New Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in New Chicago

Last-Minute August Deal! 20% Off + Fiber WiFi, Hot Tub, Pets Ok, Alpine Lakes
Smart TV, video games, toys, books

Last-Minute August Deal! 20% Off + Fiber WiFi, Hot Tub, Pets Ok, Alpine Lakes

10.0 out of 10, Exceptional, (19)
"Enjoyed the relaxing stay"
Last-Minute August Deal! 20% Off + Fiber WiFi, Hot Tub, Pets Ok, Alpine Lakes
CHUCKELLI FARM's COZY COTTAGE
Property grounds

CHUCKELLI FARM's COZY COTTAGE

10.0 out of 10, Exceptional, (64)
"The property was gorgeous and cottage was decorated beautifully. The host was responsive in our communication and would definitely consider returning."
$149 nightly
The price is $162
Sep 7 - Sep 8
Total with taxes and fees
CHUCKELLI FARM's COZY COTTAGE
Welcome to Sunset Hills Ranch!
Outdoor pool

Welcome to Sunset Hills Ranch!

10.0 out of 10, Exceptional, (115)
"Everything was great. Only thing that needs improvement was the two barking dogs at night. "
Welcome to Sunset Hills Ranch!
Wine Country Retreat-Beautiful Views-Family Fun
Terrace/patio

Wine Country Retreat-Beautiful Views-Family Fun

9.6 out of 10, Exceptional, (5)
"Three friends of 50 yrs- had a great weekend, enjoyed that wine country, rental was very comfortable and we enjoyed it so much!"
$291 nightly
The price is $291
Sep 9 - Sep 10
Total with taxes and fees
Wine Country Retreat-Beautiful Views-Family Fun
Pet-Friendly Jackson Wine Country Home w/ Pool!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Jackson Wine Country Home w/ Pool!

9.4 out of 10, Exceptional, (30)
"Great stay! The home was clean, relaxing and exactly as advertised. Would definitely stay again."
Pet-Friendly Jackson Wine Country Home w/ Pool!
Charming Creekside Country Home
Outdoor spa tub

Charming Creekside Country Home

9.0 out of 10, Wonderful, (30)
"Every thing was just as advertised. Great stay in the hills with wonderful seclusion. Quite, where one can be with nature. We loved hearing the wild turkeys and creek off in the distance. Easy drive to and from town. Park and load/unload right at the front door. Hot tub was wonderful. ."
Charming Creekside Country Home
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. "
$324 nightly
The price is $352
Sep 9 - Sep 10
Total with taxes and fees
Back of the Moon Cottage in the Hills
Serenity Ridge A Unique Property - Entire Home in Diamond Springs, California
Exterior

Serenity Ridge A Unique Property - Entire Home in Diamond Springs, California

9.8 out of 10, Exceptional, (6)
"Just as advertised, it was a wonderful house and beautiful quiet property. The kids had a great time too playing basket ball and running the maze!"
Serenity Ridge A Unique Property - Entire Home in Diamond Springs, California
Quail Meadows Ranch Home, 32+ acres of land, spectacular views
Outdoor pool

Quail Meadows Ranch Home, 32+ acres of land, spectacular views

10.0 out of 10, Exceptional, (59)
"Comfortable, lots of room, beautiful kitchen/dining facilities."
Quail Meadows Ranch Home, 32+ acres of land, spectacular views
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, (57)
"Amazing place to stay in a convenient location, we felt like we had a home away from home and Mickey was great about everything. "
$126 nightly
The price is $136
Sep 8 - Sep 9
Total with taxes and fees
Sleeps 4 - Near Plymouth Wineries, Jackson Casino, Sutter Creek, Kirkwood Skiing
Cottage amongst the vines in the heart of Fair Play wine country
Property grounds

Cottage amongst the vines in the heart of Fair Play wine country

10.0 out of 10, Exceptional, (57)
"So glad we met the owners and learned about this property. It was every thing it was supposed to be and conveniently located to numerous wineries for our wine tasting weekend. "
$217 nightly
The price is $237
Sep 8 - Sep 9
Total with taxes and fees
Cottage amongst the vines in the heart of Fair Play wine country
A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.
Exterior

A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.

9.8 out of 10, Exceptional, (186)
"Loved our stay"
A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.
Luxury 5 Bedroom 4.5 Bath Dream Estate with Resort-like Pool In Wine Country
Exterior

Luxury 5 Bedroom 4.5 Bath Dream Estate with Resort-like Pool In Wine Country

9.6 out of 10, Exceptional, (18)
"We had the best time! The host was on top of responses and made our stay worry free! I highly recommend staying here!"
Luxury 5 Bedroom 4.5 Bath Dream Estate with Resort-like Pool In Wine Country
Sleeps 12 Pet Friendly Next to Amador Top Wineries
Terrace/patio

Sleeps 12 Pet Friendly Next to Amador Top Wineries

10.0 out of 10, Exceptional, (20)
"This beautiful house was exactly as listed. Ideally located for wine tasting in the Shenandoah Valley, fully equipped with all our needs. A large chef's kitchen with everything we needed. Beautiful views from the patio overlooking the vineyards behind the house. We will be back!"
Sleeps 12 Pet Friendly Next to Amador Top Wineries
Wine Lovers’ Garden Oasis in Sutter Creek!
Fridge, microwave, stovetop, coffee/tea maker

Wine Lovers’ Garden Oasis in Sutter Creek!

9.4 out of 10, Exceptional, (38)
"Great place to unwind after a day wine tasting."
Wine Lovers’ Garden Oasis in Sutter Creek!
Peaceful pet & family friendly MotherLode Cabin - steps to historic Sutter Creek
Fridge, microwave, oven, stovetop

Peaceful pet & family friendly MotherLode Cabin - steps to historic Sutter Creek

9.8 out of 10, Exceptional, (16)
"Quiet, beautiful, comfortable what else could we want?"
Peaceful pet & family friendly MotherLode Cabin - steps to historic Sutter Creek
Sizzling Summer Sale at Halcyon House!
Fridge, microwave, oven, stovetop

Sizzling Summer Sale at Halcyon House!

10.0 out of 10, Exceptional, (94)
"We had a wonderful stay. The house is nicely decorated well appointed and very clean. "
Sizzling Summer Sale at Halcyon House!
Stylish Home, Stunning Views and Private Hot Tub!
Outdoor spa tub

Stylish Home, Stunning Views and Private Hot Tub!

10.0 out of 10, Exceptional, (14)
"The home was everything we were looking for, comfortable, friendly, clean and perfect mountain location. The landscaping was beautiful, iris, roses, lilacs, and a wonderful lawn area for kids to run! "
Stylish Home, Stunning Views and Private Hot Tub!
3 BR Home - Close to Highway & Amenities
Dining

3 BR Home - Close to Highway & Amenities

3 BR Home - Close to Highway & Amenities
Wine Lovers Garden Oasis in Sutter Creek!
House (3 Bedrooms) | Interior

Wine Lovers Garden Oasis in Sutter Creek!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was great for a girls weekend in the wine country. Definitely more suitable for sleeping 6, can't imagine 8 adults would be comfortable. The communication was great. There are just a few simple touches that would make it a 5 star stay, such as adult sized bath towels, stocked toliet paper, and a full set of wine glasses (since it's the wine country). We cooked dinner both nights and the kitchen had the basics. The kitchen needs a full sized garage can (with extra trash bags). The...
Wine Lovers Garden Oasis in Sutter Creek!
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

Find out more about New Chicago

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit New Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

The Bonnie Inn Unit 6: You might want to consider this vacation home rental near New Chicago, which is in a shopping district and equipped with air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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 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.