Find Vacation Rentals in Oak Park

Highlights Oak Park

  • Vacation rentals
  • Peaceful getaways
  • Large selection of outdoor activities
  • International food
  • Ancient architecture
  • Historical landmarks
  • Natural features

Best Vacation Rentals in Oak Park

Guests agree: these stays are highly rated for location, cleanliness, and more.
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Oak Park, Cook County
Vacation Rental • 1195 ft² • 2 Bedrooms
5.0
(20 reviews)
Enjoy your stay in Oak Park at this prairie architecture themed apartment. It is located in the lower level of a new construction home. As you enter, you will be blown away by the soaring 9-10' ceilings and open & airy layout. The two bedroom apartment has one bedroom with a queen sized bed and another with two twin beds. Living room features a futon style couch for extra sleeping capacity. Five people can be accommodated in the apartment. The heart of the apartment is the vast living room/dining room area. Enjoy meals at the dining room table, which seats eight. Relax in the living roo...
from $164 / night
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Oak Park, Cook County
Vacation Rental • 1593 ft² • 2 Bedrooms
5.0
(20 reviews)
Welcome to your most cozy and private, quiet respite place. This second floor luxury apartment is decked out to the 9's. 3 private bedrooms and the living areas are very spacious, with the flow designed to allow private getaway spaces. One bath is very large and stocked with all you need. Very large gourmet kitchen with all cook and dinner ware. Owner lives on first and lower level floors - you won't even know you are staying in an apartment - feels like a home and sound proof. No shoes to be worn in the home, so bring your slippers. I have received over 100 - 5-Star reviews for the space d...
from $161 / night
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Oak Park, Cook County
Vacation Rental • 1195 ft² • 2 Bedrooms
3.9
(13 reviews)
The first floor flat is a large bright 2 bedroom apartment with a new kitchen featuring Stainless Steel Fagor appliances, granite counter tops and maple flooring. We have hardwood floors in the Living Room & Dining Room. Two carpeted bedrooms with a queen in one and Full in the second. LvRm with couch & love seat and Futon in game room creates even more space. The apartment is fully furnished including all kitchen items with a piano for your use, ATT U-verse TV, internet and phone. Extra space is provided inside with a Playroom in the full basement with a TV , Foosball table and a l...
from $154 / night

Prices and availability

Vacation rental prices in Oak Park

$267for 3 Dec - 10 Dec
$325 annual average
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Average price per week

Vacation rentals availability in Oak Park

36%for 3 Dec - 10 Dec
48% annual average
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Percentage of available rentals

Vacation rentals in Oak Park

Vacation rentals locations

Oak Park is a quiet suburb located next to the bustling city of Chicago. While Chicago may be the best vacation destination for most travelers visiting Illinois, the village of Oak Park can be a perfect getaway, thanks to its numerous attractions. The village has outstanding museums and architectural heritage to explore for history and architectural buffs. And the good thing is, you don't have to struggle to look for an ideal vacation rental. You can browse through our site and compare several rental properties to find one that suits your needs. Most vacation rentals in Oak Park are located near attraction sites to make it easier to visit them.

Vacation rentals for everyone

If you're visiting Oak Park alone, with family or friends, the village has a rental property to accommodate you. Visit the city for a weekend getaway with friends and find a rental property that can accommodate groups of more than ten people. On the other hand, if you visit for a family retreat, you'll find a perfect vacation rental that's suitable for your kids and pets. Luckily, most rentals have fully-equipped bedrooms, living rooms, and kitchens. In addition, you will enjoy a variety of features and amenities such as a balcony, yard, washing machine, TV, internet, and parking.

Vacations in Oak Park

The area and getting around

A quiet suburb with exciting attractions

Oak Park is located on the western side of Chicago and sits between West Roosevelt Road and West North Avenue. This quiet suburb is best known as a residential area for iconic people such as Frank Lloyd Wright, Ernest Hemingway, and Betty White. You will enjoy exploring their contributions to the popularity of Oak Park. For example, you can explore various architectures by Frank Lloyd Wright dating back to the 1880s. Still, you can explore the Hemingway Museum and gain a few insights into the famous author's life.

International food and unique local activities

Travelers in Chicago may visit this quiet village to escape the hustle and bustle of the big city. With over 52,000 residents in Oak City, you're likely to find several unique activities. Whether you want to go shopping, eat out or spend evenings in lively entertainment joints, there's always something to do. The village has several restaurants that have unique specialties. You can enjoy American food, French dishes, Mexican food, and local dishes. Visit the old buildings that serve as shops, stores, and pubs. Explore the building and find unique items you can buy as souvenirs or gifts.

