Apartment vacation rentals in Old Town

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Top-rated apartment rentals in Old Town

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Top guest favorite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park
5 out of 5 average rating, 302 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Top guest favorite
The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.
Apartment in Old Town
4.94 out of 5 average rating, 236 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

Top guest favorite
Apartment in Old Town Triangle
4.77 out of 5 average rating, 262 reviews

Rare 1BR Lincoln Park Apt, close to everything!

Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Top guest favorite
A living area features natural light from multiple windows, complemented by a ceiling fan. A comfortable sofa with textured throws faces a modern fireplace. Two brown armchairs are positioned nearby, and a decorative rug lies under a coffee table, which displays a potted plant and a magazine.
Apartment in Evanston
4.99 out of 5 average rating, 100 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Guest favorite
A spacious living area features a gray sofa adorned with yellow cushions, accompanied by two beige armchairs. An archway leads to a contemporary kitchen, while soft lighting and a neutral color palette create a calm atmosphere.
Apartment in Lincoln Park
4.84 out of 5 average rating, 336 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history to its modern comforts. Featuring warm timber floors that connect two cozy bedrooms with queen beds to a contemporary kitchen. Each room has a TV, and the kitchen is fully stocked for your convenience. With two full bathrooms and barrier-free one-floor access, this space combines old-world charm with modern living in the vibrant heart of Lincoln Park, close to the Lakefront.

Top guest favorite
A comfortable living area is presented, featuring a brown sofa, light teal chairs, and a white coffee table. Soft lighting is provided by two lamps on either side of a teal accent table. Natural light filters through the window shutters, enhancing the cozy ambiance.
Apartment in Lincoln Park
4.98 out of 5 average rating, 419 reviews

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

Top guest favorite
An open living area features a dark leather sofa and a small wooden table atop a vibrant area rug. Natural light floods through two tall windows, framed by wooden shutters. A decorative fireplace is situated to one side, adding to the room's charm.
Apartment in Old Town Triangle
4.93 out of 5 average rating, 522 reviews

Victorian Guest Suite in Old Town

This private guest suite is the restored 1st floor of my Victorian era single family home. The space has a private ground floor entrance with small patio, located in the “Old Town Historic District”. Decor is Mid Century Modern. Located 1 block north of Sedgwick train station, bus stop across the street, 5 minute walk to the lake, 1/2 hour lakeside walk to downtown. Great restaurants nearby. Only registered guests are allowed on the premises. Please see booking requirements in house rules

Top guest favorite
A cozy living room features a large gray couch and two mustard-colored chairs. A small coffee table sits on a patterned rug, complemented by the soft glow of two table lamps. Natural light streams through multiple windows adorned with blinds.
Apartment in Lincoln Park
4.98 out of 5 average rating, 287 reviews

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck

A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.

Guest favorite
The living area features a spacious sofa and a cozy lounger chair, arranged around a central coffee table. Natural light enters through multiple windows, highlighting the hardwood floors. A workspace with a desk and a mirror is positioned nearby, complemented by decorative plants.
Apartment in Old Town
4.89 out of 5 average rating, 153 reviews

OLD TOWN GARDEN GETAWAY

Take it easy at this unique and tranquil getaway! Guests love this space because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Extremely Fast WiFi - Pillow-top Bamboo mattress and SMART TV in each bedroom - Exceptional workspace - 5-10 minute (0.4 mile) walk from Clark/Division red line station (CTA L) We look forward to hosting you!

Guest favorite
A bright bedroom features a spacious bed with crisp white linens, complemented by an abstract wall art piece. A wooden nightstand with a lamp is positioned beside the bed. Large windows provide natural light, showcasing views of the city beyond.
Apartment in Downtown Chicago
4.82 out of 5 average rating, 273 reviews

Kasa | Explore the Neighborhood-Mag Mile | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favorite
A cozy studio space features a sofa with blue cushions, complemented by a light wooden table and colorful accent wall. Natural light filters through the window, casting soft illumination. A television is positioned on a ledge, with a decorative statue nearby.
Apartment in Lincoln Park
4.84 out of 5 average rating, 325 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Guest favorite
Apartment in Old Town Triangle
4.86 out of 5 average rating, 335 reviews

Historic Old Town Flat - Minutes from Downtown!

Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!

Popular amenities for Old Town apartment rentals

When is the best time to visit Old Town?

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Quick stats about apartment rentals in Old Town

  • Total vacation rentals

    Explore 30 vacation rentals in Old Town

  • Nightly prices starting at

    Old Town vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

  • Verified guest reviews

    Over 3,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Old Town vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Old Town rentals

  • 4.7 Average rating

    Old Town stays receive an average rating of 4.7 out of 5 from guests

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