Equestrian Estates Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Equestrian Estates holiday rentals

Property entrance
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (225)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Desk, laptop workspace, blackout curtains, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Aparthotel in Harvey

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
4.0 out of 10, (68)
"Good "
United States
Abel
The price is HK$658
HK$744 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Apartment in Near West Side

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (270)
"Wonderful place, great location! Communication was easy and everything met and exceeded our expectations."
United States
Kathleen N.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

Stylish Apartment near Chicago Downtown
2.0 star property
Stylish Apartment near Chicago Downtown
Interior
Urban Farm Fun with Goats 10 Minutes To Downtown!

Apartment in East Garfield Park

Urban Farm Fun with Goats 10 Minutes To Downtown!
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!
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very good, (20)
"Very nice place "
United States
Elliot H.
The price is HK$1,156
HK$1,886 total
includes taxes & fees
17 Dec - 18 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center

Condo in Austin

Experience Chicago living near United Center
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
2 bedrooms, WiFi, wheelchair access
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Apartment in Blue Island

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
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 HK$1,149
HK$2,652 total
includes taxes & fees
17 Dec - 18 Dec
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Terrace/patio
Modern 4 Bedroom Private Vacation Home

Holiday Home in Shorewood

Modern 4 Bedroom Private Vacation Home
2.5 star property
The price is HK$3,852
HK$4,857 total
includes taxes & fees
17 Dec - 18 Dec
Modern 4 Bedroom Private Vacation Home
3 bedrooms, iron/ironing board, travel cot, free WiFi
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Apartment in Near West Side

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
10.0 out of 10, Exceptional, (322)
"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
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center

Condo in Austin

Experience Chicago living near United Center
8.6 out of 10, Excellent, (22)
"Stay was perfect. Po"
United States
Maricar P.
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home

Holiday Home in East Garfield Park

Luxury Home Away From Your Home
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
Interior
Less is more! Pet friendly Tiny Home near Chicago!

Mobile Home in Burr Ridge

Less is more! Pet friendly Tiny Home near Chicago!
9.8 out of 10, Exceptional, (34)
"We loved it!!! Perfect space for the 3 of us area is beautiful!! "
United States
Aaliyah G.
The price is HK$805
HK$1,628 total
includes taxes & fees
21 Dec - 22 Dec
Less is more! Pet friendly Tiny Home near Chicago!
Fridge, microwave, oven, stovetop
Your Perfect 2BR Home

Apartment in Near West Side

Your Perfect 2BR Home
8.2 out of 10, Very good, (14)
"Great stay by the United Center "
United States
Brian H.
The price is HK$576
HK$1,586 total
includes taxes & fees
5 Jan - 6 Jan 2026
Your Perfect 2BR Home
Property grounds
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Apartment in Downers Grove

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
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 HK$469
HK$868 total
includes taxes & fees
18 Dec - 19 Dec
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Exterior
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Holiday Home in Greater Grand Crossing

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
8.4 out of 10, Very good, (12)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
United States
Tenika P.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Interior
Historic Oak Park Home

Apartment in Oak Park

Historic Oak Park Home
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
The price is HK$1,204
HK$2,242 total
includes taxes & fees
17 Dec - 18 Dec
Historic Oak Park Home
Property grounds
Cozy 3-bedroom house in family-oriented Melrose Park.

Holiday Home in Melrose Park

Cozy 3-bedroom house in family-oriented 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.
Smart TV
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Apartment in Berwyn

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
9.6 out of 10, Exceptional, (29)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Fridge, microwave, oven, stovetop
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Apartment in Oak Park

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
8.8 out of 10, Excellent, (25)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is HK$552
HK$1,629 total
includes taxes & fees
17 Dec - 18 Dec
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
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

Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

10/10 Excellent
"The front desk agent was very professional and efficient. She got me registered well under ten minutes and shared information about the hotel’s amenities & complimentary meals. The agent also accommodated my request to stay on a lower level floor. The room was clean and close to the elevators. The bed was very comfortable!"
Janice 2-night trip
Posted 1 day ago
Embassy Suites by Hilton Chicago Lombard Oak Brook

Find out more about Equestrian Estates

Search for holiday rentals in Equestrian Estates on Expedia! You can easily find your home rentals, villas, holiday apartments in Equestrian Estates using one of the methods below:

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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 of 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.