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:: The Wolcott :: Modern Elegance at Its Finest

Photo gallery for :: The Wolcott :: Modern Elegance at Its Finest

Exterior
Lobby
Living area
Interior
Living area

Reviews

9.4 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade and game room.
  • Discover nearby landmarks
    Walk to Milwaukee Avenue
4 bedrooms5+ bathroomsSleeps 12

Popular amenities

  • Spa pool on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Chicago, IL
  • Place, Milwaukee Avenue
    ‪2 min walk‬
  • Place, Wood Street Gallery
    ‪3 min walk‬
  • Place, The Salt Shed
    ‪2 min drive‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪30 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

5 bathrooms, 2 half bathrooms

Bathroom 1

Toilet

Bathroom 2

Towels provided · Bathtub or shower

Bathroom 3

Towels provided · Bathtub or shower

Bathroom 4

Towels provided · Bathtub or shower

Bathroom 5

Toilet

Bathroom 6

Towels provided · Bathtub or shower

Bathroom 7

Towels provided · Bathtub or shower

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

:: The Wolcott :: Modern Elegance at Its Finest


The Wolcott is a 6000 sq-ft, multi-level modern-contemporary masterpiece home with 4 fully-suited bedrooms, plus additional room space to easily accommodate additional sleeping guests comfortably in king and queen air mattresses (and linens) provided.

ATTENTION GAMERS: The Wolcott features whole house indoor and outdoor Orby mesh wifi system - with FIBEROPTIC 1.5 Gps broadband connection.

5 Full Bathrooms and two 1/2 baths. 800 sq ft private (fenced) backyard leading from a 360 sq ft bluestone patio (located off great room), private car garage and carport, roof-top decks including unobstructed 360 degree view as well as skyline view of Chicago's downtown, Exercise Room on the 2nd floor (can easily accomodate king and queen air mattresses provided), custom wine cellar, pool table. Phenomenal hosting space with whole-house audio, Custom Kitchen with 44 sq ft marble center island, Bosch and Thermador appliances, two Thermador dishwashers. The Wolcott is an exceptional property and we welcome the opportunity to host you and help to create a memorable and comfortable stay for you and your guests.

PLEASE NOTE: Events are allowed: HOWEVER, events such as larger parties (ie; more than 25 guests), weddings, rehearsal dinners, family reunions, etc will be subject to additional pricing depending on # of guests and scope of your event.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
Events will be considered on a case by case basis.
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas
NO LOUD OUTDOOR MUSIC OR NOISE AFTER 11pm

Important information

You need to know

Property Registration Number 60622, R24000119085
Property # 2388004vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 75
Note from host: Events will be considered on a case by case basis.
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Chicago

West Town, a neighbourhood in Chicago, is home to this holiday home. Merchandise Mart and Cloud Gate are notable landmarks, and travellers looking to shop may want to visit Michigan Avenue and Navy Pier. Travelling with kids? Don't miss Lincoln Park Zoo and Field Museum of Natural History. Take the opportunity to explore the area for water adventures such as power boating and other activities like winery tours.
View more Holiday homes in ChicagoOpens in a new window
Map
Chicago, IL

What's nearby

  • Milwaukee Avenue - 2 min walk - 0.2 km
  • Wood Street Gallery - 3 min walk - 0.3 km
  • House Theatre - 10 min walk - 0.9 km
  • The 606 - 12 min walk - 1.1 km
  • The Salt Shed - 2 min drive - 1.5 km

Getting around

  • Chicago Clybourn Station - 2 min drive
  • Damen Station - 8 min walk
  • Chicago Midway Airport (MDW) - 34 min drive

Restaurants

  • ‪The Standard Bar & Grill - ‬6 min walk
  • ‪Colectivo Coffee Wicker Park - ‬5 min walk
  • ‪Parlor Pizza Bar - ‬4 min walk
  • ‪Devil Dawgs Wicker Park - ‬5 min walk
  • ‪The Wormhole Coffee - ‬6 min walk

Frequently asked questions

Is :: The Wolcott :: Modern Elegance at Its Finest pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at :: The Wolcott :: Modern Elegance at Its Finest?

As of 26 June 2026, prices found for a 1-night stay for 2 adults at :: The Wolcott :: Modern Elegance at Its Finest on 6 July 2026 start from AU$4,706, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at :: The Wolcott :: Modern Elegance at Its Finest?

On-site parking is available at the property.

What time is check-in at :: The Wolcott :: Modern Elegance at Its Finest?

Check-in begins at 4:00 PM.

What time is check-out at :: The Wolcott :: Modern Elegance at Its Finest?

Checkout is at 11:00 AM.

Where is :: The Wolcott :: Modern Elegance at Its Finest located?

This family-friendly Chicago holiday home is located in West Town, within 1 mi (2 km) of Milwaukee Avenue, Humboldt Park and The Salt Shed. United Center and Michigan Avenue are also within 3 miles (5 km). Damen Station is 8 minutes by foot and Division Station is 9 minutes.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 1 out of 16 reviews

9.0/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

9.8/10

Location

8.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Paul W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House is very cool. Host was friendly and helpful. The house was a hit with my vacation group and made for a very fun weekend.
Stayed 2 nights in Jun 2026
Verified

10/10 Excellent

Tom W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing house. An entertainers dream. We were able to host an indoor/outdoor engagement party and every guest commented on how much they liked the house. So many different areas to hang out. We spent most of the time in the kitchen, living room and outdoor patio.
Stayed 2 nights in Jun 2026
Verified

10/10 Excellent

Carl A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friendly and thorough host. Beautiful and nicely equipped house.
Stayed 5 nights in Nov 2025
Verified

10/10 Excellent

Clara M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

Great property with perfect location. Property owner extremely responsive!
Stayed 4 nights in Oct 2023
Verified

10/10 Excellent

Suzanne R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house!!!

