Entire home

:: The Wolcott :: Modern Elegance at Its Finest

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

A modern staircase with metal railings and wooden steps, leading to an upper level.
A spacious kitchen with white cabinetry, a central island, stainless steel appliances, and a modern pendant light fixture.
A spacious living area with a staircase, a fireplace, and a flat-screen TV mounted on a wooden wall.
A spacious living room with a large window, a fireplace, and a kitchen in the background.
A modern living room with a sectional sofa, a leather armchair, and a flat-screen TV mounted on the wall.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Discover nearby landmarks
    Walk to Milwaukee Avenue

Popular amenities

  • Balcony or patio
  • Hot tub on site
  • On-site fitness centre
  • Arcade/game room
  • Barbecue grill
  • Air-conditioning

Explore the area

View in a map
Chicago, IL
  • Place, Milwaukee Avenue
    ‪2 min walk‬
  • Place, The Den Theatre
    ‪5 min walk‬
  • Place, The 606
    ‪12 min walk‬
  • 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

Add dates for prices

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About the area

Chicago

West Town, a neighbourhood in Chicago, is home to this holiday home. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Millennium Park and Grant Park. Looking to enjoy an event or a game? See what's going on at United Center or Wrigley Field. Take the opportunity to explore the area for water adventures such as power boating and other activities like winery tours.
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Map
Chicago, IL

What's nearby

  • Milwaukee Avenue - 2 min walk - 0.2 km
  • The Den Theatre - 5 min walk - 0.5 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

  • ‪Parlor Pizza Bar - ‬4 min walk
  • ‪The Wormhole Coffee - ‬6 min walk
  • ‪Devil Dawgs Wicker Park - ‬5 min walk
  • ‪Colectivo Coffee Wicker Park - ‬5 min walk
  • ‪Taco Bell - ‬5 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 24 Oct 2026, prices found for a 1-night stay for 2 adults at :: The Wolcott :: Modern Elegance at Its Finest on 3 Nov 2026 start from £5,005, 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 Chicago Riverwalk 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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 Jun 2023
Thank you Lilia. You and Tyler had an epic wedding! Truly a pleasure meeting both of you. You are awesome people.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 Jun 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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

2/10 Terrible

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 review

10/10 Excellent

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
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