Vacation rentals in South Holland

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Top-rated vacation rentals in South Holland

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

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Top guest favorite
Guesthouse in Valparaiso
4.99 out of 5 average rating, 154 reviews

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

Guest favorite
Apartment in Hegewisch
4.9 out of 5 average rating, 250 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.

Guest favorite
Guesthouse in Merrillville
4.92 out of 5 average rating, 177 reviews

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Top guest favorite
Home in Whiting
4.9 out of 5 average rating, 103 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.

Guest favorite
A modern kitchen features a granite countertop with bar stools, accented by pendant lighting. In the background, a cozy seating area is visible with plush blue chairs. Wooden floors add warmth to the open layout, inviting interaction between the spaces.
Home in Burnham
4.88 out of 5 average rating, 34 reviews

Luxury Meets Comfort

Luxury Cozy Home ▪️High Speed Wi-Fi ▪️TVs in Every Bedroom ▪️Fireplace ▪️Streaming Apps ▪️Jacuzzi Tub ▪️Washer & Dryer ▪️King Size Bed ▪️Walk In Closet ▪️Full Size Bed ▪️Office Desk ▪️Queen Size Air Mattress (For Extra Guest) ▪️Fresh Linen ▪️Deep Cleaning ▪️Disinfecting of all surfaces ▪️Dishes,Eating Utensils,Pots and Pans ▪️Fenced In Yard ▪️Yard Furniture ▪️BBQ Grill Whether you’re visiting for business, family, or relaxation, this home offers a peaceful stay that feels like home.

Superhost
An open living space is highlighted by a stone fireplace and a large television mounted above it. A comfortable sectional sofa surrounds a round coffee table, while natural light fills the room through large windows. A dining area can be seen in the background.
Home in Homewood
5 out of 5 average rating, 16 reviews

Fore! Peace & Love @ Golf House

Welcome to "The Golf House"! Our 4-bed, 3-bath home sleeps 8 people comfortably and, features an open living space with a stunning golf course view, a full kitchen, and a huge deck. Enjoy natural sunlight or the stars through the skylight both in the master bedroom and bathroom. The home has hardwood floors, and TVs in each bedroom. Plus, a heated meditation room for relaxation. Ideal for families, women retreats, networking events etc. Experience luxury and tranquility right by the greens!

Guest favorite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Apartment in Homewood
4.92 out of 5 average rating, 114 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Guest favorite
A comfortable living room features a light-colored sofa and a cozy armchair, paired with a wooden coffee table. A large television is mounted on the wall, and plants are placed on the window sill. Geometric shelves add a decorative touch to the neutral-colored walls.
Home in Chicago
4.88 out of 5 average rating, 173 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favorite
Home in Lansing
4.97 out of 5 average rating, 34 reviews

Cozy 3BR Home Near Chicago

Relax in this cozy 3BR, 1BA home that sleeps up to 6, including a pullout couch. Enjoy a hammock, patio set, fire pit, ping pong table, grill, and dog tie-out. Located on a private half-acre lot with private parking. Just 11 mins from Hard Rock Casino (Gary, IN), 10 mins from Homewood Casino, and 29 mins from downtown Chicago. Near expressway, stores, forest preserves, and attractions like Indiana Beach, Six Flags, and Starved Rock. Basement not accessible. Contact host for issues.

Top guest favorite
Home in Munster
4.96 out of 5 average rating, 134 reviews

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Top guest favorite
Home in Munster
4.96 out of 5 average rating, 120 reviews

Your Quiet Oasis: Cozy & Private

Escape to this private 2-BR home, perfect for remote workers, cyclists & brewery fans! Enjoy a dedicated workspace with fast Wi-Fi (413 Mbps), a full kitchen, and a spacious, private backyard with a gas grill. This pet-friendly, single-level retreat is your convenient base for exploring nearby nature trails, 6 local breweries, and casinos. Comfortably fits small groups or families seeking a quiet getaway just 30 mins from Chicago.

Guest favorite
Home in South Holland
4.86 out of 5 average rating, 78 reviews

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

“What a great time we had, reconnecting and enjoying each other. We came back home in such a better place than we where when we left.” 🌹More than a stay — a private, immersive romantic experience crafted exclusively for adult couples who want something unforgettable, intimate, and truly one-of-a-kind.

Popular amenities for South Holland vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in South Holland?

    South Holland has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in South Holland?

    Experience the best of South Holland with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in South Holland?

    Yes! Work meets play with ease at over 20 vacation rentals in South Holland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in South Holland have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in South Holland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in South Holland have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in South Holland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in South Holland have wifi?

    Absolutely! We offer over 10 house rentals with wifi in South Holland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in South Holland have free parking?

    Absolutely! We offer over 10 house rentals with free parking in South Holland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in South Holland?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in South Holland

  • Total vacation rentals

    Explore 30 vacation rentals in South Holland

  • Nightly prices starting at

    South Holland vacation rentals start at G$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of South Holland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across South Holland rentals

  • 4.5 Average rating

    South Holland stays receive an average rating of 4.5 out of 5 from guests

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