New Eastside

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Planning a large group getaway to Chicago, but don’t want to get under each other’s toes? This trio of apartments in the same high-end serviced apartment complex should do the trick. In each home expect two boutique-style bedrooms and bathrooms, a made-for-action kitchen, and a private balcony to take in those sweeping vistas of West Loop. When it’s time to get together, the rooftop communal sky lounge and outdoor terraces, complete with fire pits, should do nicely. Location-wise, West Loop's local gems, including Little Italy and Union Park, are all within easy reach on foot, so having a car isn’t a dealbreaker here.

Windy City Wonder

Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions. Landmarks that whisper tales of architectural glory and river cruises that awaken the senses are but a stroll away. Amble over to Millennium Park or the Chicago Riverwalk, each reflecting city's charm in their unique ways. State Street is replete with gastronomic gems and shopping opportunities for those with an inclusive palette. Immerse in city's essence as you experience the wonders it has to offer.

Chicago Chill Pad

Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City. Experience traditional Chicago history infused with Italian villa architecture and other internationally inspired design details. From the moment you step through the door of this cultural haven, you'll be swept away by its enchanting atmosphere. Immerse yourself in the warmth and elegance of the Villa Vista, a tranquil urban oasis where timeless charm blends seamlessly with contemporary comfort. Indulge your senses as you admire the breathtaking cityscape views from the rooftop terrace or unwind in the peaceful courtyard. Whether you're here for a weekend getaway or an extended stay, you'll find everything you need for a truly memorable experience at this charming Streeterville retreat.

Culture Haven

Welcome to our charming haven, nestled in the vibrant neighborhood of River West, Chicago. This urban oasis offers a serene escape from the bustling city, allowing you to experience the best of both worlds. Immerse yourself in the tranquil ambiance of this rustic chic retreat and be captivated by its unique features. The lush, secret garden hideout is perfect for unwinding, while the picturesque river views will soothe your senses. Step inside to discover a stylishly decorated space, blending modern loft living with vintage charm. Each room is designed with comfort and relaxation in mind, offering a cozy and intimate atmosphere. Indulge in culinary delights at nearby trendy restaurants or explore the eclectic mix of shops and bars that make this neighborhood so exceptional. Experience Chicago like never before at this whimsical riverside retreat.

Westside Retreat

Step into 'The Chevelle', your unexpected sanctuary nestled amidst Chicago's lively West Loop. Previously a symbol of industrial prowess, this neighborhood is now an epicenter of world-class dining and simmering nightlife. The environs beckon with an alluring mix of upscale boutiques and a vintage market, summoning both the modern hipster and the discerning antique enthusiast. Echoes of blaring horns from steam engines are replaced by laughter, chatter, music - sounds infusing the air with life and a love for city living. As you breach the threshold of 'The Chevelle', you are greeted with safety measures designed to create a secure, comfortable environment. While security is emphasized it never overshadow the feeling of being home away from home. A little bit nostalgic, majorly comfortable, the holiday home in West Loop embraces its past even as it looks towards the future, much like Chicago itself.

The Windy City Retreat

Immerse yourself in the experience that is The Zeus, centrally positioned in the exciting Streeterville neighborhood. Here, a unique blend of classic allure fuses with an internationally inspired design that echoes Italian villa architecture. The traditional history of Chicago entwines brilliantly with high-end modern lifestyle preferences to create a one-of-a-kind atmosphere, tucked away in the heart of The Windy City. Surrender to the pulsing rhythm of downtown city life Meshing effortlessly with extraordinary elegance and an indescribable sense of comfort sets this dwelling resolutely apart. Please note: guests must pass verification and provide valid ID.

Italian Villa Immersion

High above River West, this spectacular home with skyline views invites you to experience Chicago at its most inspiring. Floor-to-ceiling windows keep the city close at every moment, while the balcony gives you a private stage for sunrise coffees and evening cocktails under glittering lights. Spend your days exploring, whether it's the food halls of Fulton Market, art at the MCA, or strolls along the Riverwalk. Then come home to swim at sundown, gather with a glass, or simply let the skyline remind you why you came. Here, Chicago feels expansive, electric, and entirely yours.

Skyline Reverie

Welcome to The Jordan! Nestled in Chicago's iconic Chicago Loop, this urban oasis provides a tranquil retreat amidst the bustling cityscape. Immerse yourself in the architecturally rich Financial District, surrounded by historic landmarks and breathtaking skyscrapers. Indulge in an enchanting experience, gazing at the mesmerizing city lights from your private rooftop terrace. Accented with modern amenities, this Metropolitan Hideaway seamlessly combines style and comfort. Explore the vibrant neighborhood filled with renowned dining and shopping destinations, or simply unwind along the scenic Chicago Riverwalk. Whether you're seeking a relaxing escape or a hub for urban adventures, The Jordan offers cosmopolitan comfort in the heart of Chicago's downtown. 

Loop Haven

Welcome to a distinguished spot nestled in the vibrant pulse of the West Loop! All visitors are skillfully screened for safety and a damage hold is acquired prior to stay. Blissfully positioned steps away from ritzy dining and euphoric nightlife venues, this loft situates you right in the hub of excitement. An eclectic blend of high-end boutiques infuse an additional dash of flair to your visit. Indulge in the nostalgic echo of yesteryears through the vintage market close by.

