Chatham holiday lettings
We found 25 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Chatham to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you expect for your stay, which might include parking and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Chatham
Stylish 4BR South Loop Home State 23-202
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
This is a totally new rehab
Sleeps 10 · 5 bedrooms · 2 bathrooms
6.46.4 out of 10
5 reviews(5 reviews)
Charming house in amazing Chicago with WiFi and AC. Close to many restaurants.
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Charming 4-bedroom house with WiFi, AC in superb Chicago Chatham
Sleeps 10 · 4 bedrooms · 3 bathrooms
House with garage, outdoor dining and basement bar
Sleeps 11 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Sleeps 8 · 4 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
9 reviews(9 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Chatham?
In Chatham, the most common types of holiday rentals are holiday houses and apartments, with several of each available throughout the area. These rentals are typically found in residential neighbourhoods, offering a friendly setting for visitors. Most holiday houses provide spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces such as gardens or patios, great for relaxation after a day of exploring. Apartments, on the other hand, tend to offer a more compact and convenient option, often including modern amenities and comfortable furnishings.
Are there any beach house rentals in Chatham?
In Chatham, Illinois, there are several beach house rentals available, although the area is not renowned for its beachside properties. The holiday rentals typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces that may include patios or decks for relaxation. While Chatham itself is more of a suburban community, those looking for a beach vibe can enjoy these rentals as a comfortable base to explore nearby lakes or rivers.
How much does it cost to rent a holiday home in Chatham?
Prices for holiday rentals in Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chatham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chatham holiday house rentals?
You can find great discounts on house rentals in Chatham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Chatham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chatham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Chatham?
A long-stay holiday rental in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Chatham for a holiday rental?
The best time to visit Chatham for a holiday rental is during the peak season from May to July, with July being the most popular month. This vibrant period draws families and travellers keen to enjoy the warm weather and engage in local festivals and events. Expect pleasant temperatures, often reaching the low 30s Celsius, superb for outdoor activities like hiking and picnicking in the scenic parks nearby.
During these summer months, you'll find a lively atmosphere as locals and visitors alike embrace the outdoors. The community comes alive with various events, allowing you to immerse yourself in Chatham's culture while enjoying the beauty of nature that surrounds you.
If you're looking for a more budget-friendly option, consider planning your visit in December. While this month falls outside the high season, it offers a unique charm with festive decorations and a quieter pace, providing a wonderful opportunity to explore local shops and enjoy the holiday spirit.
Are there any remote work holiday rentals in Chatham?
In Chatham, Illinois, there are several holiday rentals that cater to remote workers. These properties typically offer essential amenities such as Wi-Fi and dedicated office spaces, ensuring a comfortable environment for working while away from home. Many rentals also feature spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Chatham holiday rental?
Book your Chatham holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Chatham home rental booking on Vrbo?
To find Chatham holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chatham holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.