Addison Vacation Rentals

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Browse Select Addison Vacation Homes

Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
10.0 out of 10, Exceptional, (11)
"The listing did not disappoint for our group of frienda reunighring for a 2 night event. It's just as described & more! Great location, the patio is such a bonus, Dan the host was amazing at communicating before & after, and that patio 😍 Thak you- we hope to he back soon! soon!"
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.8 out of 10, Exceptional, (77)
"Property was clean, manager was very easy to communicate with, lots of spacious beds / bathrooms, parking was easy and kitchen and living space included everything we needed. Location near Wells Street, North Avenue, Lakefront and Brown Line was perfect. Everything was easily walkable. This was a great house in the middle of a nice neighborhood for a large group."
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Luxury SOHO Styled Two-Level Townhouse - Old Town
10.0 out of 10, Exceptional, (10)
"We had a great stay at this property. It is walking distance from everything you need in old town but also safe, quiet, and secure! Would highly recommend to other groups looking for a weekend in Old Town Chicago!"
Luxury SOHO Styled Two-Level Townhouse - Old Town
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
9.0 out of 10, Wonderful, (7)
"Great place to stay for a work conference at Sheraton. For three people it was much cheaper than the hotel."
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (114)
"Definitely gently used but was comfortable. Ms. Linnie, the host, is very responsive and accommodating. Was missing hair dryers and flat sheets on beds but did not negatively affect our visit."
Luxury Home Away From Your Home
Furnished Private home in Aurora
9.4 out of 10, Exceptional, (65)
"We stayed at this house for a few days in Aurora visiting family. The house was exactly as listed! Lots of rooms for sleeping and “spreading out”. Excellent place to stay and will rebook in future! I definitely recommend this listing!!"
Furnished Private home in Aurora
Fox River Retreat
9.8 out of 10, Exceptional, (16)
"Very nice, clean roomy home. Would be great for family stay. Convenient to downtown St Charles and S. Elgin. Family that came over were very impressed."
Fox River Retreat
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (39)
"Great yard. Good area."
Breathtaking home close to Schaumburg, Chicago
Des Plaines Vacation Rental w/ Spacious Backyard!
8.4 out of 10, Very good, (5)
"The house was small, but perfect for us 3 girls for a weekend. The back deck was excellent! The driveway was a bit difficult to find…you have to go around the corner and down an alley, but it was nice to have off-street parking. Overall, the house was great, the neighborhood was quiet, and we had a fantastic weekend!"
Des Plaines Vacation Rental w/ Spacious Backyard!
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
2.0 star property
9.4 out of 10, Exceptional, (3)
"Comfortable beds, parking good, clean and cute decor!"
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Beautiful, Remodeled Penthouse Unit in Old Town!
9.2 out of 10, Wonderful, (14)
"This family trip works perfectly for our 12 family members. The location was great in old town and close to beach and other good places. We only wanted a mirror outside the bathroom so we do not have to wait for someone getting out of the bathroom just fto use the mirror. Otherwise everything was good."
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (28)
"Back to Chicago with a group for a work trip and of course we went back to the place we stayed at last time. Once you find a gem like this one, you stay with it! They keep this place with all the amenities you’d have at home. It’s incredibly spacious and the parking spots make it deal for a group. We’ll be back!! Jon"
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Your Next Vacation Home
9.8 out of 10, Exceptional, (23)
"Good location to Rosemont. "
The price is CA $231
CA $421 total
includes taxes & fees
Sep 22 - Sep 23
Your Next Vacation Home
Oak Park, IL, entire house, short walk to train.
9.4 out of 10, Exceptional, (19)
"Great host communicates well if you need him. Helped with all my concerns. Check in was was easy and smooth. Property inside and out was also clean and in a nice neighborhood with access to ALOT. Thank you"
Oak Park, IL, entire house, short walk to train.
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
10.0 out of 10, Exceptional, (19)
"Beautiful, spacious, light-filled carraige house in a gorgeous historical neighborhood. Close to beach, shops, cafes. Janet was very accommodating and very hospitable. We loved it!"
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
9.2 out of 10, Wonderful, (10)
"The property was nicely furnished and had all of the basic necessities. It was clean and smelled fresh. There was a welcome sign on the kitchen island but not very many details/rules so we weren't sure where to leave the used linens upon .Overall, the house was very nice.departure."
The price is CA $298
CA $585 total
includes taxes & fees
Oct 21 - Oct 22
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Stunning Condo #2 - Downtown River North!!!
9.4 out of 10, Exceptional, (10)
"Looks just like the pictures, the house was very clean and decorated so cute! The host was very easy to get in touch with if needed. Amazing stay!! "
Stunning Condo #2 - Downtown River North!!!
5 BR / 3.5 BA Newly Built Home in Logan Square!
7.6 out of 10, Good, (7)
"We had a minor hiccup in the beginning and Sandy got it taken care of within an Hour. Overall great stay"
5 BR / 3.5 BA Newly Built Home in Logan Square!
- Fully-Equipped Condo - King Bed - Massive yard -
10.0 out of 10, Exceptional, (16)
"As good as the pictures on VRBO are of this site, they don't quite capture the charming character of this house. And it is a house (the lower floor), an absolute classic from the late 1800s. Beautifully and thoughtfully appointed in all regards. Main living areas, kitchen, bathrooms - all excellent. The bedding is top notch (love those pillows). The deck is a great place for coffee in the AM, or wine in the afternoon. The owner is super responsive and helpful. Location is super...
The price is CA $237
CA $474 total
includes taxes & fees
Oct 20 - Oct 21
- Fully-Equipped Condo - King Bed - Massive yard -
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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 Addison

WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (220)
"Mucho olor a marihuana, y que no limpian las habitaciónes solo si pagas adicional y allí dice que cada 14 días limpian y solo es si pagas debería ser un derecho por estar alojado allí por lo menos una vez a la semana no te dan cambio de sábanas ni toallas "
The price is CA $122
CA $129 total
includes taxes & fees
Sep 29 - Sep 30
WoodSpring Suites Chicago Addison
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (543)
"Wonderful place "
The price is CA $206
CA $282 total
includes taxes & fees
Sep 30 - Oct 1
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (370)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is CA $269
CA $316 total
includes taxes & fees
Oct 21 - Oct 22
Sonder South Wabash
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.