Designer Home | Steps to the Obama Center & Beach | House in Chicago
5 Bedroom House in Woodlawn, Chicago
Experience Chicago's most distinctive designer retreat. The Dorchester blends grand Victorian architecture with magazine-worthy interiors, featuring dramatic entertaining spaces, bespoke design details, and a chef's kitchen designed for gathering. Crafted for guests who appreciate exceptional homes, this private residence delivers a stay that's as memorable as the city itself.
Stay here. Communication is sharp, support is discreet, and everything just works.
We don’t hover—you get the space to own your stay. Check-in is fully automated, and your privacy is the priority. When you need us, we’re a text away for anything from elite car services to hard-to-get reservations in Wrigleyville and North Halsted. Otherwise, the space is yours. No friction. No noise. Just your stay, exactly how it should be.
Access is seamless, private, and fully controlled.
You’ll have exclusive use of the entire 5 BR home including five bedrooms, 3.5 bathroom, a full kitchen, and a comfortable living area designed for both relaxation and entertainment.
Entry is keyless with a unique access code provided before arrival, allowing for frictionless self check-in at any time. Your code is active for the duration of your stay, ensuring both convenience and security.
On-site shared laundry is available for guest use, and 2 spaces inside of our onsite parking garage.
Everything is designed for privacy, ease, and an elevated stay from the moment you arrive.
The Dorchester offers multiple gathering spaces thoughtfully designed for both entertaining and relaxing. The home features a formal sitting room, designer living room, chef's kitchen, dining room, and several cozy lounge areas throughout the property.
Sleeping Arrangements:
• Bedroom 1: King Bed + Smart TV + Ensuite Master Bath with soaking tub and standing shower.
• Bedroom 2: King Bed + Smart TV
• Bedroom 3: Queen Bed + Smart TV + Ensuite Bathroom with soaking tub.
• Bedroom 4: Queen Bed + Smart TV
• Bedroom 5: Two Twin-Over-Twin Bunk Beds (Sleeps 4) + Smart TV
The chef's kitchen features premium appliances, generous counter space, and seating for gathering over meals and conversation. Throughout the home, guests will find bold designer interiors, curated artwork, historic architectural details, and comfortable spaces to unwind.
Additional amenities include private garage parking, high-speed Wi-Fi, Smart TVs in every bedroom, and ample space for families, groups, graduation weekends, executive retreats, and extended stays.
We’re excited to host you and want to ensure your stay is comfortable, enjoyable, and stress-free. To help make that happen, please review the rules below.
General Rules
No Smoking Indoors: Smoking and vaping are strictly prohibited inside the property. Outdoor smoking is permitted in designated areas. Violations will result in a $500 fine.
No Parties or Events: Parties, events, or unregistered overnight guests are not allowed. Violations may result in immediate cancellation and fines of up to $750.
Quiet Hours: 10:00 PM – 7:00 AM. Three verified noise complaints from neighbors may result in a $300 fine.
Check-In & Check-Out
Check-In: Begins at 4:00 PM. Early check-in before 2:00 PM may be available with approval and rush cleaning fee.
Check-Out: 10:00 AM. Late check-outs require prior approval; unapproved late check-outs may incur a full-night charge.
Damage & Maintenance
Please report any cleaning concerns, damages, or issues within 24 hours of arrival. Prompt reporting allows us to resolve issues quickly. Failure to report may result in fees if damages are later found.
Designer Home | Steps to the Obama Center & Beach is located in Woodlawn. Designer Home | Steps to the Obama Center & Beach provides accommodation, featuring Air Conditioner, Balcony/Terrace, Security/Safety, among other amenities. This House features Air Conditioner, Parking and TV to make your stay a comfortable one.
Designer Home | Steps to the Obama Center & Beach has 5 Bedrooms , 3 Bathrooms, and max occupancy of 12 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Woodlawn has interesting places to visit. If you want to learn more about the House in Woodlawn, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Air conditioning
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Heating
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3+ bathrooms
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Hair dryer
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5 bedrooms
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Bed sheets provided
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Dining table
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Fireplace
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Oven
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Coffee/tea maker
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Refrigerator
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Microwave
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Toaster
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Dishwasher
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Cookware/dishes/utensils
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Stovetop
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Washing machine and dryer
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Onsite parking
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Electric car charging station on site
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No pets allowed
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Smoke-free property
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Games
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TV
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Unit size: 4000 sq ft (372 sq m)
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Office
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Travel crib
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Children's books
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Iron/ironing board
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Free WiFi
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Barbecue grill
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Deck or patio
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Garden
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Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
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Fire extinguisher
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First aid kit
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Smoke detector installed (host has indicated there is a smoke detector on the property)
Policies
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number r25000133236, 60637 safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
FAQ's
Is this property pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the property have a swimming pool?
No, this Woodlawn house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in property?
Best-rates for the Woodlawn house starts from $1,261 per night with includes Air Conditioner, Balcony/Terrace, Security/Safety, Parking, TV, Child Friendly, Kitchen, Sports/Activities, Wellness Facilities, Fireplace, Barbecue/Outdoor Cooking, Internet, Laundry, Entertainment, Heating with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is property a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the property wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Woodlawn house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the property?
Based on the information reported by the owner or manager, the Woodlawn house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for property?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
