New Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for New Chicago vacation rentals

A building with a white exterior and a brick pathway.

1. Farmhouse w Hot Tub, charming gardens, serenity, walk to Main Street! EV Charger

Farmhouse w Hot Tub, charming gardens, serenity, walk to Main Street! EV Charger
Jackson
9.8 out of 10, Exceptional, (80 reviews)
"This was one of the most charming rental homes we’ve stayed in. Easy walk to the cute downtown which happened to have a great restaurant for gluten-free/celiac eating. The garden and hot tub under the wisteria were just magical. Well stocked, comfortable and a real “piece of Jackson history”. Will absolutely be renting again."
United States
Annie R.
The price is CA $272
CA $601 total
includes taxes & fees
Nov 16 - Nov 17
Farmhouse w Hot Tub, charming gardens, serenity, walk to Main Street! EV Charger
Pool

2. Cozy 1-bedroom condo with AC, WiFi in charming Amador City

Cozy 1-bedroom condo with AC, WiFi in charming Amador City
Amador City
The price is CA $169
CA $335 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 1-bedroom condo with AC, WiFi in charming Amador City
A residential property with a backyard waterfall, a swimming pool, and a house with a balcony.

3. Rockslide Pool+Hot Tub+Fire pit | Luxury Estate

Rockslide Pool+Hot Tub+Fire pit | Luxury Estate
Sutter Creek
9.6 out of 10, Exceptional, (21 reviews)
"We had the best time! The host was on top of responses and made our stay worry free! I highly recommend staying here!"
United States
Taylor S.
The price is CA $1,258
CA $2,473 total
includes taxes & fees
Nov 6 - Nov 7
Rockslide Pool+Hot Tub+Fire pit | Luxury Estate
A couple sitting on a wooden bench outside a rustic cabin with a coffee pot and mug on the table.

4. Iglunest Retreat, Sauna, Views & Nature

Iglunest Retreat, Sauna, Views & Nature
Sutter Creek
The price is CA $345
CA $637 total
includes taxes & fees
Nov 30 - Dec 1
Iglunest Retreat, Sauna, Views & Nature
A house with a large porch and multiple windows, surrounded by trees and a body of water.

5. Lakefront with 4 Ensuites by 10 wineries

Lakefront with 4 Ensuites by 10 wineries
Shenandoah Valley
The price is CA $520
CA $1,399 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront with 4 Ensuites by 10 wineries
A two-story house with a front porch, a mailbox, and a well-maintained lawn.

6. Boho Farmhouse in Historic Gold Country: Great for Large Families or Groups!

Boho Farmhouse in Historic Gold Country: Great for Large Families or Groups!
Mokelumne Hill
The price is CA $278
CA $674 total
includes taxes & fees
Nov 8 - Nov 9
Boho Farmhouse in Historic Gold Country: Great for Large Families or Groups!
A patio with a table set for a meal, featuring a book, grapes, and cheese.

7. Monarch Trails · Wine Country Retreat

Monarch Trails · Wine Country Retreat
Somerset
9.4 out of 10, Exceptional, (14 reviews)
"Great stay."
United States
Susan M.
The price is CA $237
CA $478 total
includes taxes & fees
Nov 10 - Nov 11
Monarch Trails · Wine Country Retreat
A reception desk with a staff member, a guest, and a child.

8. 1 Queen Bed | N-S, Kitchen, SB

1 Queen Bed | N-S, Kitchen, SB
Cameron Park
10.0 out of 10, Exceptional, (54 reviews)
"Really appreciated how relaxed the whole place felt!"
United States
Anonymous traveller
The price is CA $159
CA $178 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | N-S, Kitchen, SB
A forested area with tall trees and a dirt ground.

9. 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.
Pioneer
9.6 out of 10, Exceptional, (32 reviews)
"House was great for a one night stay in pioneer. Quiet and roomy."
United States
Julie
The price is CA $154
CA $236 total
includes taxes & fees
Nov 16 - Nov 17
Relaxing cabin in the woods. Unplug. Listen to the birds. Smell the pines.
Pool- Yes! We love our guests to use it!

10. Luxury Cabin on 10 acre Ranch (Pet Friendly)

Luxury Cabin on 10 acre Ranch (Pet Friendly)
Ione
The price is CA $265
CA $367 total
includes taxes & fees
Nov 12 - Nov 13
Luxury Cabin on 10 acre Ranch (Pet Friendly)
A modern kitchen with a central island, white cabinets, and a wooden countertop.

11. Charming Fair Play Cottage near local wineries

Charming Fair Play Cottage near local wineries
Somerset
9.4 out of 10, Exceptional, (19 reviews)
"Perfect getaway"
United States
Matthew L.
The price is CA $238
CA $449 total
includes taxes & fees
Nov 16 - Nov 17
Charming Fair Play Cottage near local wineries
A rustic cabin with a wooden exterior, a porch with seating, and string lights.

12. Luxury Private TINY HOUSE on 10 Remote Acres

Luxury Private TINY HOUSE on 10 Remote Acres
Ione
8.0 out of 10, Very good, (4 reviews)
"I requested a date change the same day that I requested to stay they still build for the dates that I did not request. Imy updated request dates are the 1st - 4th of aug"
United States
Benjamin R.
The price is CA $201
CA $305 total
includes taxes & fees
Nov 10 - Nov 11
Luxury Private TINY HOUSE on 10 Remote Acres
A single-story house with a beige exterior, a white front door with a heart-shaped window, and a small window above the door.

