Estia Villas - Vacation Rentals in Chester
Apartment
10.0
(
287 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
630 ft²
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $193
/Night
7 Nights - $1,351
House
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
613.54 ft²
-
Parking
-
Balcony/Terrace
-
Internet -
Security/Safety
US $138
/Night
7 Nights - $966
Bed & Breakfast
10.0
(
21 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Balcony/Terrace
-
Air Conditioner
US $173
/Night
7 Nights - $1,214
House
10.0
(
188 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $207
/Night
7 Nights - $1,446
Apartment
9.6
(
182 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $138
/Night
7 Nights - $969
House
10.0
(
111 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1550 ft²
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $212
/Night
7 Nights - $1,482
House
10.0
(
85 Reviews
)
5 Bedrooms
4 Bathrooms
23 Guests
4500 ft²
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $1,459
/Night
7 Nights - $10,210
House
10.0
(
72 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $181
/Night
7 Nights - $1,270
See More Chester Vacation Rentals
Luxury Places to Stay in Chester
Over 99+
Luxury Places to Stay in or Near Chester
House
10.0
(
10 Reviews
)
7 Bedrooms
4 Bathrooms
18 Guests
6800 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,997
/Night
7 Nights - $13,976
House
10.0
(
1 Review
)
7 Bedrooms
4 Bathrooms
18 Guests
6802.79 ft²
-
Private Pool
-
Private Beach -
Parking
-
Pool
US $1,413
/Night
7 Nights - $9,891
Apartment
10.0
(
1 Review
)
5 Bedrooms
3 Bathrooms
10 Guests
3498 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $875
/Night
7 Nights - $6,127
US $870
/Night
7 Nights - $6,092
Cabin
10.0
(
5 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $529
/Night
7 Nights - $3,706
Cabin
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Hot Tub
-
Kitchen
-
Air Conditioner
-
Laundry
US $529
/Night
7 Nights - $3,706
House
9.8
(
8 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $448
/Night
7 Nights - $3,133
Apartment
1 Bedroom
2 Bathrooms
4 Guests
861 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $370
/Night
7 Nights - $2,593
See More Chester Luxury Vacation Rentals
Find More Chester Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chester
Over 14+
Top-Rated Vacation Rentals with a Pool in or Near Chester
Other
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Balcony/Terrace
-
Internet
US $84
/Night
7 Nights - $591
Hotel
9.2
(
600 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $126
/Night
7 Nights - $881
Hotel
9.2
(
411 Reviews
)
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $135
/Night
7 Nights - $948
US $82
/Night
7 Nights - $577
US $61
/Night
7 Nights - $424
US $88
/Night
7 Nights - $614
US $77
/Night
7 Nights - $541
US $87
/Night
7 Nights - $609
See More Chester Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Chester
Over 18+
Pet-Friendly Vacation Rentals in or Near Chester
House
10.0
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $281
/Night
7 Nights - $1,968
House
9.5
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1797.57 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Internet
US $268
/Night
7 Nights - $1,876
Apartment
9.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $167
/Night
7 Nights - $1,172
Apartment
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $317
/Night
7 Nights - $2,218
Cabin
9.6
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $240
/Night
7 Nights - $1,682
House
9.0
(
8 Reviews
)
2 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $253
/Night
7 Nights - $1,769
House
9.6
(
22 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
800 ft²
-
Hot Tub
-
Parking
-
Spa -
Balcony/Terrace
US $78
/Night
7 Nights - $549
Apartment
5.0
(
1 Review
)
1 Bedroom
1 Bathroom
6 Guests
2000 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $145
/Night
7 Nights - $1,015
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io
Large Vacation Homes & Villas in Chester
Over 3+
Large Vacation Homes & Villas in or Near Chester
House
9.8
(
7 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
1980 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $596
/Night
7 Nights - $4,173
Cabin
10.0
(
16 Reviews
)
6 Bedrooms
5 Bathrooms
12 Guests
3700 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,169
/Night
7 Nights - $8,186
Other
4.9
(
15 Reviews
)
7 Bedrooms
4 Bathrooms
16 Guests
6000 ft²
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
US $1,000
/Night
7 Nights - $7,000