Travelers and outdoor activities

Oak Park for architecture and history enthusiasts

One thing that makes Oak Park stand out is its architectural heritage, including various pristine buildings by Frank Lloyd Wright. You will find his picturesque home and studio where he lived with his wife. Still, you can explore other buildings he designed, including the Unity Temple and several residences. You can also visit the Hemingway Museum that served as the birthplace of this iconic author. The Victorian building was built by Hemingway's maternal grandparents in 1890 and has been restored to its original appearance. Explore the family's furniture, photos, and the second-floor bedroom where Hemingway was born.

Oak Park natural features for recreations

Despite being a small suburb, Oak Park has fascinating natural features you can explore with family and friends. Venture out of your vacation rental and head to various parks, such as the Grand Illinois Trail that cuts through the village along Augusta Boulevard. The site is ideal for travelers interested in biking and trailing. You can visit Grant Park and Lincoln Park near Lake Michigan for family-friendly parks. Enjoy exploring the beautiful green spaces, tree-lined lawns, and beaches. You can also head onto the lake for various water activities.

Did you know that Oak Park has the largest number of Frank Lloyd Wright's buildings across the world? His house and studio serve as national historical landmarks today.

Top 5 travel tips for Oak Park

1. Oak Park Conservatory

Would you like to be one with nature while in Oak Park? Visit Oak Park Conservatory, a garden founded in 1914 and features a collection of plant species. The current structure was rescued in the 1970s after several years of neglect. The site has over 20,000 plants, including tropical, desert, and Mediterranean species. In addition, you'll find a pond that's home to animals like turtles, koi, and goldfish.

2. Oak Park Farmer's Market

When you visit Oak Park from May to October, you can visit a half a century old farmers' market. The market is held in Pilgrim Church's parking lot at 460 Lake Street. You can buy fresh local produce to prepare meals at your rental property when you visit the market. For example, you'll find fresh fruits, vegetables, honey, cheese, jams, jellies, salsas, and baked goods.

3. Columbus Park

If you're looking for a public park to spend a day with your family or friends in Oak Park, visit Columbus Park. The park is over 135 acres and features Jens Jensen architecture and his Prairie School approach. You will enjoy exploring the natural beauty and native plants that make the park a perfect place to interact with nature. In addition, you can explore Jensen's stone paths, waterfalls, and the Council Ring that will help you relate with Native American traditions.

4. Wonder Works Children's Museum

Treat your children to a visit to Wonder Works Children's Museum, where they can enjoy several indoor and outdoor activities. The museum is ideal for kids of up to eight years who are energetic and curious to explore and learn. Children can enjoy climbing, building, and playing musical instruments. Other exciting games include solving puzzles and role-playing in various situations like doctor visits and shopping. Parents and caregivers can join in and enjoy several live events, spooky fun, and Storytime.

5. Downtown Oak Park

Visit downtown Oak Park and explore the commercial district with bustling places like Lake Street and Oak Park Avenue. The place is ideal for sightseeing. You can walk along tree-lined streets and local businesses like restaurants and pubs. Visit a nearby restaurant and enjoy a variety of dining options like pizza, sushi, BBQ, vegetarian, among other international dishes. Still, you can visit entertainment centers such as the seven-screen Lake Theater where you can watch a movie with friends.

FAQs: Vacation Rentals in Oak Park

What was the average price for a vacation rental in Oak Park last year?

Oak Park is one of the cheapest cities in the USA. The price for a vacation rental is around $332 per night.

What time of year offers, on average, the best vacation rental prices in Oak Park?

]If you are looking to get the most out of your money, the cheapest months to visit Oak Park are April ($286 the average per night for accommodation), March ($292), and May ($307).

When does the price of vacation rentals in Oak Park go up the most?

When it comes to looking for a vacation rental in Oak Park, the months when it is most expensive are, in order of highest to lowest, January, February and September, with average prices per night of $394, $367, and $365, respectively.

Is Oak Park a good location for a last-minute getaway?

In order to not have problems finding accommodation in Oak Park, it is necessary to think ahead as 67% of rentals are usually booked, according to last year's data.

What are the best months for a spontaneous getaway?

The months that offer the most accommodation options are, on average, January (with an availability of 52%), June (50%), and May (50%), according to the trends observed in the prior year.

When are there fewer vacation rental options available in Oak Park?

The months with the lowest properties available in Oak Park are, in order, September, April, and October with respective average availability figures of 5%, 16%, and 21%, based on the previous year. During this period, the availability is very low (14%). It is therefore preferable to reserve far in advance.

Are there many vacation rentals in Oak Park?

We have 20 properties for you in Oak Park, provided by our 3 local and international partners.

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