 – 12

R3,604 ZAR per night

Apartment in Medina

4.75 out of 5 average rating, 12 reviews

Beautiful suite just off i-94!

Aug 28 – Sep 4

R3,226 ZAR per night
Guest favorite

Home in Gackle

5.0 out of 5 average rating, 7 reviews

Outdoor Getaway

Feb 8 – 15

R5,397 ZAR per night

Destinations to explore

  1. Airbnb
  2. United States
  3. North Dakota
  4. Stutsman County
  5. Chicago