Vacation rentals in Chicago Heights

Apartment in Michigan City

A serene view of a beach landscape features gentle waves lapping at the shore under a clear sky. Lush green grass and a few trees frame the scene, highlighting the tranquil blue waters of the lake.

4.75 out of 5 average rating, 80 reviews

HotTub/Beachfront/Steam/Gameroom/Pets/MassageChair

Bordered by wilderness on 2 sides. Hot Tub(all year) Steam Room/Fireplace/ 3 Person jacuzzi/electric massage chair/ Pac-Man/ Area 51 Shooting game, Road Racing/Pinball/ Poker Machine. PlayStation 4. Bikes/Belgium Waffle/Snow Cone/ Popcorn/Free Soda Machine 4 flavors.3 minute walk on path to beach. 2 paddle boards/2 kayaks/tandem kayak. View wildlife at our feeding station. No children 2 to 8 years. Min age to rent=25. 4 person max all times including guest/Pets OK $60 fee. Massage extra cost

Cottage in Michiana Shores

A spiral staircase leads to an upper level, positioned beside a spacious kitchen island with seating for three. Recessed lighting and unique pendant lights illuminate the area, while a comfortable leather sofa is placed against a wall adorned with soft beach-themed artwork.

4.96 out of 5 average rating, 168 reviews

Prime Summer Days Still Open @ Birchwood Cottage!

With only a three night minimum stay in prime June, July & August on Lake Michigan's best beaches, THE BIRCHWOOD COTTAGE IN MICHIANA SHORES...where only good things happen & memories are made...is calling. Reviews tell our story & we are constantly upgrading to enhance you experience. We offer a slice of heaven just 75 minutes from downtown Chicago. Once settled in this cozy cottage you are just a short walk or even quicker bike ride to 5 beaches & everything you need is provided. BOOK IT NOW!

4.86 out of 5 average rating, 44 reviews

A large sleeping willow tree is featured next to a gravel path that leads to the cottage. The sunlight filters through the tree branches, casting gentle shadows on the ground. A white picket fence frames the scene, enhancing the tranquil outdoor setting.

Home in New Buffalo

Sleeping Willow Cozy Affordable Near Lake Michigan

Cottage style living at its best. Bright, cheery, cozy, and affordable. Flower gardens and a giant sleeping willow tree surround this charming home giving a relaxing outdoor experience. This house offers 3 bedrooms, a queen sofa sleeper, 1 full bath, a washer/dryer, wifi and Ruko TV. The kitchen has pots, pans, dishes, toaster, coffee pot, and dishwasher. Large deck on the rear of the property over looks the fenced-in fire pit area, perfect for making lasting memories with family and friends.

The image captures a serene beach scene at sunset, with soft sand and gentle waves. Tall grasses frame the foreground, leading the eye toward the calm water reflecting the warm hues of the setting sun and a lighthouse silhouette in the distance.

4.9 out of 5 average rating, 371 reviews

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

4.81 out of 5 average rating, 16 reviews

A spacious screened porch is furnished with comfortable blue seating and a decorative lamp. Natural light floods in through the expansive screened windows, creating a bright atmosphere. A small table is set with a bouquet, enhancing the inviting space. Views of the surrounding greenery are present.

Cottage in Grand Beach

Blocks To Beach Golf Tennis Park & Lake MI Sunsets

Your beach retreat awaits! Located on a quiet, no-outlet street steps to scenic Lake Mi lookouts, two community beaches, park, tennis, volleyball, basketball courts, 9-hole golf course with, village hall w/ ice cream & rentable event space overlooking beautiful golf course, nature trail, bike trail, and more. Home features a new AC and a spacious screened porch to enjoy the lake breezes. Minutes to breweries, dispensaries, wineries, casinos, farms, and more. House next door is also for rent!

4.91 out of 5 average rating, 133 reviews

Home in Beverly Shores

Dunes Vacation Rental

Near beach, casino, dunes and an easy drive to Chicago, Michigan and Notre Dame! Walkable to South Shore Train (Chicago). Features: Signature deck with gas grill, hot tub, outdoor shower, dining table, lounge area and fire pit. Luxury lower level with its own living area, tv, two bedrooms, three bathrooms, a bar and laundry. Upstairs features an open kitchen/dining room with gas fireplace, separate living room, full bathroom with dual shower heads, a master suite and two bunkbed rooms.

4.92 out of 5 average rating, 25 reviews

Apartment in New Buffalo

Charming 2BR/2BA Cottage with Full Kitchen & Patio

The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

Sandy dunes frame a serene beach scene, with gentle waves lapping at the shore under a clear blue sky. Grassy patches dot the landscape, stretching towards the horizon, where a lone figure can be seen enjoying the beach.

