Search Vacation Homes in Equestrian Estates

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Compare 272 Vacation Homes in Equestrian Estates with updated reviews, rates, and availability.

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (73)
"Our party came to town to visit relatives during Christmas holidays. The house was in good working order and met our needs. Beds were comfortable with easy check- in/ check- out."
Furnished Private home in Aurora sleeps 9 guests

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

10.0 out of 10, Exceptional, (2)
"The property was very nice and spacious. The location was great and the parking in the back was amazing. We felt safe and happy our whole stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Discover Wheaton's charm.

9.8 out of 10, Exceptional, (9)
"Larry's property.... I can't even call it a property. It's a HOME!!!! As soon as we walked in, it felt like we were coming to a loved one's house. It was so perfect!!!! We traveled FAR to get there, with our two little girls and our dogs. We were exhausted and overwhelmed after the drive and the Thanksgiving holiday chaos. But walking in, we were immediately so comfortable and cozy. He had towels and cloths set up on the dressers in every room (something I do for my own guests in our own home!)...
Discover Wheaton's charm.

Spanish style home with in-ground pool

9.8 out of 10, Exceptional, (37)
"We really enjoyed the stay! The owner is super responsive and went above and beyond for anything we needed and didn’t have while there. If you will be there for a specific event such as hosting a holiday, make sure to confirm that appliances are available that you might need beforehand. They will make sure you have them! You may want to also bring extra paper towels and toilet paper and toiletries. The TVs are great, and there’s room to get work done. We had a great time here and would...
Spanish style home with in-ground pool

King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

10.0 out of 10, Exceptional, (22)
"I really enjoyed our stay at this location. It had good appliances and was very clean. Owners made it a point to communicate throughout! "
The price is SAR 635
SAR 1,417 total
includes taxes & fees
15 Jan - 16 January 2025
King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (47)
"We stayed here over Thanksgiving week, as none of our families have homes big enough to house us. The property was AMAZING! Very clean, nice little details like snacks and bottled waters in the refrigerator upon arrival. The beds were comfortable, the linens and pillows very nice. Everything was fantastic. We would stay again."
Great place to stay in Warrenville

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

9.8 out of 10, Exceptional, (12)
"We really enjoyed this beautiful home and location for our family trip. The large rooms and open floor plan were perfect for six adults to enjoy. Plenty of local restaurants and shopping nearby. This was also a nice safe neighborhood for evening strolls and we enjoyed the Christmas lights on display."
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Modern Home in Trendy Neighborhood 40 from Downtown Chicago

9.6 out of 10, Exceptional, (12)
"Beautiful nice clean home , nice neighborhood very quiet and safe Host was nice and replied quick! Loved the home will be back !"
Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Big Family Home with 4 King Beds

10.0 out of 10, Exceptional, (1)
"The host did an excellent job of allowing a most pleasurable experience. Syed was very communicative and responsive. The property is just as advertised and we enjoyed ourselves immensely. We will be back!"
The price is SAR 1,075
SAR 2,817 total
includes taxes & fees
29 Dec - 30 Dec
Big Family Home with 4 King Beds

Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

2.0 star property
5.4 out of 10, (3)
"We called and asked was small gatherings allowed and they said yes and they still managed to call police and kick us out "
The price is SAR 770
SAR 1,346 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

5.4 out of 10, (3)
"We really enjoyed our stay here. It's a great area - walking distance to several great restaurant options! Our only frustrations were the lack of toilet paper (2 rolls for 5 people staying for 5 days) and lack of supplies for the oven (cookware only available for stovetop). Other than that, I'd highly recommend staying here. "
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

Feel good, live well in this cozy Wheaton 3 bedroom!

Feel good, live well in this cozy Wheaton 3 bedroom!

Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville

2.0 star property
10.0 out of 10, Exceptional, (3)
"Wow! I cant stress enough how amazing this place is. Tucked away on a cul de sac street and very quiet. The nice quaint aesthetic is so charming. Once stepping inside my family and I were blown away by how clean, spacious and well decorated it was. It was so cozy and comfortable. The kitchen offered everything you may need. We were able to enjoy the spacious backyard and enclosed patio space. The overall location was great since i have family in plainfield and joliet. We absolutely enjoyed our...
Charming 3-bedroom house in fantastic Plainfield, 10 min to Naperville

LUXE 3 BR, 2 BA + Hot Tub

9.0 out of 10, Wonderful, (18)
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The price is SAR 676
SAR 1,316 total
includes taxes & fees
8 Jan - 9 January 2025
LUXE 3 BR, 2 BA + Hot Tub

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (98)
"This Forest Park bungalow was perfect for our ladies weekend. It is clean, comfortable, updated, charming, well stocked with supplies, has off-street parking, and is convenient to the city. I highly recommend this lovely home."
Updated Forest Park 3 BR Bungalow
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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Other property types in Equestrian Estates

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (73)
"Our party came to town to visit relatives during Christmas holidays. The house was in good working order and met our needs. Beds were comfortable with easy check- in/ check- out."
Furnished Private home in Aurora sleeps 9 guests

Cozy 2- bedroom w/ patio mins from Midway Airport

9.8 out of 10, Exceptional, (9)
"The owner definitely pays attention to details. It had towels laid out in these cute little baskets a well stocked kitchen in terms of tools and the decor was very charming. The only reason I didn't give 5 stars is because it is an older building so the water pressure in the shower was low, there's no dishwasher and it is a 2 flat and the upstairs unit controlled the heat and we were on the first floor."
Cozy 2- bedroom w/ patio mins from Midway Airport

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
The price is SAR 504
SAR 923 total
includes taxes & fees
13 Jan - 14 January 2025
Historic Oak Park Residence
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.