Vacation rentals in Olympia Fields

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Top-rated vacation rentals in Olympia Fields

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Top guest favorite

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

4.99 out of 5 average rating, 73 reviews

Lake retreat w/ unique dome near Indiana Dunes

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Guest favorite

Three kayaks, in shades of blue and green, rest on a grassy area near the Fox River. The gentle water flow can be seen in the background, with trees lining the riverbank, reflecting a peaceful outdoor setting.

Home in South Elgin

4.92 out of 5 average rating, 250 reviews

Riverfront rental with fun activity

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

Guest favorite

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

Apartment in West Lake View

4.94 out of 5 average rating, 175 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Top guest favorite

The living area features a white couch adorned with soft pillows and small accent chairs. Natural light brightens the space, complemented by a large flat-screen TV on a rustic console. Woven chairs provide additional seating around a light-colored coffee table.

Townhouse in Valparaiso

4.96 out of 5 average rating, 47 reviews

Cheerful, charming, super comfy 2BR 2Bath Condo

This cozy, lovely, & stylish getaway is the perfect go to spot for your visits to the many exquisite dunes & beaches of Indiana. Ten minutes from the National Park & its also amazing trails & preserves. Located in a quiet suburb of Valparaiso, just moments from the beloved university & the thriving downtown social hub flourishing with fun, food, & festivities. The South Shore train station is also close by for jaunts to Chicago & the plethora of Lake Michigan shoreline amenities.

Guest favorite

A serene outdoor seating area is illuminated by string lights, creating a soft, inviting glow. Comfortable seating is arranged around a small table, surrounded by lush greenery. The nearby river reflects the gentle light, enhancing the peaceful ambiance.

Home in Momence

4.96 out of 5 average rating, 166 reviews

Riverfront Oasis: Parks+ Kayaks+Relaxation Await!

Escape to this beautifully renovated 3-bedroom home with stunning Kankakee River views! Relax on the spacious deck or riverside patio while enjoying wildlife and peaceful scenery. Steps from Conrad Park and Island Park, you can stroll to local restaurants and shops. With all the comforts of home and just 50 miles from Chicago, it’s perfect for a getaway. Need more room? Book the cozy cabin next door tha hosts 4 more people! Your riverside retreat awaits—reserve your stay today!

Superhost

A welcoming living space is bathed in natural light, featuring large windows adorned with elegant curtains. A plush, tufted sofa with decorative pillows invites relaxation. Neutral walls complement the modern décor, which includes a sleek table and artwork, creating a harmonious atmosphere.

Home in Homewood

4.91 out of 5 average rating, 123 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favorite

A sandy path leads through tall grasses and dunes toward a tranquil beach and calm waters. Fluffy clouds float above, enhancing the serene landscape. Trees dot the scene, providing a natural frame to the tranquil view of the water and horizon.

Apartment in Miller

4.89 out of 5 average rating, 9 reviews

Miller Beach FairyForest Retreat

Escape to a whimsical retreat nestled atop the Indiana Dunes. Walk to the beach, only 3 blocks. Our mid-century modern three-bedroom apartment boasts a magical fairy forest theme, enchanting guests from the moment they arrive. Perched on a sand dune within the bio-swale ecosystem, each room offers treetop views. The true gem is our sprawling 400sqft screened porch, an elevated haven that immerses you in the tranquility of the woodland, evoking the sense you’re in a treehouse.

Superhost

The kitchen is equipped with modern stainless steel appliances, including a gas stove and a microwave. Light-colored cabinetry complements the granite countertops. Natural light filters through the window, illuminating the space and highlighting the well-organized layout.

Home in Chesterton

4.8 out of 5 average rating, 75 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

Welcome to our historically pet-friendly home, featuring chic and updated interior furnishings. 3 bedrooms | 2 bathrooms | 2 living rooms with Smart TVs and a porch Prime Location: Just a few minutes' walk to historic Chesterton downtown Proximity: 4 miles to Indiana Dunes National Park and the beach Fully Equipped Kitchen Family-Friendly: High chair and crib available Get ready for endless adventures at the sandy shores and tree-lined trails of Indiana Dunes National Park!

Guest favorite

A picturesque scene of a sandy beach is framed by gentle dunes and lush grasses. The waves gently lap at the shore, under a wide sky filled with a mix of clouds and sunlight, creating a serene coastal atmosphere.

Home in Porter

4.9 out of 5 average rating, 71 reviews

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Superhost

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.

Apartment in Logan Square

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!

Superhost

A serene view of a sandy path leading to a tranquil beach. Dunes covered in grass frame the scene, with a gentle stretch of Lake Michigan visible in the background. A few trees add greenery, and the sky is dotted with clouds, creating a peaceful atmosphere.

Home in Miller

4.93 out of 5 average rating, 137 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!