Chatham Holiday Rentals
New
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
905 ft²
Parking
Kitchen
Air Conditioner
Internet
US $444/Night
7 Nights - US $3,110
Apartment
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
US $686/Night
7 Nights - US $4,800
House
- Chicago
- ·
- Greater Grand Crossing
- 0.48 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
US $450/Night
7 Nights - US $3,150
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $255/Night
7 Nights - US $1,785
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
16 Guests
3896.54 ft²
View- Air Conditioner
- Internet
Pet Friendly
US $368/Night
7 Nights - US $2,574
House
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $117/Night
7 Nights - US $821
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
935 ft²
Hot Tub- Parking
- Kitchen
- Air Conditioner
US $509/Night
7 Nights - US $3,563
Apartment
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $262/Night
7 Nights - US $1,831
Apartment
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $211/Night
7 Nights - US $1,477
Luxury Holiday Rentals in Chatham
Over 315+ Luxury Holiday Rentals in or Near Chatham
New
House
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,184/Night
7 Nights - US $15,288
Other
10.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,299/Night
7 Nights - US $9,092
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.77 mi to center
5.0Average
(4 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Kitchen
- Air Conditioner
- Internet
Bedding/Linens
US $854/Night
7 Nights - US $5,981
New
House
- Chicago
- ·
- Auburn Gresham
- 1.34 mi to center
9.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $808/Night
7 Nights - US $5,653
Apartment
9.8Exceptional
(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
1850 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $719/Night
7 Nights - US $5,036
New
House
9.8Exceptional
(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $708/Night
7 Nights - US $4,955
House
9.2Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
12 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $689/Night
7 Nights - US $4,820
House
- Chicago
- ·
- Greater Grand Crossing
- 0.42 mi to center
6 Bedrooms
2 Baths
9 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $670/Night
7 Nights - US $4,690
Condo
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $643/Night
7 Nights - US $4,500
Top-Rated Holiday Rentals with a Pool in Chatham
Over 1+ The Best Private Villas and Holiday Rentals in Chatham with a Pool
House
4.8Average
(3 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
US $356/Night
7 Nights - US $2,493
Pet-Friendly Holiday Rentals in Chatham
Over 81+ Pet-Friendly Holiday Rentals in or Near Chatham
Apartment
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $236/Night
7 Nights - US $1,653
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $405/Night
7 Nights - US $2,835
New
Condo
2 Bedrooms
2 Baths
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $139/Night
7 Nights - US $971
Apartment
9.2Exceptional
(22 Reviews)
5 Bedrooms
2 Baths
10 Guests
1700.7 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $464/Night
7 Nights - US $3,248
Apartment
2 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $112/Night
7 Nights - US $786
New
Apartment
- Chicago
- ·
- South Chicago
- 0.35 mi to center
2 Bedrooms
1 Bath
4 Guests
1613 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $85/Night
7 Nights - US $598
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $422/Night
7 Nights - US $2,952
New
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $271/Night
7 Nights - US $1,895
Apartment
- Chicago
- ·
- East Beverly
- 0.52 mi to center
9.8Exceptional
(6 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $240/Night
7 Nights - US $1,681
Large Holiday Rentals and Private Villas in Chatham
Over 43+ Large Holiday Rentals and Private Villas in or Near Chatham
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $564/Night
7 Nights - US $3,947
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.52 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
9 Guests
2098.96 ft²
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,639
House
- Chicago
- ·
- South Shore
- 0.30 mi to center
9.4Exceptional
(34 Reviews)
3 Bedrooms
3 Baths
12 Guests
2200 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $554/Night
7 Nights - US $3,879
House
- Chicago
- ·
- Greater Grand Crossing
- 0.29 mi to center
9.7Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
12 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $629/Night
7 Nights - US $4,404
House
- Chicago
- ·
- Avalon Park
- 0.2 mi to center
8.4Excellent
(14 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $519/Night
7 Nights - US $3,632
House
- Chicago
- ·
- Avalon Park
- 0.10 mi to center
6.0Good
(1 Review)
6 Bedrooms
2 Baths
6 Guests
2600 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $172/Night
7 Nights - US $1,207
New
House
5 Bedrooms
2 Baths
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $537/Night
7 Nights - US $3,757
Apartment
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Air Conditioner
- Internet
- Laundry
US $487/Night
7 Nights - US $3,412
House
- Chicago
- ·
- South Shore
- 0.94 mi to center
4 Bedrooms
2 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $427/Night
7 Nights - US $2,989
Wheelchair Accessible Holiday Homes in Chatham
Over 8+ Wheelchair Accessible Holiday Homes in or Near Chatham
Apartment
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $597/Night
7 Nights - US $4,182
Apartment
8.9Fabulous
(15 Reviews)
3 Bedrooms
1 Bath
6 Guests
1162.5 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $126/Night
7 Nights - US $882
Hotel
- Chicago
- ·
- Washington Heights
- 0.51 mi to center
7.0Very Good
(468 Reviews)
1 Bath
- Parking
- Kitchen
- Internet
- Child Friendly
US $117/Night
7 Nights - US $822
