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Holiday houses in Boystown

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Top-rated holiday rentals in Boystown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A spacious living area features an exposed brick wall complemented by large windows allowing natural light in. A sectional sofa is arranged around a round coffee table atop a patterned rug, and a modern light fixture hangs from the ceiling. A television is positioned on a clean-lined media console.
Condo in Lake View
4.87 out of 5 average rating, 142 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Top Guest favourite
A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.
Apartment in Lake View
4.95 out of 5 average rating, 258 reviews

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

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Top Guest favourite
Condo in Lake View
4.98 out of 5 average rating, 251 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Guest favourite
Apartment in Wrigleyville
4.77 out of 5 average rating, 257 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

You can’t beat this location! Right in the middle of Boystown and steps from Wrigley Field, you’ll be surrounded by some of the city’s best bars, restaurants, and nightlife. Cubs Stadium is just one block away, and the Addison Red Line station is a quick 5-minute walk, making it easy to explore all of Chicago. No shared space: Due to updated COVID-19 policies, this unit is now 100% private. Once you book, the entire place is yours and the additional listing will be blocked immediately.

Guest favourite
A modern dining area features a wooden table surrounded by six chairs. Natural light enters through large windows, highlighting the grey walls and stylish cabinetry. A chandelier hangs above the table, while a wall-mounted art piece adds a decorative touch to the space.
Condo in Wrigleyville
4.9 out of 5 average rating, 166 reviews

Foosball, Steps from Wrigley, Private Parking

Our apartment is ideally located near Wrigley Field and just steps from the Red Line, making it extremely convenient for exploring Chicago. Because of this prime location, occasional train and street noise can be heard. To help you sleep comfortably, we provide ear plugs. Many of our guests still enjoy the vibrant city atmosphere while finding the apartment cozy and restful. Perfect For: Guests who love being in the heart of Chicago and don’t mind a bit of city life sounds.

Top Guest favourite
An elegant stone entrance is framed by lush green ivy, leading to a wooden door beneath a decorative awning. A charming fountain, featuring three tiers, adds a serene element to the outdoor area, surrounded by abundant foliage and creating a peaceful environment.
Apartment in Lake View
4.99 out of 5 average rating, 152 reviews

CASA NEWPORT

Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have air conditioning. It does have a window unit in the bedroom from May to September.

Top Guest favourite
A spacious living area is furnished with two leather sofas, a coffee table, and a decorative rug. A television is mounted above a tiled fireplace, and large windows allow natural light to fill the room. A comfortable armchair is positioned near the window.
Apartment in Lake View
4.99 out of 5 average rating, 152 reviews

Spacious 2 Bedroom in the heart of Lakeview!

Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

Guest favourite
The contemporary kitchen features sleek stainless steel appliances and quartz countertops. A stylish overhead light fixture illuminates the space. A cozy dining area is positioned nearby with high-backed stools contrasting against the light cabinetry and textured wall.
Apartment in Lake View
4.85 out of 5 average rating, 525 reviews

Sleek and cool garden loft in East Lakeview

Cool loft 1 bedroom, queen bed in bedroom, 2nd queen bed in living area. Contemporary custom kitchen with quartz counters and stainless appliances. In unit laundry with central heat and air. Within walking distance to Lake Michigan, Belmont Station, Wrigley Field, Briar Street Theater, The Vic, Belmont Theater District, too many restaurants to mention and lots of retail shopping. 24 hour Starbucks nearby, Free Wifi and Netflix

Top Guest favourite
An open-concept living area is featured, showcasing a dark sofa complemented by light-colored pillows. A round coffee table sits on a patterned rug, and a dining area for four is visible nearby. Modern kitchen appliances are neatly arranged against the backdrop of sleek cabinetry, with natural light flowing through a large window.
Apartment in Wrigleyville
4.96 out of 5 average rating, 161 reviews

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Guest favourite
Apartment in Lake View
4.93 out of 5 average rating, 229 reviews

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.

Guest favourite
The exterior of a garden unit is visible, featuring a red door framed by large windows. A locking fence surrounds the entrance, with low shrubs and a small area of gravel alongside the pathway. The building's brick facade provides a classic urban feel.
Apartment in Wrigleyville
4.81 out of 5 average rating, 481 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.

Top Guest favourite
The facade of a historic greystone building is showcased, featuring intricate stonework and large windows. A wrought-iron fence adorned with vibrant pink flowers is visible in the foreground, adding a touch of natural beauty to the entrance.
Condo in Wrigleyville
4.99 out of 5 average rating, 113 reviews

Wrigleyville Inn. Historic Greystone, Free Parking

Have fun with the whole family at this stylish place. Completely rehabbed 3 bedroom 2 bathroom high end, 1st- floor condo in a historic greystone, 5-minutes walk to Wrigley Field. And only 2 minutes walk to Clark or Halsted Streets. New open back porch for your enjoyment. Parking included. Old Grey Lady being reborn. Total gut rehab of classic Chicago 3 flat located in Historic Newport Avenue District.

Popular amenities for Boystown holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Northalsted