Vacation rentals in Flossmoor

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Top-rated vacation rentals in Flossmoor

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Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Mar 5 – 12

$73 per night

Guest favorite

Apartment in Homewood

5.0 out of 5 average rating, 39 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 lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

Mar 12 – 19

$95 per night

Guest favorite

Cottage in Gary

4.96 out of 5 average rating, 113 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Nov 7 – 14

$123 per night

Superhost

Home in Homewood

4.91 out of 5 average rating, 35 reviews

Charming Homewood Away from Home

Keep it simple at this peaceful and centrally-located place. Cozy and Charming brick ranch nested on a quiet street. Minutes from the metra line taking you to downtown Chicago or visit the neighborhood shopping in downtown Homewood. No smoking and no parties. We are unable to accommodate a party of any size because of our agreement with our neighbors. Driveway is narrow. Limit 2 cars. No extra guest without notice. Extremely strict neighbors! We follow all cancellation rules.

Sep 7 – 14

$124 per night

Guest favorite

Apartment in Homewood

4.84 out of 5 average rating, 19 reviews

High-End Oasis Close to Fun

Escape to our inviting 2nd-floor High-End condo, just a short 37-minute drive from the vibrant heart of Downtown Chicago, Millennium Park, and Navy Pier. Immerse yourself in the charm of our neighborhood, surrounded by custom homes, golf clubs, and family-friendly entertainment. Many dining options all within a 2-minute drive or a quick Uber ride. Large balcony with seating for six and 2 minutes from the Metra Train Station for a fast trip to Chicago. Be one of our first guests!

Aug 21 – 28

$166 per night

Superhost

Home in Homewood

4.91 out of 5 average rating, 106 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💞

Oct 28 – Nov 4

$194 per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 238 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Nov 2 – 9

$112 per night

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 262 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Nov 2 – 9

$135 per night

Guest favorite

Townhouse in Country Club Hills

5.0 out of 5 average rating, 16 reviews

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Jul 10 – 17

$140 per night

Superhost

Home in Whiting

4.8 out of 5 average rating, 225 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

Jan 18 – 25

$80 per night

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 183 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Jul 28 – Aug 4

$112 per night

Guest favorite

Cabin in Griffith

4.91 out of 5 average rating, 152 reviews

Beautiful Rustic Cabin for Two!

Gorgeous newly renovated log cabin for two on a working homestead just minutes from Hard Rock Casino! Stop on in for one night or twenty nights! **EXCITING AUG 2023 update: We have replaced the futon with the BRAND NEW FULL SIZED BED pictured!

Jan 8 – 15

$74 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Flossmoor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Flossmoor

Guest favorite

Guest suite in Homewood

4.96 out of 5 average rating, 54 reviews

Cozy/Romantic Game Room Suite w/Outdoor Hot Tub

Nov 15 – 22

$155 per night

Guest favorite

Home in Lansing

4.84 out of 5 average rating, 64 reviews

The Walter Experience

Aug 11 – 18

$87 per night

Guest favorite

Home in Olympia Fields

5.0 out of 5 average rating, 9 reviews

Exquisite Getaway Home

Sep 3 – 10

$234 per night

Superhost

Home in Homewood

4.95 out of 5 average rating, 19 reviews

Our Homewood Home

Nov 23 – 30

$284 per night

Guest favorite

Home in Munster

4.97 out of 5 average rating, 33 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Oct 14 – 21

$116 per night

Guest favorite

Home in Oak Forest

4.91 out of 5 average rating, 75 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

Jun 6 – 13

$238 per night

Guest favorite

Home in Matteson

4.93 out of 5 average rating, 15 reviews

Soulful 5-Bedroom Home with Indoor Fireplace

Feb 19 – 26

$244 per night

Guest favorite

Home in Chicago

4.92 out of 5 average rating, 85 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Feb 27 – Mar 6

$99 per night

Show all

Quick stats about vacation rentals in Flossmoor

Total rentals
10 properties
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
210 reviews

Frequently Asked Questions

Do house rentals in Flossmoor have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Flossmoor. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Flossmoor?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Flossmoor have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Flossmoor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Flossmoor have free parking?
Absolutely! We offer over 10 house rentals with free parking in Flossmoor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Flossmoor?
Flossmoor has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Flossmoor?
Yes! Work meets play with ease at over 10 vacation rentals in Flossmoor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Flossmoor have wifi?
Absolutely! We offer over 10 house rentals with wifi in Flossmoor. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Flossmoor?
Four-legged friends are welcome in Flossmoor. Choose from more than 10 vacation rentals for guests traveling with pets.

Vacation rentals in Flossmoor

Top-rated vacation rentals in Flossmoor

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Flossmoor vacation rentals

Other great vacation rentals in Flossmoor

Guest suite in Homewood

Home in Lansing

Home in Olympia Fields

Home in Homewood

Home in Munster

Home in Oak Forest

Home in Matteson

Home in Chicago

Quick stats about vacation rentals in Flossmoor

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Flossmoor have air conditioning?

What are the most popular amenities for House Rentals in Flossmoor?

Do house rentals in Flossmoor have a kitchen?

Do house rentals in Flossmoor have free parking?

Are there family-friendly vacation rentals in Flossmoor?

Are there vacation rentals with a dedicated workspace in Flossmoor?

Do house rentals in Flossmoor have wifi?

Are there pet-friendly vacation rentals in Flossmoor?

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