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Holiday Homes in Far Southwest Side

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Far Southwest Side

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

6.6 out of 10, (4)
"Very nice place "
The price is NZ$407
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"Very communicative and good host for sure!"
The price is NZ$562
includes taxes & fees
19 Aug - 20 Aug
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (51)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.6 out of 10, Exceptional, (32)
"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "
Cozy Home Sweet Homewood.
Vintage Urban Retreat
Exterior detail

Vintage Urban Retreat

10.0 out of 10, Exceptional, (9)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is NZ$847
includes taxes & fees
20 Aug - 21 Aug
Vintage Urban Retreat
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel cot

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

2.0 out of 10, (1)
"When I booked this property it was the intention to have a joyful time with my family for an extended family event. We were unable to access the property the day of causing me to spend an extra 600 for us to stay at another hotel after spending 2 hours on the phone with customer service. To top it off we were harassed by the next door neighbor who attempted to take pictures of our vehicle and report to us that this property was considered an illegal listing. Once we gained entry the property was...
The price is NZ$1,623
includes taxes & fees
19 Aug - 20 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (11)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Cozy 3-bedroom house in family-oriented Melrose Park.
Property grounds

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (20)
"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "
Cozy 3-bedroom house in family-oriented Melrose Park.
Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

6.8 out of 10, (8)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Cheerful 3 bedroom. Feels like home.
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom. Feels like home.

3.5 star property
9.8 out of 10, Exceptional, (10)
"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"
Cheerful 3 bedroom. Feels like home.
New home w/view & party deck - 2nd Floor
Fridge, microwave, oven, stovetop

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (22)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Fridge, microwave, oven, stovetop

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (13)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
The price is NZ$901
includes taxes & fees
2 Sept - 3 Sept
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (5)
The price is NZ$931
includes taxes & fees
2 Sept - 3 Sept
4BR Retreat w/ Theater, Game Room & Backyard
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is NZ$1,109
includes taxes & fees
18 Aug - 19 Aug
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Lincoln Park Living - Suite 1
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (30)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1
Lincoln Park Living - Suite 2!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (42)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Fridge, microwave, oven, stovetop

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

10.0 out of 10, Exceptional, (88)
"Well-equipped kitchen, comfortable beds, easy parking and very clean. A perfect place to stay for our short trip to Chicago. "
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Fridge, microwave, oven, stovetop

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

9.2 out of 10, Wonderful, (15)
"The house was very nice. Great neighborhood."
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
2BR Traveler's Favorite, Modern and Clean
Desk, iron/ironing board, travel cot, free WiFi

2BR Traveler's Favorite, Modern and Clean

The price is NZ$617
includes taxes & fees
19 Aug - 20 Aug
2BR Traveler's Favorite, Modern and Clean
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 Far Southwest Side Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Loved staying at this hotel! This was our second time and we enjoyed it. Super easy to get everywhere and can walk downtown. Would definitely stay here again"
Jacqueline 3-night trip
Posted 22 hours ago
The Wade