Holiday rentals with a fireplace in Old Town

4.94 out of 5 average rating, 241 reviews

The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.

Apartment in Old Town

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

4.88 out of 5 average rating, 156 reviews

Home in Old Town

Huge Downtown Gem *Yard *Parking *Fireplace

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques; Lincoln Park and North ave beach from this three-level house. 5 bedrooms, 3.5 baths, 2 fully stocked kitchens, 2 car garage, back yard, laundry, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22. Message me if you have any questions!

4.76 out of 5 average rating, 229 reviews

Townhouse in Old Town

Heart of the City Group Hub • Patio • Fireplace

Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, Lincoln park zoo, restaurants, bars, boutiques. Bring family or friends to this Haute Couture Designer themed townhouse spanning over two levels on a quiet neighborhood street in historic Old Town. 4 bedrooms, 2.5 baths, patio, parking for 1 car, laundry, fully stocked kitchen with stainless steel appliances & granite countertops. Pets welcome! What else can you possibly need? Message me if you have questions!

4.89 out of 5 average rating, 135 reviews

The master bedroom features a spacious king-size bed dressed in soft linens, complemented by a flat-screen television mounted on the wall. Natural light filters in through the door leading to the en-suite bathroom, while neutral tones create a calming environment.

Apartment in Old Town

Family-Friendly 2BD/2BA Prime Location (+parking)

Getaway to this authentic Old Town apartment! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Luxurious interior design - Master en-suite w/ all the bells/whistles! - Extremely Fast WiFi - Pillow-top Bamboo mattresses - Charming neighborhood - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

4.96 out of 5 average rating, 117 reviews

A sunlit patio area features a wooden table surrounded by four chairs on a patterned blue rug. The scene overlooks a grassy field with people playing in the distance, framed by a decorative black fence under a clear blue sky.

Townhouse in North Side

Hidden Gem - 3 Story House & Pet Friendly!

Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

4.88 out of 5 average rating, 112 reviews

A modern living space features light hardwood flooring and gray walls. Artwork depicting Chicago is displayed on the wall. A glass coffee table rests on a patterned rug, surrounded by a gray sofa and a chic armchair. An elegant dining area accommodates six guests.

Home in Ranch Triangle

Sophisticated Twnhm in Prestigious Lincoln Park

Welcome to our awesome townhome, nestled in a peaceful residential neighborhood, offering both convenience and serenity. Located with easy access to public transportation, you can explore all that Chicago has to offer. There are multiple levels to this townhome with stairs. A bedroom and bathroom on the ground floor, kitchen and living/dinning room on the middle floor, and the master bedroom with master bathroom on the top floor. A mini roof top to enjoy Chicago nights as well.

Holiday home in Lincoln Park

An inviting living room features a spacious grey sectional sofa and two orange accent chairs, arranged around a glass coffee table. A decorative area rug covers the hardwood floor, while built-in shelves display books and a television is set into the corner near a fireplace.

4.97 out of 5 average rating, 114 reviews

The Belden Belle: The Luxurious Chicago Townhouse

Welcome to our home! This centrally located neighborhood escape puts you right in the center of everything. You will be just minutes from major city landmarks like the Lincoln Park Zoo, the History Museum, beautiful Fullerton Beach, and some of the best dining and entertainment spots in all of Chicago. Suitable for couples, single traveling adventurer, business traveller, families (with children) and big groups. Free WiFi available. Surrounded by everything Chicago has to offer!

Townhouse in Near North Side

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

4.91 out of 5 average rating, 167 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Condo in Old Town Triangle

A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.

4.87 out of 5 average rating, 188 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Apartment in Magnificent Mile

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

4.99 out of 5 average rating, 138 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

Apartment in Near North Side

A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.

4.92 out of 5 average rating, 174 reviews

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Townhouse in Lincoln Park

A spacious living room features a comfortable white sectional couch positioned on a light area rug. A sleek glass coffee table is centered in front of the couch. A modern media console with wall-mounted shelves displays decorative items, while natural light streams through a large window with sheer coverings.

4.86 out of 5 average rating, 230 reviews

Cheerful 3 story townhouse Old Town/LP

Discover a luxurious three-story townhouse, ideally located for exploring Chicago's Lincoln Park Zoo, Lake Michigan, Magnificent Mile, Old Town, and Lincoln Park's vibrant dining and shopping. Enjoy a complimentary designated parking spot. Please note: due to a host's medical condition, we cannot accommodate service animals that are cats or dogs. A fee applies for more than two guests.

Popular amenities for Old Town Accommodation with Fireplace

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

4.97 out of 5 average rating, 108 reviews

A spacious kitchen area is shown with modern stainless steel appliances and ample cabinet storage. A large wooden dining table is centered, set with decorative placemats. Soft light illuminates the room, complementing the neutral color scheme of the walls and cabinetry.