Windy City Haven

Welcome to a dazzling retreat in the heart of West Loop. A vibrant ambience invites you to immerse yourself, enveloped by the rhythm of the city's live music and savory aromas from nearby culinary gems. Across its former industrial terrain are now an array of dining and nightlife attractions, fashion-forward boutiques and a vintage market - a palette of sensory delights at your fingertips. Comfort meets thrill in this urban oasis rich with character and eager to create memorable experiences. Please note that to ensure guest safety we have an inclusive screening process which includes ID verification.

The West Wind Charm

All resting eyes behold a unique sanctuary blending urban spirit with an enchanting skyline whisper. The escape, nestled in the heart of Chicago's cherished West Loop, extends far beyond the eye, unfolding boundless options for dining, shopping, and entertainment. As one engages with this gem place guests find themselves embraced by a blanket of luxury sensibility without bounds. The wonder is further heightened in the private balcony serenely gazing at the skyline views, washing away all traces of mundane daily hassles, all set to embark you on a journey to rejuvenation and pure relaxation.

Chicago's Gemstone

A striking interplay between tradition and trend elevates this property nestled within the vibrant Streeterville neighbourhood. Combining nostalgic tales of Chicago's history with an undercurrent of worldwide allure, it resonates an Italian villa's flair and far-reaching design sensibilities. Here, the city's ceaseless energy meets a haven of international vibes. As you step inside, the culture-imbued downtown lifestyle ebbs away to early European architecture, allowing you to luxuriate in your private sanctuary amid The Windy City's dynamic heart. Indulge in this cultural infusion where chic urban living and classic charm coexist, providing an unmatched tranquil experience for discerning guests. Your idyll awaits at the city centre where leisure and convenience come naturally.

The Urban Villa

United Kingdom luxury cottages

England luxury cottages

Wales luxury cottages

Scotland luxury cottages

Edinburgh airbnb alternatives

York airbnb alternatives

Cornwall luxury cottages

Cumbria luxury cottages

Devon luxury cottages

Dorset luxury cottages

Kent luxury cottages

Norfolk luxury cottages

Northumberland luxury cottages

Pembrokeshire luxury cottages

Somerset luxury cottages

Suffolk luxury cottages

The Cotswolds luxury cottages

Yorkshire cottages

United Kingdom

London airbnb alternatives

London luxury aparthotels

London luxury serviced apartments

London luxury short stay rentals

London luxury vacation rentals

London

Paris airbnb alternatives

Paris luxury aparthotels

Paris luxury short stay rentals

Paris luxury vacation rentals

Paris

Los Angeles airbnb alternatives

Los Angeles luxury vacation rentals

New York airbnb alternatives

New York luxury short stay rentals

New York luxury vacation rentals

Joshua Tree airbnb alternatives

Palm Springs airbnb alternatives

Palm Springs luxury vacation rentals

San Diego airbnb alternatives

United States

Italy luxury villas

Rome airbnb alternatives

Rome luxury vacation rentals

Milan airbnb alternatives

Florence airbnb alternatives

Venice airbnb alternatives

Apulia Luxury Villas

Sicily luxury villas

Tuscany luxury villas

Lake Como

Sorrento airbnb alternatives

Amalfi Coast airbnb alternatives

Italy

Spain luxury villas

Barcelona airbnb alternatives

Barcelona luxury aparthotels

Barcelona luxury vacation rentals

Madrid airbnb alternatives

San Sebastian airbnb alternatives

Canary Islands luxury villas

Costa del Sol luxury villas

Ibiza luxury villas

Malaga airbnb alternatives

Mallorca luxury villas

Marbella luxury villas

Spain

Portugal luxury villas

Lisbon airbnb alternatives

Porto airbnb alternatives

Algarve luxury villas

Madeira luxury villas

Portugal

Greece luxury villas

Athens airbnb alternatives

Crete luxury villas

Corfu airbnb alternatives

Mikonos airbnb alternatives

Rhodes luxury villas

Santorini airbnb alternatives

Greece

Berlin airbnb alternatives

Cape Town

Copenhagen airbnb alternatives

Dubai airbnb alternatives

Tel Aviv airbnb alternatives

Barbados luxury villas

Cyprus luxury villas

French Riviera luxury villas

Other

Top Destinations

Destinations

New Eastside Accommodation

New Eastside Accommodation for Groups

New Eastside Airbnb Alternatives

New Eastside Boutique Hotel Alternatives

New Eastside Holiday Rentals

New Eastside Hotel Alternatives

New Eastside Long Stay Rentals

New Eastside Monthly Rentals

New Eastside Self-Catering Apartments

New Eastside Short Stay Rentals

New Eastside Vacation Rentals

Types

Book a stay in one of the best homes in New Eastside

We selected the 72 homes worth renting in this location

Who's coming along?

Home spotlights in New Eastside

We selected the top 3% holiday homes in New Eastside

Most popular homes in New Eastside

Check upcoming rates & availability for New Eastside

Frequently asked questions