
Places to stay near Winnemac Park
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Winnemac Park
Guests agree: these stays are highly rated for location, cleanliness and more.

Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

The Lincoln Square Hideaway
As you walk into your private 1st floor apartment from Western Ave, you’ll be greeted by a stunning wide-open great room. With 10+ foot ceilings, this previously commercial space provides ample enjoyment for the whole group. Add in the elegant boho design, and this Airbnb is one of a kind! Enjoy all of the amenities from home, a fully equipped kitchen, a large dining table, games (including Foosball), comfortable beds and seating, and more. All in the beautiful and walkable Lincoln Square!

Private Coach house near Lincoln Square!
Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

Andersonville Bicycle Studio
Enjoy a stylish experience at this centrally-located Andersonville studio. The Bicycle Studio leaves no detail untouched - modern amenities with the charm of exposed brick and timber beams. You are two blocks away from Chicago's popular Andersonville neighborhood - endless dining, shopping and entertainment. Quick access to public transportation and Chicago's lakefront. Quick Note: We are doing a home renovation July 1 - January 2027, so the air bnb will be unavailable during this time.

Bright Colorful Boho-Chic Studio in Lincoln Square
Kick back & relax in your home away from home in our modern & peaceful studio space with 15-foot ceilings in the heart of the Lincoln Square neighborhood. Featuring natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on the popular Foster Ave close to Winnemac Park, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Charming, Spacious 3BR Lakeview Apt Near Transit
This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Entire first floor in Lincoln Square!
First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Cozy and Private Andersonville Retro Studio
In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

Beautiful, sunny 2nd floor 3BR/1BA w free parking
Sunny second floor 3Br/1Ba apartment in the tree-lined, walkable neighborhood of Lincoln Square. Updated apartment with original woodwork offers easy access to Wrigley Field (7 el stops), Lake Michigan beaches, and downtown Chicago. Free parking space included, close to Western brown line el station and Lincoln Square's many restaurants and shops. Old Town School of Folk Music is a 5-minute walk. 2 miles to beaches.

Bright family-friendly Lincoln Square 2-bed 1-bath
Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Stylish & Modern 2 Bedroom Lincoln Square Condo
Unwind in our apartment with an open-plan design and refined feel. The cozy, contemporary boutique space features elegant furnishings and decor, as well as rustic touches throughout. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! General Policies: Guest Age Policy – Guests aged 18-24 may book on an exception basis.
Popular amenities for holiday rentals near Winnemac Park
Apartment rentals with wifi

Cozy Apartment with Free On-Site Parking

Lovely top floor 2BR/2BA, steps from everything!

The Bright Retreat in Andersonville

Best Lincoln Square location. Spacious 2 bedroom

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Newly updated 1BD/1B in Old Irving Chicago!

Cozy 3BR on Chicago's North Side & Free Parking

Near Lake Michigan & Wrigley Field
Family-friendly house rentals

Spacious Two Story Luxurious Home w/Outdoor Deck!

Division St Designer Home In Heart of Wicker Park

Private 3rd Floor Apartment

The Chicago River House – GIANT wall projector!

Victorian House in Heart of Rogers Park

Wrigleyville Southport Studio

Garden Unit in Malt Row

Cozy Bungalow Steps to Wrigley - Parking Included!
Apartment rentals with air conditioning

Andersonville Cozy 1 bedroom basement suite

Penthouse Near Wrigley Field

Stylish 2BR Andersonville — Walk to Lake & Cafés

Spacious 4 BR northside retreat sleeps 12/ Parking

Spacious, light-drenched studio-private entrance!

Cozy & Quiet Hideaway in Lincoln Square

Andersonville 2 bed with modern kitchen + bath

Modern Uptown Apartment - Clean & Close to Train!
Other great holiday rentals near Winnemac Park

Private, Charming, Coach House Loft in Andersonville

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Private suite in Lincoln Square

Cozy, Quiet, Garden Getaway!

Luxury Chicago Apartment

Cozy Andersonville Cabin

Great location, private entry and patio!

A+Chicago Roscoe Village Entire Home Wrigley+ More
Destinations to explore
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Brookfield Zoo
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- University of Chicago
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




