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The Dorchester Designer Retreat - Chicago, Illinois
The Dorchester Designer Retreat - Chicago, Illinois
The Dorchester Designer Retreat - Chicago, Illinois
The Dorchester Designer Retreat - Chicago, Illinois

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The Dorchester Designer Retreat

3-9 Keys3-9 Keys5 Bedrooms10 Guests3 BathsView Amenities

Description

The Dorchester Designer Retreat

Highlights
• Near Hyde Park and Obama Presidential Center

• Grand Victorian architecture with designer interiors

• Private backyard with fire pit dining

Set within Chicago's historic South Side, The Dorchester offers a distinctive residential experience where classic Victorian architecture meets contemporary design. Created for travelers who appreciate character, scale, and thoughtful craftsmanship, this private residence balances the elegance of a historic home with the comfort and functionality expected of a modern luxury stay. Positioned near Hyde Park's cultural institutions, university community, and lakefront attractions, it serves as a refined base for exploring one of Chicago's most dynamic neighborhoods.

Inside, a collection of beautifully appointed living spaces encourages both connection and retreat. Formal and casual gathering rooms create a natural rhythm throughout the home, while curated artwork, rich color palettes, and architectural details lend a sense of personality rarely found in traditional accommodations. At the heart of the residence, the chef's kitchen features premium appliances, generous preparation space, and inviting seating designed for shared meals, conversation, and memorable evenings together.

The home's accommodations are thoughtfully arranged to provide both privacy and comfort. The primary suite features a king bed, Smart TV, and an ensuite bath complete with a soaking tub and separate shower. Additional king and queen bedrooms offer stylish, restful environments, while the bunk room provides flexible accommodations for families and groups. Throughout the residence, layered textures, carefully selected furnishings, and abundant natural light create an atmosphere that feels both elevated and welcoming.

Outdoor living extends the home's appeal beyond its interiors. A private fenced backyard provides space to gather beneath the open sky, with outdoor dining, comfortable seating, a fire pit, and grilling amenities creating opportunities for relaxed afternoons and evening conversations. Practical luxuries including garage parking, EV charging capability, high-speed Wi-Fi, dedicated workspaces, and laundry facilities further enhance the experience for both short visits and extended stays.

Whether visiting for a university event, a family gathering, an executive retreat, or a city escape, The Dorchester places guests within reach of many of Chicago's most significant cultural destinations. Days may include exploring Hyde Park, discovering museums and lakefront parks, or venturing farther afield to Indiana Dunes National Park before returning to a residence that feels both inspiring and deeply comfortable. The result is a stay defined not simply by where you sleep, but by the character, design, and sense of place that surround every moment.


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Property Amenities

No Pets Allowed | Not Handicap Accessible

Entertainment
40"+ TV
Streaming Service(s)
Facilities
Chef’s Kitchen
Dedicated Work Space
Office
Other
Air Conditioning
Fireplace
Washer & Dryer
Wireless Internet
Outdoor
Firepit
Outdoor Grill
Outdoor Lounge



Property Details

Size

Private Residence with 3 Levels
5 Bedrooms, 3 Baths, 1 Half bath, 3100 square feet, 288 square meters

Bedrooms

King, King, Queen, Queen, and 2x Bunk
10 Guests maximum

Nearest airport

Chicago Midway International Airport (MDW)
30 minutes by car

Property View

Historic residential streetscape

Activities of Interest

  • Arts
  • Golf
  • Shopping
  • Watersports
  • Explore exhibits at the Museum of Science and Industry
  • Visit the DuSable Black History Museum
  • Discover galleries at the Smart Museum of Art
  • Play golf at Jackson Park Golf Course
  • Shop local retailers along 53rd Street
  • Kayak or paddle on Lake Michigan

Places of Interest

  • Obama Presidential Center & Jackson Park – Future presidential center and historic lakefront park
  • University of Chicago – Prestigious campus known for architecture and culture
  • Museum of Science and Industry – Interactive exhibits in a landmark museum
  • Promontory Point – Lakefront park with skyline and water views
  • DuSable Black History Museum – Celebrating African American history and culture