House holiday rentals in Homewood

4.96 out of 5 average rating, 108 reviews

New sauna, steps from beach and National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

4.77 out of 5 average rating, 124 reviews

A spacious living area features a large sectional sofa adorned with decorative pillows. A round coffee table sits in front of the couch, accompanied by carefully arranged vases. Natural light filters in through large windows, illuminating the stone accent wall.

Home in Hammond

Spacious home 28 miles from Downtown Chicago

This lovely 4B/2B home features an open concept floor plan. Property features a living/dining room and kitchen with a Keurig for your morning coffee. This home is located close to I80-94 making it convenient for guests to explore the area! Our guests have access to the entire home. This property is located less than 30 minutes from downtown Chicago and Schererville, IN and less than an hour from Orland Park and Oak Brook Mall where there are plenty of restaurants and stores for shopping.

4.92 out of 5 average rating, 143 reviews

Home in Whiting

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.

4.96 out of 5 average rating, 140 reviews

A modern farmhouse is showcased, featuring a covered front porch with comfortable seating. Lush greenery surrounds the entrance and a small outdoor seating area with a table and chairs is visible. The structure is complemented by large windows that invite natural light.

Home in Crown Point

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

A welcoming living area is highlighted by a navy blue sofa positioned beside a decorative plant. A round coffee table rests atop a patterned area rug featuring shades of blue and yellow. Light-colored walls and large windows enhance the brightness of the space.

4.87 out of 5 average rating, 106 reviews

Charming Homewood Away from Home

Keep it simple at this cozy, charming brick ranch tucked away on a quiet, friendly street. Just minutes from the Metra line for an easy ride into downtown Chicago, and close to all the great local shopping and dining in downtown Homewood. House Guidelines: • No smoking, no parties, no large gatherings • Be mindful of neighbors • Narrow driveway, limit 2 cars • No extra guests without notice • Pets are welcome, but must be added to your reservation • We have a moderate cancellation policy

4.97 out of 5 average rating, 336 reviews

The living room features a spacious brown sectional sofa facing a coffee table, with a wall-mounted artwork above. A ceiling fan and natural light enhance the open space, which transitions to a dining area visible in the background, creating a welcoming and cozy atmosphere.

Home in Manteno

Two king beds with 3 bedroom 2 bath

4 minutes from I-57 expressway. This is a three bedroom two full bath townhome with a 2 car attached garage. King bed & 55' smart tv in the master bedroom. The Master bedroom also has a full bathroom with complimentary body wash, shampoo & conditioner. 2nd bedroom has a king size bed with king size hotel pillows. 3rd bedroom has queen bed with 55" smart tv. In closet you will find a deluxe queen size air bed with extra pillows & linens. Patio has table & chairs & charcoal grill.

4.95 out of 5 average rating, 202 reviews

Home in Whiting

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

*REQUIRED* ✅ Will you bring a pet? ✅ Have you read and agree to all rules? 🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilets

4.96 out of 5 average rating, 143 reviews

A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.

Home in Munster

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.

A cozy living area features a navy blue sectional sofa adorned with colorful cushions. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. A flat-screen TV is positioned on a mid-century style console, next to a warm brick fireplace.

4.73 out of 5 average rating, 164 reviews

Cottage Feel 2 bedroom Home!

Welcome to your home away from home! Relax and unwind in this cozy, peaceful space that’s thoughtfully maintained to make your stay comfortable and stress-free. While this isn’t a luxury home, it’s clean, inviting, and equipped with everything you need for a pleasant visit. Conveniently located in the south suburbs of Illinois, you’ll be just minutes from great restaurants, shopping, parks, entertainment, and major highways.

4.96 out of 5 average rating, 277 reviews

Double doors open to a bright living area featuring a leather sofa and a light-colored armchair. A coffee table is placed on a soft area rug, while lamps provide soft illumination. A ceiling fan hangs above, and large windows allow natural light to fill the space.

Home in Manteno

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

4.96 out of 5 average rating, 135 reviews

A spacious living area features a light-colored sectional sofa adorned with soft pillows, positioned beside a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through a window, complemented by dark curtains. A potted plant and lamps provide additional light.

Home in Munster

Quiet Oasis: Cozy, Private, Fenced Yard & Office

Private, pet-friendly 2-bedroom single-level retreat near Chicago, ideal for 4 guests + infant. Features a dedicated remote workspace with 413 Mbps Wi-Fi, fully equipped kitchen, and a spacious private backyard with a gas grill. Perfect for remote workers, cycling enthusiasts, and brewery lovers, offering easy access to nature trails, 6 local breweries, and casinos. Enjoy a quiet escape just 30 minutes from the city.

4.94 out of 5 average rating, 122 reviews

A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.

Home in Worth

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

Popular amenities for Homewood house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area features a heated in-ground pool surrounded by lush greenery. Lounge chairs with red umbrellas provide shaded seating. Colorful flowers and tropical plants enhance the peaceful outdoor setting, creating an inviting place for relaxation.

