Holiday houses in Oak Forest

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Top-rated holiday rentals in Oak Forest

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

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.

5 – 12 Mar

$1,107 AUD total

Guest favourite

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!

12 – 19 Mar

$1,373 AUD total

Guest favourite

Home in Oak Forest

4.92 out of 5 average rating, 51 reviews

My Prima Karina 4bd 2ba in Chicago Suburbs

Beautifully appointed 4bd 2bth nestled in a quiet, tree-lined neighborhood but close to it all! Minutes from Downtown Chicago come home to smart TVs in every bedroom, super hi-speed wifi, elegant fully equipped kitchen includes air fryer, blender, cast iron skillet, oils/spices and coffee/tea station. Dedicated workspace, parking and laundry on site. 3 minute drive to Metra station & highway access into Downtown Chicago (30 mins) close to vast shopping and great dining options!

28 Sept – 5 Oct

$3,023 AUD total

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.

7 – 14 Sept

$1,833 AUD total

Guest favourite

Guest suite in Orland Park

4.99 out of 5 average rating, 70 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

25 May – 1 June

$1,413 AUD total

Guest favourite

Home in Robbins

4.97 out of 5 average rating, 36 reviews

Comfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW

Summer dates are almost gone! We'd love to host you! Clean 1800+sq SF suburban home < 35 mins away from dwtwn Chgo. Near expressways (294, I-57) & highways, train station, restaurants & major retailers + full-service grocery store <5 mins. Becvar & Son Funeral Home, Moraine Valley College (4 miles), St. Xavier (5 miles). This multi-generational family home was filled w/ love & memories until '22. Reservation holder must live 50 miles outside of the property location.

3 – 10 Sept

$1,597 AUD total

Guest favourite

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

2 – 9 Nov

$1,402 AUD total

Guest favourite

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.

2 – 9 Nov

$1,816 AUD total

Guest favourite

Home in Chicago Ridge

4.85 out of 5 average rating, 48 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

12 – 19 Feb

$1,673 AUD total

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

18 – 25 Jan

$1,315 AUD total

Guest favourite

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.

28 July – 4 Aug

$1,625 AUD total

Guest favourite

Home in Oak Forest

4.91 out of 5 average rating, 75 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

Beautifully updated 3 bdrm 2 ba home in Oak Forest! Upgraded kitchen cabinets with stainless steel appliances with a large eat-in kitchen. 2 full baths, plenty of room for entertaining in family rooms. A vending machine conveniently located downstairs. Majestic private backyard.

6 – 13 June

$3,331 AUD total