Best Vacation Homes in Cheltenham
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Cheltenham Luxury Rentals
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Cheltenham Pet Friendly Vacation Rentals
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Cheltenham Large Vacation Homes
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Why Choose Rent By Owner for your Cheltenham Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Cheltenham Vacation Rentals
Where are the best neighborhoods to stay in Cheltenham?
When choosing a neighborhood to stay in within Cheltenham, Chicago, Illinois, you’ll find a variety of charming areas that offer unique local flavors and convenient access to the city's attractions. Exploring neighborhoods in this vibrant part of Chicago allows you to experience the diverse culture, welcoming community, and excellent amenities that make your visit memorable. Whether you're seeking a lively atmosphere or a peaceful retreat, the neighborhoods here provide the perfect backdrop for your stay, ensuring a seamless and enjoyable experience during your time in this dynamic city.
South Chicago
In this part of the city, you’ll find a welcoming community with easy access to local amenities and parks, making it an ideal spot for those seeking convenience and comfort. The area offers various options for choosing your perfect vacation rental that combines affordability with proximity to the region’s highlights.
View 73+ Rentals in South ChicagoBest Times to Visit Cheltenham
When should you plan your Vacation Rentals stay?
Choosing the right time to visit can enhance your experience here, allowing you to enjoy the region’s best weather and events while securing the most convenient dates for your stay.
Peak Season Highlights
Spring (March to May)
During spring, you'll experience mild weather and blooming landscapes, making it an ideal time to explore the area and enjoy your stay in this destination.
Fall (September to November)
Autumn offers comfortable temperatures and vibrant foliage, perfect for outdoor activities and enjoying the region’s scenic beauty during your visit.
Off-Season Highlights
Summer (June to August)
While summer sees warm weather and plenty of events, it’s also the busiest season. Planning your stay during this time can help you find more tranquility in your vacation rentals here.
Winter (December to February)
The winter months bring cooler temperatures and fewer crowds, offering a quiet retreat and cozy atmosphere in your chosen vacation rentals during this off-peak season.
Weekly Weather Forecast for Cheltenham
How to Book Your Cheltenham Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Cheltenham
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or backyard space for relaxing or dining al fresco.
- Take advantage of outdoor seating areas that provide comfort and scenic views of the surrounding greenery.
- Make use of on-site barbecue grills to prepare meals during your stay in this welcoming destination.
- Benefit from well-maintained gardens or landscaped yards that add to the outdoor ambiance.
- Utilize designated outdoor parking spaces for added convenience during your visit.
- Experience the tranquility of a shared outdoor space, perfect for unwinding after exploring the area.
- Look for properties with fire pits or outdoor fireplaces to enjoy cozy evenings under the stars.
Top Attractions Around Cheltenham
What attractions are nearby?
Nearby, you can enjoy a variety of activities in the region, from exploring local parks and cultural sites to discovering dining and entertainment options that make for a memorable stay here.
Family Activities
- Lincoln Park Zoo: Spend a day exploring this free, family-friendly zoo nestled within a scenic park setting, offering an engaging experience for children and adults alike.
- Chicago Children's Museum: Discover interactive exhibits and hands-on activities here that inspire learning and fun for kids of all ages in the heart of the city.
- Maggie Daley Park: Enjoy outdoor play on innovative playgrounds, lush gardens, and ice skating rinks in this vibrant park located conveniently downtown.
- Shedd Aquarium: Dive into aquatic adventures with diverse marine life exhibits that captivate young explorers and provide educational entertainment for your family.
Adult Activities
- Millennium Park: You can enjoy the stunning public art installations and modern architecture that make Millennium Park a must-visit attraction in this vibrant area.
- The Art Institute of Chicago: Immerse yourself in world-class artwork and exhibitions at one of the world's oldest and largest art museums, located conveniently downtown.
- Navy Pier: Experience waterfront attractions, scenic boat rides, and lively entertainment that capture the essence of this iconic Chicago destination.
- Magnificent Mile: Shop at high-end boutiques or dine at renowned restaurants along this famous shopping district, perfect for a stylish day out.
Other Places to Stay in Cheltenham, IL
Cheltenham Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover hidden gems and popular spots in the area to truly experience what makes this destination special.
- Plan Your Transportation: Arrange your transportation options in advance to easily navigate the region and maximize your sightseeing opportunities.
- Choose the Ideal Accommodation: Select a well-located vacation rental that offers comfort and convenience, ensuring a relaxed stay here.
- Embrace Local Cuisine: Sample the regional flavors by visiting nearby eateries or preparing meals in your rental to enjoy authentic local dishes.
Transportation Options
- Chicago Transit Authority (CTA) Trains: The CTA provides extensive train services that make getting around the area quick and convenient for exploring this vibrant destination.
- Bus Services: Local bus routes offer flexible transportation options, connecting you to key spots within the city and nearby neighborhoods with ease.
- Taxis and Rideshare Services: Taxis and ride-hailing apps like Uber and Lyft are readily available, providing a comfortable way to travel directly from your vacation rental.
- Bike Rentals: Cycling is a popular option here, with numerous bike rental stations allowing you to enjoy the scenic routes at your own pace.
Local Customs Options
- Respect for Local Traditions: When visiting here, you’ll find that embracing local customs is highly valued, reflecting the community's appreciation for its unique cultural heritage.
- Greeting Etiquette: A friendly nod or handshake is customary when meeting new locals, helping you establish a warm connection in this welcoming region.
- Dining Customs: Taking time to enjoy meals together and observing proper table manners are an important part of social interactions in this area’s vibrant culinary scene.
- Celebration Practices: Participating in local festivals and events allows you to experience authentic traditions that are cherished here, enriching your overall visit.
Frequently Asked Questions About Cheltenham?
1. What are the top vacation rentals in Cheltenham?
There are a lot of options in Cheltenham. If you plan on staying in the Cheltenham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cheltenham:
- University of Chicago Condo-Upgraded and Spacious w/Parking
- Charming 3-bedroom apartment with AC, WiFi in phenomenal Chicago
- Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
- Gorgeous 4BDR in Chicago/15mins from DWTN Brand New!
- Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago
- Luxury Chic Condo Near Hot Attractions w/FastWi-Fi
- Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
- Beautiful 4 bedroom 2 bathroom apartment near everything
- Luxurious 3 Bedroom Getaway
- Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
2. Which vacation homes in Cheltenham are best for families?
If you are looking for a family-friendly vacation home in Cheltenham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cheltenham:
3. How many Rentbyowner vacation rentals are available in Cheltenham?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 144 in the Cheltenham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cheltenham.
