Holiday houses in Countryside

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Top-rated holiday rentals in Countryside

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Guest favourite

Loft in Forest Park

4.96 out of 5 average rating, 463 reviews

Walk to Oak Park from a Bright Madison Street Loft

Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.

9–16 Dec

$253 NZD per night

Guest favourite

Guest suite in Wood Dale

4.9 out of 5 average rating, 430 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

16–23 Jul

$227 NZD per night

Guest favourite

Home in Berwyn

4.92 out of 5 average rating, 240 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

8–15 Sep

$175 NZD per night

Guest favourite

Apartment in Berwyn

4.99 out of 5 average rating, 254 reviews

Berwyn Betty Apartment

New to the market- this completely renovated apartment sits atop our Bath and Body workshop. Our small business began in our home 8 years ago and in 2016 it became too big to stay there. We bought this run down corner store building that sits on a double lot on a neighborhood street in south Berwyn. Over the next year, we completely renovated the building. The first floor is the home to our e-commerce business. The second floor was built with the traveller's needs in mind.

20–27 Jan

$311 NZD per night

Guest favourite

Guest suite in Carol Stream

4.94 out of 5 average rating, 285 reviews

Hot Tub, Pool Table, Bar, fishing & Kayak on Lake!

Very large entire basement w/3 separate areas. Great for friends traveling together! (entrance thru main part of house Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! *entrance thru the main part of house. This is just for the basement apartment but you have complete privacy down there. Read through entire listing & look through pictures to see all our home has to offer!

24 Nov – 1 Dec

$247 NZD per night

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

19–26 Feb

$182 NZD per night

Guest favourite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 244 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

7–14 Mar

$213 NZD per night

Guest favourite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

23–30 Apr

$254 NZD per night

Guest favourite

Apartment in Forest Park

5.0 out of 5 average rating, 222 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

24–31 Oct

$221 NZD per night

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 103 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

28 Dec – 4 Jan

$205 NZD per night

Guest favourite

Apartment in Naperville

4.87 out of 5 average rating, 147 reviews

Comforts of home in downtown Naperville

Cozy 1 bedroom garden level apartment located in downtown Naperville. Short walking distance to great shopping and many fine restaurants. Also short walking distance to train which goes directly to Chicago. Parking is available for 1 car in driveway. Professionally cleaned after every guest visit, as well as free cleaning offered for stays of two weeks or longer.

8–13 May

$224 NZD per night

Guest favourite

Home in Justice

4.95 out of 5 average rating, 193 reviews

3 Kings | 1 Queen | 1 Full | 3 air beds | 2 Pack 'n Plays No charge for cleaning, extra people, or any other hidden fees. 20% weekly discount applied to 7+ nights. Minutes to I-294, I-55. 30 mins to Chicago & O'Hare Airport. 20 mins to Midway Airport. 5 mins to Cook County’s forest preserves w/ bike, walking, and horse trails.

14–21 Nov

$835 NZD per night