Luxury  Stays. oPERATED mASTERFULLY


Award-winning, luxury short term rentals. Comprehensive property management

Hospitality In Our DNA. Management In Our Heart.
Hubbard is a Chicago-based real estate company offering two distinct, best-in-class services — premium short-term rentals wrapped in elevated urban experiences, and full-service NOI-optimizing property management for building owners.


We operate and manage a portfolio of thoughtfully designed short-term rentals across the country's most sought-after neighborhoods, combining travel comfort with professionally managed experiences. Additionally, Hubbard brings institutional discipline to operating multi-family buildings — from revenue optimization and leasing to maintenance to financial reporting.


With 25 years of real estate experience and leadership, we hold every aspect of our business to the highest standards — whether that's delivering five-star guest stays or ensuring building owners have full confidence in the performance of their assets.

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Featured Properties

stay Where You Can Be Together

Handpicked. Professionally designed. Perfectly located. Spacious & Luxurious. Browse our featured properties and book your stay.

where ownership meets opportunity



Most property managers maintain. We optimize. Whether you’re maximizing a short-term rental,

stabilizing a multi-family building, or maximizing property NOI — Hubbard is the partner for you.


From PHD-backed pricing intelligence and guest / tenant experience to institutional reporting and proactive asset

management, we bring the strategy, the systems, and expertise to maximize performance.

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Short-Term Rental Operations & Management

Top 1% of ADR-listings, occupancy, and guest ratings across every major platform.

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Long-Term Property Management
Comprehensive building management, operations, and reporting for multi-family assets.

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Integrated Short & Long-Term Management
A blended approach that combines short and long-term rental strategies to maximize unit occupancy, unlock enhanced revenue per square foot, and deliver superior NOI.

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Institutional Reporting
Monthly performance statements with the clarity and analytical intelligence your CPA and partners will appreciate.

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Flexible Deal Structures
Hubbard can master lease, manage or acquire your property. We build our strategy around your goals.

Building Performance You Can Write Home About

LET'S Discuss YOUR PROPERTY

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