Chatham Vacation Rentals & Ski-in/Ski-out Homes
New
House
4 Bedrooms
3 Baths
12 Guests
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $672/Night
7 Nights - US $4,705
Apartment
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
US $834/Night
7 Nights - US $5,840
Hotel
- Chicago
- ·
- Washington Heights
- 0.51 mi to center
7.4Very Good
(335 Reviews)
1 Bath
- Kitchen
- Parking
- Internet
- Child Friendly
US $129/Night
7 Nights - US $904
Apartment
4 Bedrooms
2 Baths
10 Guests
US $370/Night
7 Nights - US $2,591
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Hot Tub
Pet Friendly- Parking
- Air Conditioner
US $405/Night
7 Nights - US $2,835
House
- Chicago
- ·
- Auburn Gresham
- 1.31 mi to center
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $314/Night
7 Nights - US $2,197
Condo
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $381/Night
7 Nights - US $2,669
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
US $230/Night
7 Nights - US $1,607
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $224/Night
7 Nights - US $1,569
Luxury Places to Stay in Chatham
Over 291+ Luxury Places to Stay in or Near Chatham
Other
10.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,196/Night
7 Nights - US $8,370
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,144/Night
7 Nights - US $8,010
Apartment
9.7Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,038/Night
7 Nights - US $7,266
Condo
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,011/Night
7 Nights - US $7,075
Condo
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $863/Night
7 Nights - US $6,038
House
- Chicago
- ·
- Auburn Gresham
- 1.34 mi to center
9.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $680/Night
7 Nights - US $4,757
House
- Chicago
- ·
- Greater Grand Crossing
- 0.42 mi to center
6 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $672/Night
7 Nights - US $4,704
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
Apartment
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $589/Night
7 Nights - US $4,124
Top-Rated Vacation Rentals with a Pool in Chatham
Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Chatham
House
4.8Average
(3 Reviews)
5 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
US $356/Night
7 Nights - US $2,493
Pet-Friendly Vacation Rentals in Chatham
Over 74+ Pet-Friendly Vacation Rentals in or Near Chatham
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $271/Night
7 Nights - US $1,900
Apartment
9.2Exceptional
(22 Reviews)
5 Bedrooms
2 Baths
10 Guests
1700.7 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $464/Night
7 Nights - US $3,248
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $329/Night
7 Nights - US $2,300
Apartment
9.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
796.53 ft²
View- Pet Friendly
- Parking
- Air Conditioner
US $183/Night
7 Nights - US $1,281
Apartment
- Chicago
- ·
- South Shore
- 0.48 mi to center
8.4Excellent
(17 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $128/Night
7 Nights - US $898
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $215/Night
7 Nights - US $1,507
New
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.80 mi to center
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $183/Night
7 Nights - US $1,281
Apartment
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $105/Night
7 Nights - US $735
Apartment
- Chicago
- ·
- South Chicago
- 0.35 mi to center
2 Bedrooms
1 Bath
4 Guests
1613 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $87/Night
7 Nights - US $610
Large Vacation Homes & Villas in Chatham
Over 39+ Large Vacation Homes & Villas in or Near Chatham
House
- Chicago
- ·
- South Shore
- 0.30 mi to center
9.6Exceptional
(28 Reviews)
3 Bedrooms
3 Baths
12 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $451/Night
7 Nights - US $3,160
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.52 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
9 Guests
2098.96 ft²
- Balcony/Terrace
Breakfast- Kitchen
- Parking
US $377/Night
7 Nights - US $2,639
Apartment
9.6Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
1850 ft²
- Kitchen
- Parking
- Air Conditioner
- Internet
US $559/Night
7 Nights - US $3,915
House
8.9Fabulous
(6 Reviews)
3 Bedrooms
3 Baths
12 Guests
215.28 ft²
- View
- Parking
- Air Conditioner
- Internet
US $331/Night
7 Nights - US $2,318
House
9.2Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
12 Guests
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $580/Night
7 Nights - US $4,060
House
9.0Exceptional
(11 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $561/Night
7 Nights - US $3,930
House
- Chicago
- ·
- Avalon Park
- 0.13 mi to center
7.4Very Good
(3 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $475/Night
7 Nights - US $3,325
House
- Chicago
- ·
- Avalon Park
- 0.10 mi to center
6.0Good
(1 Review)
6 Bedrooms
2 Baths
6 Guests
2600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $177/Night
7 Nights - US $1,236
House
5.8Average
(6 Reviews)
5 Bedrooms
2 Baths
10 Guests
1400 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $414/Night
7 Nights - US $2,899
Wheelchair Accessible Vacation Homes in Chatham
Over 6+ Wheelchair Accessible Vacation Homes in or Near Chatham
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.81 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
650 ft²
- Fireplace/Heating
- Kitchen
- Internet
- Child Friendly
US $520/Night
7 Nights - US $3,642
Apartment
8.9Fabulous
(15 Reviews)
3 Bedrooms
1 Bath
6 Guests
