Chester Vacation Rentals

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Oct 25 - Oct 26
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in Chester

Exterior
Private Cabin with Pond on Family Farm
Private Cabin with Pond on Family Farm
10.0 out of 10, Exceptional, (91)
"Great weather great view great time was our 2nd stay going back again next fall "
United States
Paul D.
Private Cabin with Pond on Family Farm
Interior
Cozy Haven Little Hidden Gem Sleeps 4
Cozy Haven Little Hidden Gem Sleeps 4
9.8 out of 10, Exceptional, (50)
"Super cute cottage! Very clean. Quick walk to town. We thoroughly enjoyed our stay here. "
United States
Marianne A.
Cozy Haven Little Hidden Gem Sleeps 4
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4
2.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing property super quiet and chill."
United States
Aden
⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4
Outdoor dining
Doves Nest Guest House<br> Tranquil & Relaxing
Doves Nest Guest House<br> Tranquil & Relaxing
9.8 out of 10, Exceptional, (50)
"Outstanding! I highly recommend to everyone! So well decorated with every amenity! Great location and easy walk to restaurants and activities and shopping! Great hosts!"
United States
Shari
The price is ￥15,656
￥30,610 total
includes taxes & fees
Oct 27 - Oct 28
Doves Nest Guest House<br> Tranquil & Relaxing
Exterior detail
"Little Brick House on Main (1865)”
"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (56)
"Great place to stay!"
United States
Lettitia B.
The price is ￥18,128
￥24,232 total
includes taxes & fees
Nov 6 - Nov 7
"Little Brick House on Main (1865)”
Property grounds
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
10.0 out of 10, Exceptional, (172)
"Nice location, clean and inviting."
United States
Laura C.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!
Beautiful Modern Loft In Wine Country!
10.0 out of 10, Exceptional, (268)
"The perfect escape from the city! Gorgeous views of the country while enjoying our morning coffee. "
United States
Melissa L.
The price is ￥22,583
￥27,571 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Modern Loft In Wine Country!
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
10.0 out of 10, Exceptional, (3)
"Tiny house was absolutely perfect for a quick getaway or even a longer stay had everything we needed except a toaster! Owners were great on getting in touch for anything needed."
United States
Deborah J.
The price is ￥30,075
￥39,383 total
includes taxes & fees
Nov 5 - Nov 6
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
1 bedroom, iron/ironing board, free WiFi, bed sheets
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
10.0 out of 10, Exceptional, (123)
"Cozy, clean & comfortable."
United States
Donna K.
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Dining
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
10.0 out of 10, Exceptional, (5)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is ￥27,466
￥42,310 total
includes taxes & fees
Nov 2 - Nov 3
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Terrace/patio
Secluded Lodge with Private Lake Minutes from St. Louis
Secluded Lodge with Private Lake Minutes from St. Louis
10.0 out of 10, Exceptional, (209)
"For a group of empty nesters, a girls trip has a different meaning than it does when you're in your 20s and 30s. This place gives you a chance to relax, let loose a little, get out of your comfort zone a little, fish, go kayaking, and spend some well deserved time together. "
United States
Jamie W.
Secluded Lodge with Private Lake Minutes from St. Louis
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (136)
"It’s perfect and already booking next year!"
United States
Joan H.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Fridge, microwave, oven, stovetop
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
10.0 out of 10, Exceptional, (3)
"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "
United States
Tim M.
The price is ￥22,889
￥45,753 total
includes taxes & fees
Oct 27 - Oct 28
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, (57)
"Wonderful place to stay in Ste Genevieve wine country"
United States
Nicholas S.
The price is ￥45,777
￥60,731 total
includes taxes & fees
Nov 13 - Nov 14
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
55-inch Smart TV with digital channels, TV, streaming services
Urban Lofts
Urban Lofts
3.0 star property
9.2 out of 10, Wonderful, (17)
"Great place to stay! "
United States
Eric
Urban Lofts
Property grounds
Peter Ray House
Peter Ray House
10.0 out of 10, Exceptional, (70)
"The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!"
United States
Deborah
The price is ￥20,636
￥34,343 total
includes taxes & fees
Oct 31 - Nov 1
Peter Ray House
Exterior
In the Country a Beautiful 2-bedroom house with its own private lake
In the Country a Beautiful 2-bedroom house with its own private lake
10.0 out of 10, Exceptional, (2)
"Do yourself a favor and book this property. We have booked many properties all over Illinois and Missouri and this place just jumped to the top of our list. The property is so relaxing in countless ways. Very secluded, yet restaurants and everything you need are just 15 minutes away in Waterloo."
United States
Jeff
The price is ￥24,033
￥38,407 total
includes taxes & fees
Oct 27 - Oct 28
In the Country a Beautiful 2-bedroom house with its own private lake
Outdoor spa tub
Homestead Hideaway + Hot Tub
Homestead Hideaway + Hot Tub
10.0 out of 10, Exceptional, (27)
"The residence was lovely in that it was just “away” from everything. We stayed in, cooked meals, played board games, enjoyed the hot tub and took in some movies. A lovely place to just get away. "
United States
Michael M.
The price is ￥21,363
￥39,297 total
includes taxes & fees
Nov 17 - Nov 18
Homestead Hideaway + Hot Tub
Exterior
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (76)
"Great experience We had a manager meeting and two day retreat Hostess was very accommodating and responsive The property is very private and peaceful The accommodations are top shelf The kitchen and cooking facilities are very well stocked and we truly enjoyed not having to leave for anything !!!We are already planning on our next stay Thank you "
United States
Ted H.
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Exterior
Hot Tub & Creek Views: Secluded Perryville Cabin
Hot Tub & Creek Views: Secluded Perryville Cabin
9.8 out of 10, Exceptional, (6)
"Property was excellent house was really nice and in a great location would stay there again for sure "
United States
David R.
Hot Tub & Creek Views: Secluded Perryville Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

10/10 Excellent
"The room was clean and the staff were friendly. "
RODNEY 1-night trip
Posted 5 days ago
Baymont by Wyndham Chester IL

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near top attractions in Chester, or you can choose a more secluded option if you're looking for relaxation. Chester is known for its golf courses and parks. Make sure you have time to check out the restaurants and entertainment choices during your trip.

What are some of the best vacation home rentals that Chester has to offer?

Doves Nest Guest House
Tranquil & Relaxing : This vacation home rental outside of Chester is located in the city center and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Popeye Museum is one of the cultural attractions. Other places in town to visit include Fort Kaskaskia and Kaskaskia Bell.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can stay in for a short or long stay in Chester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.