New Chicago Holiday Rentals

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Check prices for these dates

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Holiday Rentals in New Chicago

Room, 1 Queen Bed, Garden View | View from room
The Bonnie Inn Unit 6
The Bonnie Inn Unit 6
3.0 star property
8.6 out of 10, Excellent, (9)
"I will definitely stay there again."
United States
Karyn
The Bonnie Inn Unit 6
Fridge, microwave, oven, stovetop
Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
9.6 out of 10, Exceptional, (61)
"This rental is clean, quiet, and comfortable. The view is beautiful and the morning sun came in through the large windows. We enjoyed sitting on patio and watching the deer."
United States
Candace
The price is AU$204
includes taxes & fees
26 Oct - 27 Oct
Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
Property grounds
Cottage amongst the vines in the heart of Fair Play wine country
Cottage amongst the vines in the heart of Fair Play wine country
10.0 out of 10, Exceptional, (59)
"Cottage was nice and clean"
United States
Jeff
The price is AU$367
includes taxes & fees
27 Oct - 28 Oct
Cottage amongst the vines in the heart of Fair Play wine country
Property grounds
Relaxing cabin in the woods. Unplug. Listen to the birds. Smell the pines.
Relaxing cabin in the woods. Unplug. Listen to the birds. Smell the pines.
9.6 out of 10, Exceptional, (11)
"Great location, safe and beautiful scenery "
United States
Lauren E.
The price is AU$315
includes taxes & fees
26 Oct - 27 Oct
Relaxing cabin in the woods. Unplug. Listen to the birds. Smell the pines.
Exterior
Beautiful Rustic Cabin on 5 Acres With Heavenly Views
Beautiful Rustic Cabin on 5 Acres With Heavenly Views
9.2 out of 10, Wonderful, (15)
"Stayed there for 3 days. It’s a beautiful property, a lot of vegetation and trees. It’s a large property, thinking of going back again in the winter "
United States
blablablabla h.
The price is AU$1,070
includes taxes & fees
3 Nov - 4 Nov
Beautiful Rustic Cabin on 5 Acres With Heavenly Views
Property grounds
Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!
Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!
9.8 out of 10, Exceptional, (69)
"We had a great time. the beds were supper comfortable. i would definitely rent this place again."
United States
JON B.
The price is AU$625
includes taxes & fees
27 Oct - 28 Oct
Farmhouse with Hot Tub, charming gardens, serenity, 2 blocks to Main Street!
Fridge, microwave, oven, stovetop
NEW: 3BR, private HotTub, FireTable, BBQ, AC, Dogs OK, WIFI
NEW: 3BR, private HotTub, FireTable, BBQ, AC, Dogs OK, WIFI
2.5 star property
10.0 out of 10, Exceptional, (1)
"Great house with lots of extra perks like plenty of kitchen gadgets, clearly labeled switches, and overall a well maintained and cozy home. Hosts were responsive and helpful!"
United States
Crystal E.
The price is AU$609
includes taxes & fees
26 Oct - 27 Oct
NEW: 3BR, private HotTub, FireTable, BBQ, AC, Dogs OK, WIFI
Property grounds
A rejuvenating cabin in the woods
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."
United States
Lucy L.
The price is AU$437
includes taxes & fees
2 Nov - 3 Nov
A rejuvenating cabin in the woods
Outdoor dining
Lovely 1-bedroom cabin in Pioneer plus camping and Rv Sites w/ 10 person hot tub
Lovely 1-bedroom cabin in Pioneer plus camping and Rv Sites w/ 10 person hot tub
The price is AU$382
includes taxes & fees
27 Oct - 28 Oct
Lovely 1-bedroom cabin in Pioneer plus camping and Rv Sites w/ 10 person hot tub
Terrace/patio
Beautiful 2 bedroom 2 bath Vineyard house located in a vineyard on 40 acres
Beautiful 2 bedroom 2 bath Vineyard house located in a vineyard on 40 acres
2.0 star property
The price is AU$1,105
includes taxes & fees
28 Oct - 29 Oct
Beautiful 2 bedroom 2 bath Vineyard house located in a vineyard on 40 acres
Exterior
Cozy 1-bedroom apartment in welcoming Pioneer with WiFi, AC. Close to Kirkwood.
Cozy 1-bedroom apartment in welcoming Pioneer with WiFi, AC. Close to Kirkwood.
9.4 out of 10, Exceptional, (3)
"Great and convienent place to stay. "
United States
Brian M.
The price is AU$298
includes taxes & fees
5 Nov - 6 Nov
Cozy 1-bedroom apartment in welcoming Pioneer with WiFi, AC. Close to Kirkwood.
Pool
Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking
Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking
8.8 out of 10, Excellent, (9)
"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."
United States
Nathaniel M.
The price is AU$808
includes taxes & fees
27 Oct - 28 Oct
Pool-2 King Beds-Hot Tub-Fire Place-Garage Parking
Smart TV, DVD player
Back of the Moon Cottage in the Hills
Back of the Moon Cottage in the Hills
10.0 out of 10, Exceptional, (6)
"This was the perfect little house for our trip out to see family in placerville. It was clean, convenient and communication with host was great. Love the little touches they have put into this place including the garden in the backyard. My three year old loved the books and games. Would stay here again. "
United States
Kayla L.
The price is AU$589
includes taxes & fees
16 Nov - 17 Nov
Back of the Moon Cottage in the Hills
Interior
Wine Country Retreat - Monarch Trails
Wine Country Retreat - Monarch Trails
9.8 out of 10, Exceptional, (7)
"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."
United States
Jeffrey K.
The price is AU$475
includes taxes & fees
27 Oct - 28 Oct
Wine Country Retreat - Monarch Trails
2 bedrooms, WiFi, bed sheets
20 acre luxury glamping grounds
20 acre luxury glamping grounds
2.0 out of 10, (3)
"It’s a scam. There’s nothing on the property and host does not respond."
United States
Ken B.
The price is AU$381
includes taxes & fees
2 Nov - 3 Nov
20 acre luxury glamping grounds
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.
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Top New Chicago Hotel Reviews

National Hotel Jackson, Tapestry Collection by Hilton

National Hotel Jackson, Tapestry Collection by Hilton

10/10 Excellent
"Staff were wonderful from the time we arrived till we checked out. Our room was beautiful and comfortable and very quiet. We enjoyed all the Halloween decor that added such a nice touch for this time of year. We will definitely stay again when in the area."
Donna 1-night trip
Posted 3 days ago
National Hotel Jackson, Tapestry Collection by Hilton

Find out more about New Chicago

Everything you need to know about New Chicago holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Chicago holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Chicago holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

New Chicago holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Chicago. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Chicago holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Chicago holiday rentals we have selected for you start as low as AU$204 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on New Chicago rentals

At Expedia, we put the best New Chicago holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top New Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Chicago holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in New Chicago?

Yes, there are holiday rentals close to the most popular sights in New Chicago, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that New Chicago has to offer?

A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna. : This holiday home rental outside of New Chicago is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in New Chicago?

While exploring the area, visit family-friendly sights like Sutter Creek Cheese Shoppe, or get outside and enjoy nature at Black Chasm Cavern National Landmark. Sutter Creek Wine Tasting and Sutter Creek Theater are a couple of places you'll find in the wider area.

What are holiday rentals like in New Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Chicago. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.