1162.5 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $126/Night
7 Nights - US $882
House
7.5Very Good
(35 Reviews)
1 Bedroom
1 Bath
2 Guests
139.93 ft²
- Fireplace/Heating
- 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
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
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
- Pet Friendly
- Parking
- Child Friendly
Wheelchair Accessible
US $70/Night
7 Nights - US $488
Hotel
- Chicago
- ·
- Greater Grand Crossing
- 0.75 mi to center
1.9Average
(9 Reviews)
2 Baths
150.69 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $65/Night
7 Nights - US $452
Chatham Resorts and Airbnb Homes Under $200
Over 127+ Chatham Resorts and Airbnb Homes Under $200
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $188/Night
7 Nights - US $1,317
House
- Chicago
- ·
- South Shore
- 0.34 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5381.95 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $75/Night
7 Nights - US $525
Hotel
4.2Average
(60 Reviews)
1 Bath
- Parking
- Air Conditioner
- Child Friendly
Toiletries
US $89/Night
7 Nights - US $624
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $123/Night
7 Nights - US $864
House
9.3Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
1076.39 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $76/Night
7 Nights - US $532
House
7.0Very Good
(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $184/Night
7 Nights - US $1,288
House
- Chicago
- ·
- South Shore
- 0.46 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $171/Night
7 Nights - US $1,198
Condo
- Chicago
- ·
- Jackson Park Highlands
- 0.07 mi to center
1 Bedroom
2 Baths
1 Guest
- Hot Tub
- Fireplace/Heating
- Air Conditioner
Laundry
US $166/Night
7 Nights - US $1,163
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $142/Night
7 Nights - US $994
Instantly Bookable Vacation Homes in Chatham
Over 123+ Instantly Bookable Vacation Homes in or Near Chatham
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
7 Guests
1117 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $245/Night
7 Nights - US $1,718
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
935 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $413/Night
7 Nights - US $2,894
Condo
8.8Fabulous
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Kitchen
- Parking
- Internet
US $235/Night
7 Nights - US $1,648
Condo
- Chicago
- ·
- South Shore
- 0.90 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $276/Night
7 Nights - US $1,933
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $134/Night
7 Nights - US $935
Apartment
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $91/Night
7 Nights - US $637
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $84/Night
7 Nights - US $591
Hotel
10.0Exceptional
(7 Reviews)
2 Baths
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $241/Night
7 Nights - US $1,684
Apartment
- Chicago
- ·
- East Beverly
- 0.52 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $207/Night
7 Nights - US $1,449
Book a Last Minute Place to Stay in Chatham
About Chatham Vacation Rentals
Explore over 300 vacation rentals in Chatham with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Chatham for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Chatham. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Chatham tailored to your preferences. On average, these rentals offer 653.55 ft² of space, and are priced at an average of US $293 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Chatham at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Chatham
| Type | Count |
|---|---|
| Holiday Apartments | 146 |
| Vacation Homes | 115 |
| Cottages | 1 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Chatham
★ Pro Tip: Discover Your Ideal Vacation Rental in Chatham with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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 vacation rentals in Chatham?
When organizing your trip to Chatham, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Chatham. Peruse our collection of highly-rated properties and secure your reservation today.
- Modern Apt Near U of Chicago!
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
- University of Chicago Condo-Upgraded and Spacious w/Parking
- The Brown House - A luxurious UChicago Campus stay
- High-end 2Bdrm Garden Apt. Where Comfort Meets Style
- Charming 3-bedroom apartment in superb Chicago with WiFi
- Maison Blanc Noir - Victorian Estate with Two King Beds
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- A 3-bedroom, 2-bathroom residence that provides ample space and comfort.
- Cozy & Near Downtown, Hyde Park & the Metra
Which vacation homes or resorts in Chatham are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Chatham. Enjoy great views, locations and save money with SunSki Resorts.™
- Fully furnished, modern short-term stay home near Obama Presidential Library.
- Chateau de Woodlawn - Room I - La Tour Eiffel
- Best Motel By OYO Chicago I-90
How many SunSkiResorts vacation rentals or resorts are available in Chatham?
Discover the ideal vacation rental in Chatham with SunSki Resorts™. We provide an extensive selection of over 300 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Chatham.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Greater Grand Crossing Vacation Rentals in Chicago, Illinois | 611 |
| Princeton Park Vacation Rentals in Chicago, Illinois | 144 |
People Also Ask
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