Equestrian Estates Holiday Rentals

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Our top choices for Equestrian Estates holiday rentals

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (224)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy

Aparthotel in Harvey

3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is NZ$165
includes taxes & fees
11 Dec - 12 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Apartment in Near West Side

10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Aparthotel in Bridgeport

2.0 star property
The price is NZ$474
includes taxes & fees
23 Dec - 24 Dec
Stylish Apartment near Chicago Downtown

Apartment in East Garfield Park

7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!

Apartment in Blue Island

7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is NZ$599
includes taxes & fees
11 Dec - 12 Dec
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Condo in Austin

9.2 out of 10, Wonderful, (29)
"We were in town with our rowing team for a regatta, and this was a perfect spot to stay! Amenities were perfect for our needs, the living room is super spacious for some morning yoga, and the owners were responsive to any questions we had. Will definitely be saving this location for our trip here next year?"
United States
McKenzie J.
Experience Chicago living near United Center

Holiday Home in Maywood

8.0 out of 10, Very good, (19)
"Very nice place "
United States
Elliot H.
The price is NZ$420
includes taxes & fees
11 Dec - 12 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Apartment in Near West Side

10.0 out of 10, Exceptional, (321)
"Great location, easy check in and out. Wonderful property!"
United States
Lowell M.
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Holiday Home in Shorewood

2.5 star property
The price is NZ$1,081
includes taxes & fees
9 Jan - 10 Jan 2026
Modern 4 Bedroom Private Vacation Home

Condo in Austin

8.6 out of 10, Excellent, (21)
"Stay was perfect. Po"
United States
Maricar P.
Experience Chicago living near United Center

Apartment in Near West Side

9.0 out of 10, Wonderful, (58)
"Roomy well-equiped unit. Location has easy access to the downtown (we used Lyft) and some cool neighborhoods (East Village, ...). "
United States
Adrian S.
Remodeled West Loop Apartment Near United Center

Holiday Home in East Garfield Park

9.0 out of 10, Wonderful, (134)
"Place was very clean, easy drive into the city. "
United States
Scott M.
Luxury Home Away From Your Home

Apartment in Near West Side

8.2 out of 10, Very good, (14)
"Great stay by the United Center "
United States
Brian H.
The price is NZ$367
includes taxes & fees
11 Dec - 12 Dec
Your Perfect 2BR Home

Apartment in Downers Grove

9.6 out of 10, Exceptional, (30)
"The place was super cute and in a great neighborhood. Denise was a great host and was really good with communication. Would recommend!"
United States
Ally W.
The price is NZ$182
includes taxes & fees
11 Dec - 12 Dec
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Mobile Home in Burr Ridge

9.8 out of 10, Exceptional, (34)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is NZ$368
includes taxes & fees
19 Dec - 20 Dec
Less is more! Pet friendly Tiny Home near Chicago!

Apartment in Oak Park

2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home

Holiday Home in Melrose Park

10.0 out of 10, Exceptional, (23)
"Excellent place to stay and host provided great communication. The house is very nice and we also enjoyed the fire pit and hot tub, too! We highly recommend staying at this house and we will be back soon!"
United States
Rich H.
Cozy 3-bedroom house in family-oriented Melrose Park.

Apartment in Oak Park

8.8 out of 10, Excellent, (24)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is NZ$363
includes taxes & fees
11 Dec - 12 Dec
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Condo in Lower West Side

9.4 out of 10, Exceptional, (32)
"Very nice place to stay. Location is close to downtown and the red line. "
United States
Amanda A.
Luxuriant, Foodie, Culture,
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 Equestrian Estates Hotel Reviews

Find out more about Equestrian Estates

Everything you need to know about Equestrian Estates 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 Equestrian Estates 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 Equestrian Estates holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Equestrian Estates holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Equestrian Estates. 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 Equestrian Estates 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 Equestrian Estates holiday rentals we have selected for you start as low as NZ$165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Equestrian Estates rentals

At Expedia, we put the best Equestrian Estates 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 Equestrian Estates 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 Equestrian Estates 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 Equestrian Estates. 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

Are there holiday rentals in Equestrian Estates?

Yes, there are holiday rentals close to the most popular sights in Equestrian Estates, or you can select a more secluded option if you're looking for a relaxing stay. Equestrian Estates is known for its shopping and restaurants.

What are some of the best holiday rentals that Equestrian Estates has to offer?

Modern 4 Bedroom Private Vacation Home : This holiday home rental outside Equestrian Estates offers a BBQ and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What’s there to see and do in Equestrian Estates?

Explore the area and family-friendly sights such as Orland Park Sportsplex, or get out into nature at a spot like Centennial Park. In the wider area, you’ll find Cog Hill Golf & Country Club and Moraine Valley Community College Fine and Performing Arts Center.

What’s a holiday rental in Equestrian Estates like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Equestrian Estates. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.