Holiday houses in Ravenswood

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Quick stats about holiday rentals in Ravenswood

  • Total holiday rentals

    Explore 100 holiday rentals in Ravenswood

  • Nightly prices starting at

    Ravenswood holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 11,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Ravenswood holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ravenswood rentals

  • 4.9 Average rating

    Ravenswood stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Ravenswood

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

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Top Guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park
4.99 out of 5 average rating, 108 reviews

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.

ValueLocationSolo travel

Top Guest favourite
An airy studio bedroom features a spacious bed with white linens and decorative pillows. Large windows allow natural light to fill the room, showcasing a cozy sitting area with a small table and chair. Framed botanical artwork adorns the walls, contributing to a calming ambiance.
Guest suite in Ravenswood
4.99 out of 5 average rating, 435 reviews

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

LocationValueBathroom

Top Guest favourite
A comfortable living area is featured, showcasing a full size futon and two teal armchairs arranged around a wooden coffee table. A television sits on a rustic console, and natural light filters through glass block windows.
Guest suite in Lincoln Square
4.96 out of 5 average rating, 352 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Level 2 EV charger available.

LocationValueDecor

Top Guest favourite
A bright bedroom features a spacious bed with white linens. A piece of abstract art adorns the wall above a desk with a wooden chair. A doorway leads to a cozy sitting area with a blue couch and a yellow accent chair, illuminated by natural light.
Apartment in Lake View
4.99 out of 5 average rating, 359 reviews

A Stylish, sundrenched Chicago Ravenswood Flat

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

LocationValueBreakfast

Top Guest favourite
A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.
Home in Ravenswood
4.99 out of 5 average rating, 148 reviews

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!

LocationFamilyAccess

Top Guest favourite
A spacious living area features a fireplace with a decorative mantle and a large television. Two bright red armchairs are positioned across from a modern coffee table. Light streams in through windows, illuminating the hardwood flooring and surrounding decor.
Apartment in Ravenswood
4.92 out of 5 average rating, 252 reviews

Comfortable Vintage North Side Retreat for 8

If you love Mid-Century Modern decor you will love this apartment. The light-filled main family room and sun porch is the perfect place to recharge after a long day of sightseeing. There are 3 bedrooms and a sofa that pulls out into a queen bed to comfortably accommodate 8 guests. A large dining table and functional kitchen means you have the option to cook in or dine out while exploring the city. I provide all the essentials to make your stay easy and comfortable.

ValueFamilySleep quality

Top Guest favourite
A charming front porch features a small round table surrounded by two wrought iron chairs. A cozy seating area is adorned with a vibrant red blanket. Flower planters filled with lush greenery and colorful blooms enhance the inviting ambiance, with sunlight filtering through the trees.
Condo in Ravenswood
4.96 out of 5 average rating, 149 reviews

Best Lincoln Square location. Spacious 2 bedroom

Charming home in an updated 1800's beautiful brick building. High ceilings, spacious, loads of windows and antique furnishings. Located in the heart of Chicago's Lincoln Square. 2 blocks to the El train. Walk to movies, restaurants, bars, parks. Lovely quiet & upscale neighborhood. Bike to the beach & downtown. 2 blocks from Old Town School of Folk Music. Inquire about our Cubs Season Tickets! Space is ideal for adults and families with children over 10 yrs.

LocationValueQuiet

Guest favourite
The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.
Guesthouse in Chicago
4.88 out of 5 average rating, 389 reviews

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!

FamilyLocationIndoor spaces

Top Guest favourite
A cozy living room features a light-colored sofa adorned with two decorative pillows. A coffee table is centered on a patterned rug, showcasing a floral centerpiece. A comfortable chair is positioned beside a window, with a lamp providing soft illumination. Natural light enhances the space.
Apartment in Lincoln Square
4.99 out of 5 average rating, 116 reviews

Cozy & Quiet Hideaway in Lincoln Square

This charming apartment is located on the 3rd floor of our home nestled in a lovely residential street steps from the heart of Lincoln Square. With it's huge kitchen and workspace, comfy living room and cozy bedroom with a queen-sized bed, this is perfect for a couple visiting friends or family in the area or a single person here for work. With it's vibrant, family-oriented scene and many unique shops and restaurants, you'll definitely enjoy your stay!

ValueFamilyGetting around

Top Guest favourite
A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.
Apartment in Ravenswood
4.95 out of 5 average rating, 437 reviews

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.

FamilyValuePets

Guest favourite
A charming multi-story home is presented, featuring a covered porch with steps leading to the entrance. Flower baskets are hung from the railing, surrounded by lush greenery and well-maintained shrubs. Bright sunlight illuminates the exterior, highlighting the texture of the siding.
Guest suite in Ravenswood
4.86 out of 5 average rating, 212 reviews

Cozy space in Lincoln Square

A nice quaint suite located on a quiet street in the heart of Lincoln Square/Ravenswood area. Two blocks from the Rockwell Brown line 'L' stop and just steps from CTA bus stops. We are a few blocks northwest of the main square that has lots of shopping and restaurants. Great festivals and parks for summer fun. Close to bike trails along the Chicago river and Lake Michigan. (PLEASE NO ANIMALS)

ValueFamilySleep quality

Top Guest favourite
A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.
Condo in Ravenswood
4.97 out of 5 average rating, 498 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. We live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

ValueFamilyParks

Popular amenities for Ravenswood holiday rentals