This house was so beautiful! From the bottom level to the amazing view on the top everything was perfect!
Stayed 4 nights in Nov 2023
Response from VrboOwner on 28 Nov 2023
Thanks so much, Suzanne :)
Verified

10/10 Excellent

Kathryn T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!!!

Matt is the absolute best host and was phenomenal to work with leading up to our stay!! The house was beautiful and the perfect place for us to stay. Highly recommend!!
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Anne Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay at the Wolcott

The Wolcott is very beautiful, and even more impressive than the listing showed. Matt was very communicative when we had questions about the house. There was plenty of room for my friends and me to stay, and throw a birthday party. Would definitely stay again!
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Lilia G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Wedding Weekend at the Wolcott

We hosted about 55 guests at the Wolcott for our wedding ceremony. Everyone had such a wonderful time and complimented how beautiful Matt’s home was. There was so much room to have our guests inside and out. Matt was very communicative from when we booked our stay up until after our guests left. Definitely the place to stay if you would like to host any event big or small.
Stayed 3 nights in May 2023
Response from VrboOwner on 27 June 2023
Thank you Lilia. You and Tyler had an epic wedding! Truly a pleasure meeting both of you. You are awesome people.
Verified

10/10 Excellent

Hurube S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer Time Chi

This home is Amazing!! We were there for the hottest weekend in Chicago so it was hot in the common area and the top level. It was clean for the most part but a little too much dog hair on the beddings and stairs.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Theo L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Top of The Line!

This place has so much charm that we had to book it again. The second time around was just as pleasing as the first... Our group loves this home and the many features inside. The neighborhood is friendly. The owner is always responsive. The area is safe and minutes away from downtown Chicago. Looking forward to next years stay because this home is our first and only choice when in Chicago! Special thanks to the owner for trusting us with your home.
Stayed 3 nights in Nov 2022
Response from VrboOwner on 27 June 2023
Your group was a real pleasure to have in my home, Theo. Thank you for your excellent communication, for leaving my home in such great condition and for being a good guy in general. Come back anytime!
Verified

10/10 Excellent

Karen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful weekend at The Wolcott

The house is beautiful with many areas both indoors and outdoors for entertaining and relaxing. Matt was very responsive and accommodating as the home owner. As a bonus, it is within easy walking distance of key locations in Wicker Park. The house has four suited bedrooms, several other spaces that can be used for sleeping on inflatable mattresses, an extra full bath and a powder room. Our multiple families fit successfully and we stayed at the house a majority of the time. We hosted a two-year-old birthday party and all attendees, young and old, had a great time.
Stayed 2 nights in Aug 2022
Verified

10/10 Excellent

Sterling G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Home & Location

Matt’s place, The Wolcott, is a fantastic short-term rental. You can tell it’s a full-time residence normally, but that doesn’t stop it from being quite the accommodation. It’s absolutely HUGE with everything you could need. Matt did a good job communicating a few days prior to check-in day to make sure things were set. Instructions were detailed - took a lot of guess work out of everything. Furnishing and spaces are aplenty so for whatever the occasion calls for, you’ll have an appropriate space to enjoy it at. Definitely make sure to check out the rooftop views immediately upon arrival!
Stayed 3 nights in Aug 2023
Response from VrboOwner on 10 Aug 2023
Thanks so much, Sterling. You are welcome back anytime. It was a pleasure. - Matt
Verified

10/10 Excellent

Lori H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous!

Our family of 12 were very comfortable in this amazing home! We had a surprise 60th for my husband with approx 30 people. It was perfect for entertaining. There are multiple levels to enjoy and the outside patio areas are fun and inviting. The views from the rooftop are nothing short of amazing! The house is equipped nicely with anything you need and the beds are comfortable. Communication with Matt was quick and he was very accommodating with our special requests. We would definitely rent here again! It made our surprise even more special!
Stayed 2 nights in Aug 2022
Verified

8/10 Good

Calvin Y.

Liked: Check-in, communication, location

Entertainment Supreme

The home was built to entertain. It has all that you could imagine that you would need to host a party of up to 50 people. Firepit, pool table, entertainment room with large screen TV, wine cellar the works. In a great neighborhood surrounded by everything you could need or imagine. Fantastic views from the upper roof top balcony. The home is large so it took time to find everything and learn all the gadgets, including the steam shower in the master bathroom. It also serves as the host's primary residence, therefore you had to share refrigerator space. Number of bedrooms and beds did not jive with the listing, but we worked through it. The host was accommodating. We enjoyed it to the max and my wife's birthday party was a great success.
Stayed 2 nights in Jul 2022
Verified

2/10 Terrible

Kathleen H.

Liked: Communication
Disliked: Cleanliness, check-in, listing accuracy

Stay away

The house smelled when we stalked in. All garbages we’re full . Refrigerator was full with food. Couldn’t fit any of ours food in.. and so was the freezer. There weren’t towels in the every bathroom. The 2nd floor wouldn’t cool below 80. The hvac is terrible. The dog walker opened front door with key unannounced. Cat hair all over bed sheets. Didn’t feel clean. The owner lives here full time and has all of his things around the house. Couldn’t even use master bedroom closet bc it was full with his clothes. Not kid friendly either. Random pills found in bathroom drawers.
Stayed 10 nights in Jun 2022
Verified

10/10 Excellent

Aham O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unbelievable entertainment house. Gorgeous!!

This is a beautiful property. Aesthetics are impeccable. Televisions everywhere. An entertainment spot. Great location as well. The only drawback is that some of the bedrooms are small.
Stayed 6 nights in Mar 2022

About the host

Hosted by Matthew

Host profile image

Languages:

English
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