Townhome vacation rentals in North Side

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Top-rated townhouse rentals in North Side

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Guest favorite

Townhouse in Chicago

4.98 out of 5 average rating, 229 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

The newly renovated spacious apartment is furnished with brand new modern king bed in the bedroom to ensure restful nights. In large living room, beautiful cherry dining table to enjoy morning coffee and comfortable L-shape leather sofa for watching your favorite movies from Netflix on 43" flat screen TV. The brand new fully equipped kitchen has a granite countertops, stainless steel appliances. The modern marble bathroom has a huge mirror over the sink, glass sliding shower doors, a full size bath tub and a hair dryer. Spacious 3 room apartment with all the amenities specified above is for guests use only and free residential parking permits provided upon request. I'm always available. I live on the 2nd floor of the townhouse with my husband and work at a bridal boutique which I own on west Armitage Ave. The apartment is super conveniently located in the Armitage/Sheffield. It's 2 1/2 blocks or 5 minutes walk to both Brown and Red line stations which make getting around Chicago fast and easy. Visiting lake front Millennium Park takes less than 20 minutes from the apartment. My neighborhood is surrounded by Old Town, full of local shops and restaurants, Wrigley Field, eclectic Bucktown shops, and the Lincoln Park Zoo. The 3 Michelin-starred restaurant, Alinea is 2-minute walk from the door. Take either Red ( North/Clybourn ) or Brown (Armitage/Sheffield ) line for exploring Rush st( 1 stop) Water Tower, Michigan Ave, Mag miles, Gold Coast( 2 stops ) The Navy Pier( 3 stops) Millennium Park, Cloud Gate/ The Bean, Buckingham Fountain, Art Institute of Chicago,( 4stops). Both stations are within 5 min walking distance from the apartment. It's also a short cab or Uber ride to Michigan Ave. Gold Coast. No smoking, no street shoes, no parties allowed. The nightly rates are for 2 guests only and $25 guest fee applys for 3rd guest. There is a $500.00 penalty for breaking the each rule.

Oct 2 – 9

G$43,510 GYD per night

Superhost

Townhouse in West Town

4.87 out of 5 average rating, 141 reviews

⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️

Cozy, comfy garden apartment that sleeps up to 4 people with access to the patio w/ fire pit and rooftop deck. Located right next to the underground train stop. A quick trip to Downtown & hip Wicker Park/Logan dining, shopping & nightlife. A straight shot from ORD on the Blue line Normal check-in is 4 pm. Bag drops possible as early as noon. I will notify you if an early check-in is possible on the day of arrival. Please be flexible with check-in times if booking with less than 24 hours’ notice

Aug 6 – 13

G$32,268 GYD per night

Guest favorite

Townhouse in Chicago

4.93 out of 5 average rating, 187 reviews

A Cozy Oasis - Guest Favorite Logan Square Chicago

On a quiet cul-de-sac in Logan Square, this home is a serene oasis. Steps away from Milwaukee Ave's renowned restaurants, bars, Revolution Brewery, Stan Mansion, and The Whale, 606 trail, Blue Line to airports and downtown, as well as Bucktown and Wicker Park. Logan Square Public Library is a block away. Enjoy a self-check-in process, free street parking, fully equipped kitchen, 3 BR, 1 bath, and amenities like a washer, dryer, and yard. Please note, Per Chicago regulations, no parties allowed.

Jan 21 – 28

G$39,597 GYD per night

Superhost

Townhouse in Chicago

4.8 out of 5 average rating, 156 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

Jan 16 – 23

G$63,784 GYD per night

Guest favorite

Townhouse in Chicago

5.0 out of 5 average rating, 19 reviews

𓃥Wicker Cozy Corner

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking and EV charging. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.

Oct 4 – 11

G$69,938 GYD per night

Guest favorite

Townhouse in Chicago

5.0 out of 5 average rating, 210 reviews

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Feb 16 – 23

G$172,178 GYD per night

Guest favorite

Townhouse in Chicago

5.0 out of 5 average rating, 26 reviews

Modern Townhome With King Suite & Private Patio

Welcome to Bucktown! This property lives like a single family home and consists of a private patio, 2 spacious living rooms, 5 beds, and 3 bathrooms. This bright and colorful modern townhome is perfect for families, professionals, and groups! Our townhome is also pet-friendly ($175 per pet for the stay). Our home sits on the corner of a very quiet and safe block surrounded by amazing neighbors! Their comfort and trust is important to us! Please respect our homes quiet hours from 9PM- 8AM.

Sep 4 – 11

G$132,181 GYD per night

Guest favorite

Townhouse in Chicago

4.9 out of 5 average rating, 73 reviews

Enjoy Chicago/suburbs 2BR townhouse fully equipped

Imagine yourself in the heart of Chicago, just minutes away from the charming suburbs. Picture strolling through Oak Park, the hometown of Hemingway, with its vibrant downtown, tempting eateries in Elmwood Park, Forest Park's allure, and the hidden gems of River Grove. Feel the excitement as you walk to the Metra station, your gateway to downtown Chicago. Don't miss out on this captivating experience—book your stay now and immerse yourself in the vibrant tapestry of the Windy City.

Jan 3 – 10

G$33,484 GYD per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Feb 19 – 26

G$20,296 GYD per night

Guest favorite

Townhouse in Chicago

4.97 out of 5 average rating, 122 reviews

*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*

• 4 bedrooms (3 queens, 3 twins, and 2 futons) • free private dedicated outdoor parking space • close to popular neighborhoods such as Wrigleyville (6 min drive), Andersonville, and Uptown • easy access to public trains (Metra, Red line Wilson and Brown line Montrose stops) and buses • 20 min to downtown Chicago by car • Easy access to Evanston by Metra (Ravenswood train stop) - 4 stops • Close to Montrose Beach • 94/100 walking score

Sep 25 – Oct 2

G$130,850 GYD per night

Guest favorite

Townhouse in Chicago

4.85 out of 5 average rating, 276 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Nov 3 – 10

G$20,805 GYD per night

Guest favorite

Townhouse in Chicago

4.89 out of 5 average rating, 70 reviews

Insta-worthy Townhome w/ King Suite &Rooftop Oasis

2024 BOOKING SPECIAL! No cleaning fee $0. GUEST PARKING PASSES PROVIDED. Enjoy a stylish experience at this centrally-located home in desirable Lincoln Park. Family friendly! This location is hard to beat! Once booked I will send you my guidebook full of some of the best restaurants, bars, local highlights as well as some tips and tricks so you can start planning and make the most out of your visit to Chicago!

Dec 3 – 10

G$112,233 GYD per night