
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.

Whole Flat in Private Club. Walk to L, Dining & Shows
Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; 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

Stylish & Modern 2 Bed Lincoln Square Garden Condo
Unwind in our stylish garden 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. You're within walking distance of the heart of Lincoln Square, with local eateries and boutiques. Essentials are provided to make your stay easy and comfortable. Toilet paper, soaps, shampoo, towels, linens, laundry soap and even coffee! Book today and start planning your next Windy City Adventure!

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!

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.

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!

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 are Allowed!

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.

Two Bedroom Chicago Unit
Welcome to this spacious and stylish apartment just steps away from Clark Street, where you’ll find some of Chicago’s best restaurants, bars, and local charm. With downtown Chicago only a 20-minute drive or an easy train ride away, you’re perfectly located to explore the city. The space features modern furnishings, high ceilings, and plenty of natural light—offering a clean, comfortable vibe that’s perfect for relaxing after a day out.

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.
Popular amenities for holiday rentals near Winnemac Park
Apartment rentals with wifi

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

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Best Lincoln Square location. Spacious 2 bedroom

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

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

Spacious & Modern Family Friendly North Center Apt

Cozy and clean apartment in North Center

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
Family-friendly house rentals

Beautiful 4 BR Family Home near Wrigley

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

Chicago getaway for two!

Northside Chicago Getaway
Apartment rentals with air conditioning

Andersonville Cozy 1 bedroom basement suite

Stylish 2BR Andersonville — Walk to Lake & Cafés

Patio- 4 BR northside retreat sleeps 12/ Parking

Cozy apartment in Lake View

Cozy Nest in Chicago's Vibrant Lincoln Square

Cozy & Spacious Sunny 2 bedroom apartment.

3br W/ Elevator, Patio & Laundry Near the Red Line

Newly Renovated, Spacious 2BR in Andersonville
Other great holiday rentals near Winnemac Park

13 mins DT | 4 mins Lake | Artistic Loft Rooftop

Summer Break Incoming! Live Like an A-ville Local!

Private, Charming, Coach House Loft in Andersonville

Guest Favorite Newly Renovated 1BR Near Lakeview

Spacious Ravenswood Apartment

Gorgeous, cozy 1-bedroom Suite in Andersonville

Modern Design 2 Bd Condo In Iconic Lincoln Square

Cozy Andersonville Cabin
Destinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort
- Beachwalk Vacation Rentals





