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Our top choices for Equestrian Estates holiday rentals

Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
5.6 out of 10, (4 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
The price is £421
includes taxes & fees
9 Jun - 10 Jun
Group-Friendly 4BR Hyde Park Retreat Near UChicago

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown

Dog-Friendly Apt w/ Yard: 10 Mi to Downtown
Woodlawn
10.0 out of 10, Exceptional, (1 review)
"Great host very accommodating."
United States
Kali P.
The price is £247
includes taxes & fees
9 Jun - 10 Jun
Dog-Friendly Apt w/ Yard: 10 Mi to Downtown

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
10.0 out of 10, Exceptional, (6 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
The price is £208
includes taxes & fees
23 Jun - 24 Jun
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
10.0 out of 10, Exceptional, (1 review)
"Very clean..out side garbage needs to be picked up. Toilet seats were loose and under kitchen sink was wet. Could use a toaster and some basic condiments. "
United States
margaret
The price is £362
includes taxes & fees
9 Jun - 10 Jun
Modern Stylish Comfort Near Casino and Hwy

5 Mins to Downtown CHI Sleeps 10 - Parking + Games

5 Mins to Downtown CHI Sleeps 10 - Parking + Games
Lower West Side
10.0 out of 10, Exceptional, (3 reviews)
"We loved the location, the area is awesome! Great stay, highly recommend. "
United States
Db D.
The price is £304
includes taxes & fees
8 Jun - 9 Jun
5 Mins to Downtown CHI Sleeps 10 - Parking + Games

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
8.0 out of 10, Very good, (6 reviews)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is £249
includes taxes & fees
8 Jun - 9 Jun
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
The price is £217
includes taxes & fees
9 Jun - 10 Jun
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is £244
includes taxes & fees
30 Jun - 1 Jul
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Cozy Chic Retreat Near Downtown - Sleeps 7

Cozy Chic Retreat Near Downtown - Sleeps 7
Lawndale
Cozy Chic Retreat Near Downtown - Sleeps 7

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Lawndale
8.8 out of 10, Excellent, (3 reviews)
"Great stay, perfect for our group of 6, everyone had there own room! Necessities right around the corner if needed Cermack rd a few feet away, gets you about everywhere! We wanted a real life Chicago experience, and it was great. Owner very responsive! Permit on street parking pretty accessible most times. Definitely will stay again!"
United States
Beth
The price is £333
includes taxes & fees
18 Jun - 19 Jun
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Luxurious, Cozy Beauty 10 min from Downtown Chicago

Luxurious, Cozy Beauty 10 min from Downtown Chicago
Lawndale
8.6 out of 10, Excellent, (9 reviews)
"Close to public transport, clean, helpful host"
United States
Aaron W.
The price is £175
includes taxes & fees
17 Jun - 18 Jun
Luxurious, Cozy Beauty 10 min from Downtown Chicago

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
Lower West Side
The price is £305
includes taxes & fees
17 Jun - 18 Jun
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10

Modern Pilsen Apt 3 Bedrooms

Modern Pilsen Apt 3 Bedrooms
Lower West Side
5.0 out of 10, (2 reviews)
"Everything was wonderful except the bathroom. When we checked in there was quite a bit of hair on the floor of the bathroom and in the tub. Everything else was very clean. Beds comfortable. Water pressure good. Felt safe in the area. Hard to find a parking spot Friday night. The kids had fun with all the games. "
United States
Naomi D.
The price is £302
includes taxes & fees
17 Jun - 18 Jun
Modern Pilsen Apt 3 Bedrooms

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (24 reviews)
"The host was great and communication for her to respond was great. The amenities were good as well"
United States
Shantel U.
The price is £335
includes taxes & fees
8 Jun - 9 Jun
Spacious 3br home near Chicago, fenced yard for pets

Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.4 out of 10, Exceptional, (6 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
Newly Remodeled Gem | Heart of Chicago

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
The price is £476
includes taxes & fees
14 Jun - 15 Jun
Game Room • Fire-pit • Playground • Gym • Billiard

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
The price is £132
includes taxes & fees
8 Jun - 9 Jun
Soothing 1 bedroom apartment with AC in charming Oak Lawn,

3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is £484
includes taxes & fees
8 Jun - 9 Jun
3-bedroom house in lovely Matteson with cool AC breeze

Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is £662
includes taxes & fees
9 Jun - 10 Jun
Sleeps 18 • 7BR • Gym • Game Room • Theater
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, apart-hotels, 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 £66 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Equestrian Estates offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.