Home in Des Plaines

Newly remodeled O’hare oasis

4.94 out of 5 average rating, 101 reviews

A modern kitchen featuring stainless steel appliances, including a refrigerator and gas range. A spacious island with white marble countertop is surrounded by light-colored chairs. Above, stylish pendant lights provide ample illumination, while the open layout invites natural light from adjacent glass doors.

Home in West Town

NEW! 3BR/2.5B Duplex in Noble Sq

4.85 out of 5 average rating, 333 reviews

A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.

Home in River West

Lux Urban 3BR/3BA Duplex + Parking!

4.89 out of 5 average rating, 206 reviews

A spacious living room features a large navy sofa adjacent to a modern coffee table on a textured rug. Colorful artwork adorns the walls, and a flat-screen TV is mounted for entertainment. Light streams through windows, enhancing the open, airy atmosphere.

Home in Lake View

Lake View | Wrigley Designer House w/Patio

4.96 out of 5 average rating, 120 reviews

A modern kitchen and dining area features sleek cabinetry and a large window allowing natural light. A glass dining table with blue chairs is positioned centrally, adjacent to stainless steel appliances and counter space. Light hardwood flooring enhances the spacious look of the room.

Home in Mayfair

Northside Chicago Getaway

4.95 out of 5 average rating, 111 reviews

A bright living area showcases a cozy seating arrangement with a light blue and white sofa set. A modern fireplace is centered beneath a wall-mounted TV. Decorative shelves feature various items. Natural light filters in through the windows, enhancing the spacious feel.

Home in Lake View

Entire house w/ free parking, close to Wrigley!

4.88 out of 5 average rating, 145 reviews

A modern living room features a large, curved green sectional sofa and a blue accent chair. A round, light-colored coffee table sits at the center, complemented by decorative items. Large windows provide natural light, while an artistic light fixture enhances the space.

Home in Lake View

Soak Up Mid-Century Style in Wrigleyville and Boystown

4.96 out of 5 average rating, 91 reviews

A charming Victorian home is framed by lush greenery and vibrant trees. The front entrance features a set of steps leading to a stylish door, complemented by a small outdoor seating area visible to one side.

Home in North Side

Beautiful Lincoln Park House

Apartment rentals with a fireplace

4.96 out of 5 average rating, 186 reviews

A three-story brick building is presented, featuring large windows and accent balconies adorned with plants. A stone pathway leads to the main entrance, while a small garden area is visible at the base, surrounded by a decorative black fence.

Apartment in Wicker Park

Hip Chicago Condo in fun shopping and dining area

4.96 out of 5 average rating, 296 reviews

The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.

Apartment in Evanston

Stylish & Comfy Gem near Downtown~Balcony~Parking

4.97 out of 5 average rating, 172 reviews

A vibrant living area features two orange armchairs positioned around a decorative wooden table. A floral wallpaper adorns the wall behind a wall-mounted television, while a rich area rug anchors the space. Natural light filters through sheer curtains, highlighting the room's colors.

Apartment in Chicago

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

5 out of 5 average rating, 118 reviews

A spacious living room is highlighted by a large sectional sofa adorned with colorful cushions. A flat-screen television sits opposite a cozy fireplace, framed by light-colored bricks. Two windows allow natural light to fill the room, enhancing the relaxed ambiance.

Apartment in Lake View

Steps away from Wrigley Field!!

4.99 out of 5 average rating, 148 reviews

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

Spacious 2 Bedroom in the heart of Lakeview!

4.97 out of 5 average rating, 144 reviews

A modern living room features a large white leather sectional sofa positioned near a wall-mounted television. A sleek electric fireplace is located beneath the TV. Bright overhead lights illuminate the space, while potted plants and windows add natural accents.

Apartment in Chicago

Quiet city getaway by beach in fun neighborhood

4.99 out of 5 average rating, 143 reviews

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

CASA NEWPORT

4.97 out of 5 average rating, 444 reviews

The kitchen area features a modern design with wooden cabinetry and a sleek countertop. Four black bar stools are positioned at a counter, which faces an abundance of natural light from a window. The kitchen is equipped with new appliances and organized shelves for easy access.

Apartment in Chicago

Peaceful River West, free parking

Villas with a fireplace

4.82 out of 5 average rating, 17 reviews

The rooftop deck features a spacious seating area adorned with colorful cushions and throws, inviting relaxation. A table is set for outdoor dining, with a scenic backdrop of the Chicago skyline, including the Willis Tower. Bright blue skies add to the vibrant atmosphere.

Villa in West Town

HUGE!3BRPrivateHome+Garage+360°Roof+HotTub+EV+12pp

4.66 out of 5 average rating, 56 reviews

A grand piano occupies the foreground, showcasing a polished surface that reflects light. Behind it, a spacious area is visible with a row of blue chairs and a ceiling adorned with modern chandeliers, highlighting the open and elegant design of the indoor space.

Villa in South Shore

Rooftop | Villa | Events