5 out of 5 average rating, 11 reviews

Villa Vesta-Lake Retreat

Escape to this charming 3-bedroom,2-bathroom house to get your VIP ticket to relaxation. Step inside the house and be greeted by an open concept living room. The kitchen is fully equipped for culinary adventures. Gather around the firepit for cozy evenings under the stars. Don't forget the hot tub; your personal time machine to a stress-free dimension. Your memories are waiting to be made here-beach is minutes away. See you soon- all those 5 star ratings last summer can’t be all wrong

Top guest favorite

Home in Grand Beach

5 out of 5 average rating, 110 reviews

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

Apartment in Logan Square

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

A serene view of the beach extends to the horizon, where gentle waves meet the sandy shore. Lush greenery frames the foreground, leading to a tranquil expanse of water under a partly cloudy sky.

4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

Perfect for Gatherings, Families, Birthdays, Group Outings: Enjoyment & Tranquility in Nature. Nestled on two acres of picturesque land, the property boasts a fully-equipped six-bedroom house. Conveniently located within a 5-minute drive to popular attractions such as the beach, casino, and outlet mall. Formerly a church, the house has been transformed into an inviting Airbnb rental, featuring a renovated interior, fire pit, gazebo, and many amenities.

Apartment in Michigan City

A sunset over Lake Michigan is captured through silhouetted trees. The sun's reflection glimmers on the water, creating a serene atmosphere. The peaceful scene is framed by a wooden railing, emphasizing the natural beauty of the lakeside setting.

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

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What guests are saying

"Sip, Sun & Fun: The Perfect Girls Beach Getaway!"

4.86 out of 5 average rating, 28 reviews7 months ago

My friends and I had a wonderful stay! The house is super cute and is close to the beach, shops, restaurants , the grocery store, and more! We were out of a few things but they responded immediately and dropped it off asap! We would definitely come back! Thank you!

Home in Michigan City

What guests are saying

Private Heated Pool and Pet Friendly!

4.77 out of 5 average rating, 13 reviews19 months ago

We enjoyed our stay with our son and his family. The house, yard and pool were perfect for our grandson and their two dogs. The neighborhood was very quiet and walkable. Our only possible concern was the lack of communication about the lawn being mowed and the pool being serviced on the Friday of our stay. It would have been nice to know so we could have had the dogs inside before people came into the yard.

Home in Michiana Shores

What guests are saying

Picture Perfect Lake House Steps from the Beach

4.98 out of 5 average rating, 61 reviews6 months ago

Absolutely perfect in every way. I have booked a (lakefront)fall retreat for a group of 12 ladies six years in a row. This home is by far the best equipped! From cozy blankets on hooks near the outdoor seating areas, cushions stored clean and dry inside so the outdoor seating could be used easily, and very high-quality large amount of beach chairs available, I have never seen such great amenities at a beach home! Mattresses are very high-quality and bedding was soft and luxurious! We loved every second of our weekend!

Home in Michigan City

What guests are saying

Lake Michigan Cottage Retreat

4.95 out of 5 average rating, 41 reviews5 months ago

OMG! We enjoyed our stay so much. Ryan's place made the perfect fall retreat. The surroundings were so peaceful. It was a short drive to Michigan City and New Buffalo. Lots of posh restaurants and shopping too. His place was clean and very well decorated. The beds were comfy. It felt like we were right at home. I would definitely book again.

Cottage in Michiana Shores

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Other great vacation rentals in Chicago Heights

Top guest favorite

A spacious living area features comfortable seating arranged around a central coffee table. A wall-mounted TV is visible above a white fireplace. Soft lighting is provided by a contemporary chandelier, and large windows are dressed with light curtains, enhancing the room's bright ambiance.

Home in Schaumburg

5 out of 5 average rating, 50 reviews

Great location-King beds-Kids playroom

5 out of 5 average rating, 5 reviews

A modern living space is presented with a white sofa and two accent chairs, arranged around a minimalist coffee table. A dining area is visible in the background, featuring a gold and glass table set with decorative items. Natural light filters in through large windows.

Home in Chicago

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

4.86 out of 5 average rating, 14 reviews

The open-concept kitchen features a large island with grey cabinetry and decorative tile accents. Colorful chairs surround a dining table, while a modern ceiling fan provides ventilation. The space includes multiple screens mounted on the wall for entertainment.

Home in Richton Park

Home away from home

An inground swimming pool features clear, blue water surrounded by a spacious deck area. Several lounge chairs are arranged alongside the pool, and pool floats are visible in the water. A secure fence encloses the area, providing safety and privacy.

4.92 out of 5 average rating, 64 reviews

Home near the lake with an inground pool

The outdoor space features a patio with seating arranged around a fire pit, surrounded by lush greenery. A grilling area is visible, along with a fence ensuring privacy. A light-colored, one-story home is situated in the background, framed by trees.