13. CHUCKELLI FARM's COZY COTTAGE

CHUCKELLI FARM's COZY COTTAGE
Placerville
10.0 out of 10, Exceptional, (88 reviews)
"Sweet and peaceful place. Great location for the places I had planned to visit."
United States
Kristina S.
The price is CA $151
CA $229 total
includes taxes & fees
Nov 12 - Nov 13
CHUCKELLI FARM's COZY COTTAGE
A bedroom with a fireplace, a bed, a window, and a door.

14. 'hidden Valley Retreat' - Outdoorsy West Point Gem

'hidden Valley Retreat' - Outdoorsy West Point Gem
3.0 star property
West Point
10.0 out of 10, Exceptional, (1 review)
"This little cabin was perfect! You can see the main house from the driveway and front door, but with the direction of the home and an umbrella, you feel like you're all by yourself in the woods. There are some pups, but they were well behaved and didn't come around often. This is a great little cabin—perfect for a 2 person get-away—with all the amenities you will need. There was a coffee maker and tea, grill on the patio, and we were able to cook breakfast and dinner each day of our stay with...
United States
Tara
The price is CA $133
CA $341 total
includes taxes & fees
Nov 8 - Nov 9
'hidden Valley Retreat' - Outdoorsy West Point Gem
An outdoor patio with a grill, chairs, and a shaded area.

15. Explore Amador & Calaveras Counties. Kirkwood 45 minutes away.

Explore Amador & Calaveras Counties. Kirkwood 45 minutes away.
West Point
9.6 out of 10, Exceptional, (34 reviews)
"The property was clean, everything was easy to find, the beds were really comfortable and we really enjoyed our stay there. Thank you so much!"
United States
Britt
The price is CA $171
CA $288 total
includes taxes & fees
Nov 9 - Nov 10
Explore Amador & Calaveras Counties. Kirkwood 45 minutes away.
A hot tub with three people, surrounded by trees and string lights.

16. Modern House: w/ HotTub, FireTable, BBQ, Games, Wine Testing!

Modern House: w/ HotTub, FireTable, BBQ, Games, Wine Testing!
Pioneer
10.0 out of 10, Exceptional, (5 reviews)
"The home was very clean, with plenty of seating, and the hot tub was an especially a big hit! The welcome basket was so nice and we enjoyed the extra decorations and holiday lighting which gave a nice cozy vibe."
United States
Jason R.
The price is CA $291
CA $657 total
includes taxes & fees
Nov 30 - Dec 1
Modern House: w/ HotTub, FireTable, BBQ, Games, Wine Testing!
A bedroom with a bed, a sofa, a table, and a fireplace.

17. Vintage French Farmhouse charm in the countryside

Vintage French Farmhouse charm in the countryside
Placerville
9.8 out of 10, Exceptional, (9 reviews)
"This place was so cozy and perfect for a weekend getaway!"
United States
Haley M.
The price is CA $145
CA $280 total
includes taxes & fees
Nov 18 - Nov 19
Vintage French Farmhouse charm in the countryside
A deck with outdoor furniture, a fire pit, and a glass wall overlooking a forest.

18. Luxury Forest Couple Retreat with Hot Tub, Cold Plunge, Outdoor Movie, Firepit

Luxury Forest Couple Retreat with Hot Tub, Cold Plunge, Outdoor Movie, Firepit
West Point
The price is CA $301
CA $683 total
includes taxes & fees
Nov 15 - Nov 16
Luxury Forest Couple Retreat with Hot Tub, Cold Plunge, Outdoor Movie, Firepit
A spacious kitchen with white cabinets, granite countertops, and a wooden floor.

19. 🏔️ Hilltop Paradise with Pool & Hot Tub | 4BR Near Apple Hill

🏔️ Hilltop Paradise with Pool & Hot Tub | 4BR Near Apple Hill
Diamond Springs
9.0 out of 10, Wonderful, (12 reviews)
"A great location to go east to Lake Tahoe or west to wineries."
United States
David D.
The price is CA $445
CA $780 total
includes taxes & fees
Nov 9 - Nov 10
🏔️ Hilltop Paradise with Pool & Hot Tub | 4BR Near Apple Hill
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

A reception desk with a sign reading "National Hotel NH" and a "Registration" sign.
National Hotel Jackson, Tapestry Collection by Hilton

National Hotel Jackson, Tapestry Collection by Hilton

National Hotel Jackson, Tapestry Collection by Hilton
Downtown Jackson

10/10 Excellent

If you want something different than your generic hotel, this is your place. Service was great. Location to fun shopping was excellent.
Canada
Carol
Reviewed November 20, 2023
National Hotel Jackson, Tapestry Collection by Hilton

Find out more about New Chicago

Everything you need to know about New Chicago vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Chicago vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Chicago vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Chicago vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Chicago vacation rentals we have selected for you start as low as CA $35 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Chicago rentals

At Expedia, we put the best New Chicago vacation 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 vacation.

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 vacation rentals in New Chicago?

Yes, we give you a choice of vacation rentals close to well known sights in New Chicago, or you can go with a secluded option if you're looking for relaxation.

What's the top vacation rental in New Chicago?

A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna. : You might want to consider this vacation home rental near New Chicago, which is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Bryson Park. Sutter Creek Theater and Sutter Creek City Hall are a couple of places you'll find in the larger area.

What are vacation rentals like in New Chicago?

Vacation rentals are private properties you can book for a short or long stay in New Chicago. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip.