Holiday Rentals in Chester

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Holiday Rentals in Chester

"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (26)
"We took an impromptu overnight from St. Louis. Wonderful place in a nice area. Lots of places to see."
The price is €165
per night
6 May - 7 May
"Little Brick House on Main (1865)”
Peter Ray House
10.0 out of 10, Exceptional, (45)
"Wonderful weekend! We were there to watch a college golf conference tournament. There were four adults and we didn't want to pay the price of two hotel rooms. Booking this VRBO home was just the solution. Everything about it was perfect. 5 star stay for sure. We will be back if given the opportunity."
The price is €226
per night
5 May - 6 May
Peter Ray House
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
10.0 out of 10, Exceptional, (93)
"Gorgeous, clean home in perfect location! Very nice touches though out. The pastries on arrival were delicious! Trolley for wineries picked us up right in front of the house. Walked to restaurants and shops. Beautiful home and beautiful neighborhood. Thank you would love to stay again!"
The 1801 House: A beautiful historic home in the Ste Genevieve Historic District
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Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
10.0 out of 10, Exceptional, (97)
"This site is exactly as advertised. It is a rustic cabin in the middle of town. It is cozy and comfortable and close to everything you need. I has everything you need for a short stay."
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Private Home, quiet neighborhood, So. IL, close to St. Louis
10.0 out of 10, Exceptional, (13)
"Our family (4 adults) stayed at this lovely home for 3 nights for the Eclipse events April 2024. It was a perfect spot with 2 bedrooms and 2 baths on the main floor. It was exceptionally clean and decorated so tastefully. We were even welcomed with homemade chocolate chip cookies and cinnamon rolls. Thanks Missy, for the great accomadations!"
The price is €312
per night
10 May - 11 May
Private Home, quiet neighborhood, So. IL, close to St. Louis
😇Slice of Heaven by Property Lovers 💕
10.0 out of 10, Exceptional, (11)
"Slice of Heaven is a quant little apartment perfect for me and my husband! Very clean with everything you need!"
😇Slice of Heaven by Property Lovers 💕
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
10.0 out of 10, Exceptional, (146)
"Really enjoy it!!"
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (62)
"We held our family Christmas here. 13 people, 7 adults and 6 children. We spent 6 days here. People played pool, ping pong, games, swam and we grilled outside. This house has everything you would in your own home! One day I hosted our huge family gathering of 40+people, plenty of room, it was nice outside and inside and once again everything is provided at the house. I would recommend this house to everyone. Beautiful home. I will rent this house again. Julie"
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Country Home for the Family
10.0 out of 10, Exceptional, (24)
"We were very happy with our stay at the farm house. One problem we did have was several of our group are elderly and climbing the stairs was too much for them. Except for the master bedroom, all the other bedrooms were upstairs. Needless to say, some people that we thought we would have beds for ended up sleeping on the couch downstairs."
Country Home for the Family
June Bug's Loft
10.0 out of 10, Exceptional, (6)
"It was nice to b in the center of town , close to all my doings, I felt very safe and secure"
The price is €114
per night
5 May - 6 May
June Bug's Loft
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
10.0 out of 10, Exceptional, (115)
"We had an excellent experience at the Bauman’s Hillside Hideaway. It was spacious enough to accommodate our large family. The fireplace and fire pit were great additions to add to our visit. The game room had something for everyone."
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Peaceful Country Home
10.0 out of 10, Exceptional, (38)
"This was our second stay and it was a very nice getaway! Our host was great as always!"
The price is €247
per night
7 May - 8 May
Peaceful Country Home
Cozy Haven Guest Cottage Pet Friendly
10.0 out of 10, Exceptional, (22)
"We came in to see family that lives in town. Perfect for us. They live close but, I did not know it when I booked. Would definitely book again!"
Cozy Haven Guest Cottage Pet Friendly
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
10.0 out of 10, Exceptional, (50)
"This was a perfect cabin for our family weekend. The cabin is clean and comfortable. There are many small, charming details. The doors and stairs add to the rustic feel of the home. The owner and his adorable helpers were there to greet us, but then gave us privacy. I am sure this will not be our last visit, as everyone loved the cabin. I highly recommend it for anybody staying in this area."
The price is €431
per night
5 May - 6 May
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Hidden Gem, scenic views off private balconies, incredible food and wine
10.0 out of 10, Exceptional, (17)
"The Weingarten Vineyard and Inn is a diamond in the rough and so amazing. We own our own business and needed a weekend getaway to strategize together. We still aren't sure how we found this place but it was exactly what we needed! The stars at night were breathtaking, and the quiet peaceful vineyard was a much needed reprieve. The Inn is gorgeous and was expertly built by the owners. We were well taken care of - a bottle of Brut welcomed us in our room. We will definitely have this as our #1...
Hidden Gem, scenic views off private balconies, incredible food and wine
Wren’s Hideaway 3 Bedrooms 2 Full baths Charming & Relaxing
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay, the house was perfect. Lots of space and close to all the historic places. We learned a lot about the town up close and everyone in town was so friendly."
Wren’s Hideaway 3 Bedrooms 2 Full baths Charming & Relaxing
Countryside Private Guest Room
10.0 out of 10, Exceptional, (6)
"Perfect little place to stay when you are on the move! Quiet, clean and suited our needs perfectly. Little fridge, little microwave and one cup coffee maker for convenience since we were on the go and taking our meals out. Clean and comfy and hostess and host were friendly and brought local sweet treats to enjoy. Definitely would stay with them again...suited our needs perfectly! Beautiful country setting and very relaxing!"
The price is €93
per night
4 May - 5 May
Countryside Private Guest Room
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
10.0 out of 10, Exceptional, (7)
"It was very peaceful and relaxing. Close to town."
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Tiny Houses of French Village
2.5 star property
10.0 out of 10, Exceptional, (1)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
The price is €238
per night
5 May - 6 May
Tiny Houses of French Village
Sweet Farm Stay
10.0 out of 10, Exceptional, (15)
"We booked this a year and four months before the eclipse, so we could get to totality. This property was beautiful, quiet, and isolated, which is just what we needed! Being able to sit outside and just listen to nature was wonderful. We lucked out with the weather - summerlike and beautiful as well. Jill messaged us with all the information we needed and gave us choices when someone would be there for some maintenance. Very happy with this place."
The price is €164
per night
4 May - 5 May
Sweet Farm Stay
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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.

Other types of properties in Chester you may be interested in

Holiday Inn Express & Suites Perryville, an IHG Hotel
2.5 star property
9.4 out of 10, Exceptional, (383)
"Very clean. Large bathroom. "
The price is €109
per night
6 May - 7 May
Holiday Inn Express & Suites Perryville, an IHG Hotel
Best Western Chester Hotel
2.5 star property
8.6 out of 10, Excellent, (246)
"It was a convenient stay, staff were nice. Breakfast was simple. There’s A Walmart, Gas Station, and other fat food places close by. "
The price is €90
per night
8 May - 9 May
Best Western Chester Hotel
Super 8 by Wyndham Perryville
2.0 star property
8.6 out of 10, Excellent, (732)
"We were in rm 101 right next to the stairs. They are carpeted but people drag their suitcases down them and at 6am, pretty annoying. "
The price is €67
per night
27 May - 28 May
Super 8 by Wyndham Perryville
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.

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as €93 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Chester Skating Rink, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chester has to offer?

The 1801 House: A beautiful historic home in the Ste Genevieve Historic District: This holiday home rental outside of Chester is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chester Skating Rink. Other places in town to visit include Fort Kaskaskia and Popeye Museum.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.

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