Holiday houses in South Pole

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Top-rated holiday rentals in South Pole

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

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Guest favourite
Apartment in Chicago
4.91 out of 5 average rating, 264 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

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Superhost
Home in South Side
4.91 out of 5 average rating, 33 reviews

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

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Superhost
A cozy parlor is adorned with vintage wallpaper featuring intricate patterns. Two upholstered couches are complemented by a small side table and a patterned area rug. Soft lighting is provided by table lamps, creating a warm ambiance in the inviting space.
Home in Chicago
4.95 out of 5 average rating, 19 reviews

Nostalgic Victorian Pullman City Cottage-3 Bd/2 Ba

FULLY REHABBED/transformed into a cozy Victorian home in Chicago’s unique Pullman Village, 20 mins by car from downtown. House is an 1800's time capsule rowhouse & the only truly period Pullman Airbnb, reflecting the area's Historic Landmark status. Stay here for a truly immersive extension of a Pullman National Park visit or the area's walking tours. Ideal for train/history/architecture/Park buffs, or just a quiet, unique place to unplug & live like olden days. Nostalgic as a stay at Grandma's!

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Superhost
A row of charming brick homes showcases American flags and seasonal decorations. A group of visitors gathers on the sidewalk, engaged in a guided tour. Lush greenery and colorful flowers surround the entryways, enhancing the neighborhood's inviting atmosphere.
Townhouse in Chicago
4.85 out of 5 average rating, 94 reviews

Large Executive Row house in Historic Pullman

Charming well appointed home w/exquisite furnishings. Safe, family friendly neighborhood w/shopping nearby. Walking distance to train station. Private entrance w/large rooms & plenty of space to host larger groups. We have everything from soaps to seasonings. Top quality new beds mattresses & linens. Walk to Pullman National Monument with visitors center staffed by US Park Rangers that feature state of the art interactive exhibits that appeal to all ages. Guided walking tours available.

LocationFamilyParking

Superhost
Apartment in Chicago
4.67 out of 5 average rating, 3 reviews

Stylish Retreat 85” TV, Surround Sound, Games

Welcome to your private 2nd-floor entertainment-ready **2-bedroom unit Kick back in front of the **85-inch flat-screen TV** with **surround sound built into the walls Turn the fun up with an **air hockey table and dart board. - **Bedrooms:** - **Master bedroom:** **King bed** - **Second bedroom:Two queen beds The galley kitchen is fully set up for simple meals and longer stays. Bathroom Highlights soaker tub, and Alexa built into the bathroom for relaxing music while taking a bath

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Top Guest favourite
Home in Whiting
4.92 out of 5 average rating, 130 reviews

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

LocationFamilyCheck-in

Guest favourite
A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.
Home in Chicago
4.91 out of 5 average rating, 133 reviews

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

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Top Guest favourite
A spacious dining area features a large wooden table with comfortable upholstered chairs, accommodating multiple guests. An elegant light fixture hangs above, providing soft illumination. The room connects seamlessly to the living area and kitchen, enhancing the open-concept design.
Bungalow in Beverly
4.96 out of 5 average rating, 45 reviews

Beverly Hills of Chicago Luxury Guest Favorite

Escape to luxury in this beautifully designed 5 bedroom, 3.5-bath home in Chicago's prestigious Beverly Hills neighborhood. Spacious living and high-end finishes, full finished basement have fun with air hockey, pool table, and video gaming, this entertainment space is for guests of all ages. Unwind on the private deck or enclosed front porch. explore retail shops and upscale dining. Metra train station provides a quick 15 minute downtown Chicago area. Close to downtown Chicago!

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Guest favourite
A spacious kitchen area is highlighted by a large table with wooden chairs, set against a neutral wall. Natural light filters through the window adorned with wooden blinds. A coffee maker and water bottles are seen on the countertop, with an appliance array visible in the background.
Apartment in Chicago
4.87 out of 5 average rating, 116 reviews

Lovely 1-BR Apt with full kitchen & living room

Kick back and relax in this calm, stylish space. We’re super excited to have you as our guest. This apartment is located on the 2nd floor (entrance from outside stairs). We are 30 minutes away from Downtown (no traffic), 4 minutes from Chicago Skyway and 11 minutes from Interstate 94. Enter your space through your own private entrance and make yourself at home. Your unit includes a private 1 Bedroom, 1 Bathroom, a Kitchen, Living Area with a sleeper sofa and desk.

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Top Guest favourite
A kitchen area features exposed brick walls, colorful accent walls, and wooden flooring. An island with a sun motif sits at the center, surrounded by three metal stools. A vase of flowers adds a touch of color, while a refrigerator stands against the adjacent wall.
Home in Chicago
4.95 out of 5 average rating, 119 reviews

Cozy, Artsy Gem in Historic Pullman

A getaway from the hustle and bustle of downtown; accessible to major highways. The rehabbed interior showcases art from local artists. The neighborhood was built in the late 1800s and is within walking distance of the Visitor Center, Exhibition Center, Pullman Club Coffee Shop, and the A. Philip Randolph Pullman Porter Museum. The Obama Presidential Center is 20 minutes away. Living directly across the street makes us accessible to guests.

FamilyValueParks

Superhost
The kitchen features wooden cabinetry and modern stainless steel appliances, including a refrigerator and a gas stove. Natural light filters through colorful curtains adorning the windows, complementing the inviting atmosphere. A functional layout allows for easy movement between the cooking and prep areas.
Apartment in Whiting
4.81 out of 5 average rating, 37 reviews

Water Gardens Getaway

Nestled in the heart Whiting's Water Garden's neighborhood, this cozy retreat blends charm, comfort, and convenience. Located in between Chicago and Indiana Dunes, it’s the perfect base for travelers of all kinds. Relax in a serene, thoughtfully designed space that offers comfortable sleeping arrangements, a fully-fenced-in backyard, in-building laundry, a spacious living space, a fully-equipped kitchen, and more!

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Superhost
A charming brown house is partially shaded by a large evergreen tree. The house features multiple windows, with one displaying white curtains. A set of steps leads to the front entry, which is framed by a small railing. Neighboring greenery adds to the home's appeal.
Home in Whiting
4.81 out of 5 average rating, 292 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

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Popular amenities for South Pole holiday rentals