See More Family Vacation Rentals in Chester on FVR
Wheelchair Accessible Vacation Homes in Chester
Over 4+
Wheelchair Accessible Vacation Homes in or Near Chester
Hotel
8.4
(
105 Reviews
)
247.57 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $77
/Night
7 Nights - $536
Hotel
8.8
(
664 Reviews
)
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $95
/Night
7 Nights - $667
Hotel
5.7
(
62 Reviews
)
322.92 ft²
-
Hot Tub
-
Parking
-
Pool
-
Air Conditioner
US $80
/Night
7 Nights - $560
US $96
/Night
7 Nights - $671
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Over 49+
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
10.0
(
39 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $192
/Night
7 Nights - $1,343
House
9.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
785.77 ft²
-
Parking
-
Internet
-
Child Friendly -
Sports/Activities
US $174
/Night
7 Nights - $1,216
US $67
/Night
7 Nights - $466
House
10.0
(
9 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
610 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $144
/Night
7 Nights - $1,005
House
10.0
(
8 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Air Conditioner
-
Internet
-
Laundry
-
Bedding/Linens
US $188
/Night
7 Nights - $1,317
Cottage
10.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $185
/Night
7 Nights - $1,298
House
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $98
/Night
7 Nights - $689
House
9.8
(
115 Reviews
)
3 Bedrooms
1 Bathroom
9 Guests
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $191
/Night
7 Nights - $1,340
See More Chester Vacation Rental Deals
Instantly Bookable Vacation Homes in Chester
Over 19+
Instantly Bookable Vacation Homes in or Near Chester
Cottage
10.0
(
43 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
784 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $218
/Night
7 Nights - $1,526
House
9.8
(
63 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $209
/Night
7 Nights - $1,460
Apartment
1 Bedroom
1 Bathroom
4 Guests
538 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $319
/Night
7 Nights - $2,232
New
Apartment
1 Bedroom
1 Bathroom
4 Guests
861 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $310
/Night
7 Nights - $2,169
House
10.0
(
77 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $119
/Night
7 Nights - $835
House
10.0
(
31 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $239
/Night
7 Nights - $1,670
US $118
/Night
7 Nights - $823
Apartment
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $140
/Night
7 Nights - $980
See More Chester Short-Term Vacation Rentals
About Chester Vacation Rentals
With more than 108 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester. Places to stay near Chester are 690 ft² on average, with prices averaging US $257 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chester
| Type | Count |
|---|---|
| Vacation Homes | 38 |
| Holiday Apartments | 29 |
| Hotels | 25 |
| Cabin Rentals | 5 |
| Cottages | 5 |
| Others | 3 |
| B&B | 2 |
Use these Quick Filters to Find a Vacation Rental in Chester
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.
Weather in Chester
View the weather forecast for Chester before booking your Chester 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
Top Attractions Around Chester, IL
Estiavillas offers a large selection of top attractions around Chester. Research things to do on your vacation before you visit Chester.
Elzie C. Segar Memorial Park
Chester Skating Rink
Sparta Country Club
Popeye Museum
Fort Kaskaskia
Kaskaskia Bell
Misselhorn Art Gallery
Mary's River Covered Bridge
Memorial Hospital
Shawnee National Forest
Mark Twain National Forest
National Shrine of Our Lady of the Miraculous Medal
Crown Valley Winery
Washington County Courthouse
Pierre Menard Home
Lake Murphysboro State Park
Perryville Country Club
Hazel Creek
Other Places to Stay Near Chester, IL
Memorial Hospital
111 Properties
Elzie C. Segar Memorial Park
111 Properties
Popeye Museum
110 Properties
Chester Skating Rink
109 Properties
Kaskaskia Bell
109 Properties
Mary's River Covered Bridge
106 Properties
Saint Mary
103 Properties
Bremen
97 Properties
Prairie du Rocher
91 Properties
Sparta
64 Properties
Misselhorn Art Gallery
62 Properties
Baldwin
52 Properties
Chester Vacation Rental Frequently Asked Questions
Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
How many vacation rentals are available in Chester?
Currently, the total number of properties listed in 2026 is over 108 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.