4.94 out of 5 average rating, 158 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

4.92 out of 5 average rating, 25 reviews

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

Munster hide away

4.82 out of 5 average rating, 96 reviews

A panoramic view of a spacious property is showcased, featuring a stone exterior and large windows. Green grass and various trees surround the house, along with landscaped flower beds. The setting offers an inviting outdoor space, ideal for gatherings.

Home in Cedar Lake

Beautiful Home Oasis

4.86 out of 5 average rating, 21 reviews

Home in Porter

After-Dune Delight! Large Home w/ Heated Pool

4.89 out of 5 average rating, 36 reviews

Home in Bridgeport

PRIME 2BD Designer Retreat & Pool |Parking| Patio

4.71 out of 5 average rating, 62 reviews

Home in West Loop

Chic Fulton Market Oasis + Curated Comfort & Style

An in-ground pool is surrounded by lush greenery and outdoor seating areas. Sun loungers are positioned near the clear blue water, and a shaded patio area features red umbrellas. The pool area is well-maintained, inviting relaxation after a day by the beach.

4.93 out of 5 average rating, 42 reviews

Pool & Beach Haven-private pool, steps to beach!

A large swimming pool is surrounded by a concrete deck and a wooden fence. Lush greenery is present in the background, adding to the serene atmosphere. A few lounge chairs are placed nearby, creating a space for relaxation.

4.63 out of 5 average rating, 38 reviews

Cheerful 4 bedroom 2 king size beds, 2 queen size

Weekly house rentals

A cozy living room features a light gray sectional sofa adorned with decorative pillows. A minimalist side table holds a small potted plant. Natural light enters through the large windows, illuminating the space and highlighting the soft area rug beneath.

4.92 out of 5 average rating, 24 reviews

Spruce Sanctuary

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.

4.97 out of 5 average rating, 31 reviews

Fore! Peace & Love @ Golf House

An open living area features a light grey sectional sofa complemented by a wooden accent table. Natural light fills the space through large windows, illuminating a neutral area rug on the wooden floor. A dining table with chairs occupies the background, along with a wall-mounted television.

4.9 out of 5 average rating, 41 reviews

4BR/2BA Family Home + Fenced Backyard

4.91 out of 5 average rating, 35 reviews

A spacious living area is furnished with a large gray sectional sofa, accented by a black ottoman in the center. Natural light filters through the vertical blinds of two windows, while a round mirror adds a decorative touch to the wall.

Home in Tinley Park

Luxury Townhome in Tinley Park Near Shops & Train

An open-concept living area features a spacious layout with cozy sectional seating and a light area rug. A dining table is visible in the background, complemented by modern pendant lighting. The kitchen boasts a large island with bar stools and stainless steel appliances, with natural light streaming in through large windows.

4.94 out of 5 average rating, 47 reviews

Modern Charming Home w/Pergola & games

A spacious living area features a comfortable sofa and two accent chairs. A wooden coffee table sits centrally on a soft area rug, while a dining space is visible in the background. Natural light filters through large windows, enhancing the bright, neutral color palette.

4.86 out of 5 average rating, 43 reviews

Suburban Haven: Cozy Escape with a Touch of Luxury

4.83 out of 5 average rating, 77 reviews

Home in Matteson

5-BR Home: 1.5-Acre Yard & Fire Pit

The living area features a grey sofa and loveseat, both adorned with decorative pillows. An orange throw blanket rests on the sofa. A rectangular coffee table sits on a patterned rug, with a lamp and small decor items placed on it. Bright orange and grey curtains frame the windows.

4.87 out of 5 average rating, 83 reviews

Cozy & Lavish 2B/1B in Homewood!

Private house rentals

Home in Country Club Hills

Cul De Sac Jacuzzi home | Near Chicago

4.87 out of 5 average rating, 39 reviews

4.84 out of 5 average rating, 88 reviews

Home in South Holland

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

4.91 out of 5 average rating, 11 reviews

Home in New Lenox

Relaxing Home Away From Home

4.95 out of 5 average rating, 20 reviews

A living room is shown, featuring a cozy orange couch positioned in front of a glass coffee table. A decorative tray with items is placed atop the table. Reflections from a large mirror adorn the wall, and a view into the kitchen is visible in the background.

Home in Richton Park

Home in Richton Park, Illinois

5.0 out of 5 average rating, 52 reviews

A spacious wooden deck descends to a fenced backyard featuring a well-maintained lawn. The outdoor seating area includes a large table set for meals, with views of the lake and surrounding greenery visible beyond the yard.

Home in Cedar Lake

Lakeside Loft

4.84 out of 5 average rating, 45 reviews

Home in Tinley Park

Cozy/Private 3 BR nestled on an acre of Serenity

4.71 out of 5 average rating, 48 reviews

The exterior of a single-story house is shown, featuring a beige vinyl siding and a distinctive peaked roof. A welcoming entryway is highlighted by a glass-paneled door. The front yard includes a well-maintained flower bed with various plants and a pathway leading to the entrance.

Home in Riverdale

Cozy 3Bed Home in Friendly South Chicago Suburbs