Vacation rentals in Flossmoor

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Top-rated vacation rentals in Flossmoor

Guests agree: these vacation rentals 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, 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

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

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!

Superhost

Home in Beverly Shores

4.91 out of 5 average rating, 133 reviews

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.

Top guest favorite

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

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

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

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

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

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

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

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!

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What guests are saying

A Comfortable Stay While You are Away in Oak Park

4.85 out of 5 average rating, 68 reviews2 weeks ago

The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Home in Austin

What guests are saying

Spacious 2 Bed Apartment, Perfect Location

4.89 out of 5 average rating, 73 reviews3 weeks ago

This is a quirky, comfortable place. It’s full of great books, interesting decor and Chicago charm. The apartment is quite large, it’s on the ground floor and there is back door access to the alley from the kitchen. The kitchen was full of cookware and there was a gas stove. I appreciated the coffee pot and large tin of Costco coffee. There was also a great selection of teas as well as many interesting mugs to choose from.

Apartment in Lake View

What guests are saying

Sanctuary on the Ravine

5 out of 5 average rating, 28 reviews8 months ago

The Woodland house is truly incredible, with every detail thoughtfully designed for comfort, from the cozy bedrooms and soft linens to the inviting beds. The kitchen nook with a couch overlooking the ravine offers stunning views of nature, making it a picturesque spot to relax. The home exudes warmth and is perfect for unwinding in the spacious sunken living room or one of the multiple outdoor seating areas. Debra was an excellent host, providing all the amenities you could need. This home is a 10+, and you won't want to leave!

Home in Highland Park

What guests are saying

Loyola & Lake -3br/2bth close to the Lake & Loyola

4.95 out of 5 average rating, 80 reviews3 months ago

My friends and I stayed for my birthday weekend and were super happy with everything, the fireplace is especially nice for cold chicago winters! We only had trouble finding street parking Saturday night when we got back from our concert at 3am but that was expected. This will be my go-to place for groups from now on!

Apartment in East Rogers Park

What guests are saying

Creekside Getaway

4.9 out of 5 average rating, 40 reviews3 weeks ago

My wife and I loved the place. The wooded surroundings in the backyard with the stream running through or breathtaking. We would see on average anywhere from 15 to 20 deer every day. The house was even better than what the picture show. I never had to worry about being able to reach the owner. She was always accommodating and even offered us the opportunity to stay longer knowing that we were doing a longer-term, but we had already made arrangements to go somewhere else and couldn’t get out of it or we would’ve taken it.

Home in Merrillville

What guests are saying

Spacious Retreat with Beach Access

5 out of 5 average rating, 12 reviews1 month ago

⸻ “I had an exceptional stay at this Airbnb in Gary, Indiana! The host was fantastic—she communicated clearly and made sure I had everything I needed. She was so friendly and thorough, letting me know all the details about the home, how to get in, and how to use everything inside. The amenities were above and beyond what I expected. The space was incredibly comfortable, spotlessly clean, and the area near Lake Michigan was beautiful. The neighborhood was very quiet, safe, and enjoyable, which made the stay even better. I felt completely at home. The host also made it clear that if I needed anything, she was just a message away to assist. I enjoyed my stay tremendously and would absolutely recommend this space to anyone visiting. I would definitely come back a thousand times over!”

Home in Miller

What guests are saying

Relaxing1BR/1BAMini GolfFishingBands*Boating

5 out of 5 average rating, 8 reviews8 months ago

Chris is a phenomenal host. He lives a few minutes away from the RV and is very responsive. Two adults and 2 younger kids were very comfortable and had plenty of space to hangout in the RV. We did not take advantage of the activities at the site, but there was something nearly every hour over the weekend for guests (especially kids) to enjoy. If we are in the area, we would absolutely stay again!

Camper/RV in Portage

What guests are saying

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT!

4.96 out of 5 average rating, 50 reviews2 weeks ago

Beautiful home. We lived the sound system in the living room and the games (pool table, pinball, and arcade machine) in the basement. Property was conveniently connected to a beautiful walking path which also linked up with an awesome park. Last but not least, Ramon was readily available at a moment’s notice. He was a great host.

Home in Plainfield

What guests are saying

Tiny house in West Village Arts District

4.85 out of 5 average rating, 34 reviews3 months ago

Lisa was a great host and this is a great place. It's a small house, but worked great for what we needed it for and was close to our family that live in Evanston. It was also a great price. Additionally, there were games which was nice because we had our child with us. I would definitely recommend this place and I will be staying here again when we're in Evanston, hopefully Lisa's schedule will be open!

Guesthouse in Evanston

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