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.81 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
650 ft²
- Kitchen
- Internet
- Child Friendly
Wheelchair Accessible
US $520/Night
7 Nights - US $3,642
House
7.5Very Good
(35 Reviews)
1 Bedroom
1 Bath
2 Guests
139.93 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $73/Night
7 Nights - US $510
Hotel
- Chicago
- ·
- Washington Heights
- 0.51 mi to center
5.6Average
(63 Reviews)
1 Bath
204.51 ft²
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
Accessibility
US $76/Night
7 Nights - US $534
Hotel
- Chicago
- ·
- Greater Grand Crossing
- 0.88 mi to center
2.1Average
(46 Reviews)
5 Baths
150.69 ft²
- Parking
- Pet Friendly
- Child Friendly
- Wheelchair Accessible
US $107/Night
7 Nights - US $752
Hotel
- Chicago
- ·
- Greater Grand Crossing
- 0.75 mi to center
1.9Average
(9 Reviews)
2 Baths
150.69 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $65/Night
7 Nights - US $452
Chatham Private Villas and Holiday Homes Under $200
Over 125+ Chatham Private Villas and Holiday Homes Under $200
House
- Chicago
- ·
- South Shore
- 0.46 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,305
House
- Chicago
- ·
- South Shore
- 0.34 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5381.95 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $75/Night
7 Nights - US $525
Hotel
4.0Average
(75 Reviews)
1 Bath
- Parking
- Air Conditioner
- Child Friendly
Toiletries
US $110/Night
7 Nights - US $772
House
- Chicago
- ·
- South Chicago
- 1.08 mi to center
1 Bedroom
1 Bath
3 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $180/Night
7 Nights - US $1,262
House
9.3Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
1076.39 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $86/Night
7 Nights - US $599
New
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.58 mi to center
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $179/Night
7 Nights - US $1,254
New
House
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Air Conditioner
- Internet
- Laundry
US $170/Night
7 Nights - US $1,192
Condo
- Chicago
- ·
- Jackson Park Highlands
- 0.07 mi to center
1 Bedroom
2 Baths
1 Guest
- Hot Tub
- Air Conditioner
- Laundry
Designated Smoking Area
US $166/Night
7 Nights - US $1,163
House
2 Bedrooms
2 Baths
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Bedding/Linens
US $156/Night
7 Nights - US $1,089
Instantly Bookable Holiday Homes in Chatham
Over 137+ Instantly Bookable Holiday Homes in or Near Chatham
Apartment
9.4Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $249/Night
7 Nights - US $1,742
Condo
8.6Fabulous
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Kitchen
- Internet
US $298/Night
7 Nights - US $2,087
House
8.0Excellent
(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,841
Condo
- Chicago
- ·
- South Shore
- 0.90 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $406/Night
7 Nights - US $2,839
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $218/Night
7 Nights - US $1,525
Apartment
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $138/Night
7 Nights - US $968
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 1.06 mi to center
2 Bedrooms
1 Bath
3 Guests
900 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $136/Night
7 Nights - US $951
Apartment
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $112/Night
7 Nights - US $785
Apartment
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $101/Night
7 Nights - US $704
Book a Last Minute Place to Stay in Chatham
About Casai's Private Villas and Holiday Rentals in Chatham
Discover more than 324 vacation rentals available in Chatham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chatham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chatham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chatham. On average, places to stay near Chatham offer 649.03 ft², with nightly prices averaging US $306.
With Casai, finding and comparing holiday rentals in Chatham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Chatham
| Type | Count |
|---|---|
| Holiday Apartments | 159 |
| Vacation Homes | 126 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Chatham
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chatham.
Weather in Chatham, IL
View the weather forecast for Chatham before booking your Chatham Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Chatham, IL
Frequently Asked Questions About Chatham?
What are the top holiday rentals in Chatham?
With numerous options available in Chatham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chatham:
- University of Chicago Condo - 2 Baths, Private Parking & Private Entry
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
- A 3-bedroom, 2-bathroom residence that provides ample space and comfort.
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- The Brown House - A luxurious UChicago Campus stay
- Stylish 2BR Near Hyde Park, UChicago & Lake
- Maison Blanc Noir - Victorian Estate with Two King Beds
- Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
- Cozy & Near Downtown, Hyde Park & the Metra
- Private Basement Suite-Completely separate from the rest of the house
Which holiday homes in Chatham are best for families?
If you're searching for a family-friendly holiday home in Chatham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chatham:
- Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras
- Parisian Retreat 6min to Main Quandrangle U of C
- Best Motel By OYO Chicago I-90
How many Casai.com holiday rentals are available in Chatham?
As of 2026, Casai boasts over 324 properties listed in the Chatham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chatham.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Greater Grand Crossing Vacation Rentals in Chicago, Illinois | 622 |
| Princeton Park Vacation Rentals in Chicago, Illinois | 144 |
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