New Chicago Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select New Chicago Vacation Homes

Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
Fridge, microwave, oven, stovetop

Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing

9.6 out of 10, Exceptional, (56)
"Amazing place to stay in a convenient location, we felt like we had a home away from home and Mickey was great about everything. "
The price is CA $119
CA $189 total
includes taxes & fees
Aug 22 - Aug 23
Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
The Bonnie Inn Unit 6
Terrace/patio

The Bonnie Inn Unit 6

3.0 star property
8.6 out of 10, Excellent, (9)
"I will definitely stay there again."
The price is CA $209
CA $288 total
includes taxes & fees
Aug 22 - Aug 23
The Bonnie Inn Unit 6
Wine Country Retreat-Beautiful Views-Family Fun
Terrace/patio

Wine Country Retreat-Beautiful Views-Family Fun

10.0 out of 10, Exceptional, (3)
"The home was a nice place for our stay while visiting our son for his graduation from UC Davis. We also wanted to visit lake tahoe while here. The home was clean and located in a quite location. Has a nice view of the hills nearby and we saw deer, rabbits, quail , and plenty of turkeys every day."
The price is CA $189
CA $409 total
includes taxes & fees
Aug 24 - Aug 25
Wine Country Retreat-Beautiful Views-Family Fun
Back of the Moon Cottage in the Hills
Smart TV, DVD player

Back of the Moon Cottage in the Hills

10.0 out of 10, Exceptional, (5)
"This was an outstanding home to stay in with my family. Centrally located for everything we wanted to do, extremely clean and welcoming. The garden and basketball court in the back was an amazing surprise! Will stay again when we return. "
The price is CA $198
CA $489 total
includes taxes & fees
Aug 31 - Sep 1
Back of the Moon Cottage in the Hills
A rejuvenating cabin in the woods
Property grounds

A rejuvenating cabin in the woods

10.0 out of 10, Exceptional, (4)
"It is a very cute house in a peaceful, mountain location. We enjoyed our time there, relaxing & host was very nice & responsive to questions that arose."
The price is CA $187
CA $386 total
includes taxes & fees
Sep 9 - Sep 10
A rejuvenating cabin in the woods
Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!
Property grounds

Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!

9.8 out of 10, Exceptional, (66)
"We had a great time. the beds were supper comfortable. i would definitely rent this place again."
The price is CA $270
CA $580 total
includes taxes & fees
Sep 18 - Sep 19
Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!
Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking
Pool

Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking

8.8 out of 10, Excellent, (8)
"Stayed for a disc golf tournament. A bed for everyone and lots of space outside to enjoy the weather and the pool/hot tub. Great communication from the host. Would love to stay again."
The price is CA $392
CA $727 total
includes taxes & fees
Aug 25 - Aug 26
Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Chicago Hotel Reviews

Red Hawk Resort & Casino

Red Hawk Resort & Casino

10/10 Excellent
"Everything was Good- "
Steven 2-night trip
Posted 1 day ago
Red Hawk Resort & Casino