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Our top choices for Chester holiday rentals

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
2.0 star property
French Village
9.8 out of 10, Exceptional, (49 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is £78
includes taxes & fees
17 Feb - 18 Feb
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (3 reviews)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
United States
Norma
Tiny Houses of French Village

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.2 out of 10, Wonderful, (17 reviews)
"Great place to stay! "
United States
Eric
Urban Lofts

Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (1 review)
"Kimberly went out of her way to get a pastry and balloon for my husband’s birthday! Place was extremely clean! They provided everything even down to the Tyl in the bathroom "
United States
Jennifer G.
The price is £120
includes taxes & fees
20 Feb - 21 Feb
Retreat Air - King Bed, Hot Tub & No cleaning fee

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is £71
includes taxes & fees
15 Feb - 16 Feb
Countryside Private Guest Room

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (43 reviews)
"We had a very pleasant stay"
United States
Kate
The price is £135
includes taxes & fees
28 Feb - 1 Mar
Sweet Farm Stay

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is £197
includes taxes & fees
16 Feb - 17 Feb
Homestead Hideaway + Hot Tub

Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay. Kitchen not real well stocked and no WiFi but perfect for what we needed. "
United States
Brandon H.
The price is £152
includes taxes & fees
14 Feb - 15 Feb
Fit and Fueled Studio

Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl

Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl
Waterloo
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful stay! Loved your place!!!"
United States
Sandy G.
Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (48 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is £171
includes taxes & fees
16 Feb - 17 Feb
Peaceful Country Home

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant
Perryville
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!"
United States
Thor L.
The price is £236
includes taxes & fees
15 Feb - 16 Feb
Urban Loft #1 RED · Urban Loft Downtown above BrewCo & Restaurant

Private Home, quiet neighborhood, So. IL, close to St. Louis

Private Home, quiet neighborhood, So. IL, close to St. Louis
Red Bud
10.0 out of 10, Exceptional, (23 reviews)
"Such a great place to stay. This house is so clean, well furnished, and beautiful."
United States
zach a.
The price is £239
includes taxes & fees
28 Feb - 1 Mar
Private Home, quiet neighborhood, So. IL, close to St. Louis

NEW! Speakeasy Cottage

NEW! Speakeasy Cottage
Waterloo
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Spacious, decor wonderful,Convenient to restaurants and coffee cafes The owner was easy to communicate with and hands on We were snowed in and she helped us in every way Look forward to a return visit "
United States
Thomas L.
The price is £254
includes taxes & fees
17 Feb - 18 Feb
NEW! Speakeasy Cottage

New Charming 2-bedroom cottage with Patio in Downtown Waterloo

New Charming 2-bedroom cottage with Patio in Downtown Waterloo
Waterloo
The price is £260
includes taxes & fees
2 Mar - 3 Mar
New Charming 2-bedroom cottage with Patio in Downtown Waterloo

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
Waterloo
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is £185
includes taxes & fees
15 Feb - 16 Feb
In the Country a Beautiful 2-bedroom house with its own private lake

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (3 reviews)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is £174
includes taxes & fees
24 Feb - 25 Feb
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (72 reviews)
"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 £175
includes taxes & fees
28 Feb - 1 Mar
Peter Ray House

Farmstead home w/hot tub

Farmstead home w/hot tub
Marissa
10.0 out of 10, Exceptional, (15 reviews)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is £200
includes taxes & fees
15 Feb - 16 Feb
Farmstead home w/hot tub

Gorgeous, downtown house!

Gorgeous, downtown house!
Perryville
10.0 out of 10, Exceptional, (1 review)
"Our stay was excellent and our host Carisa was a Great person to work with. The house was beautiful. The house worked out great for us. We had 6 people staying and we all had very comfortable beds and our own bathrooms. Great for a large family. "
United States
Doyle or Cheryl D.
The price is £638
includes taxes & fees
16 Feb - 17 Feb
Gorgeous, downtown house!

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.
Ste. Genevieve
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
United States
geri b.
The price is £268
includes taxes & fees
15 Feb - 16 Feb
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
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

Find out more about Chester

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 £78 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 close to the most popular sights in Chester, 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?

"Little Brick House on Main (1865)”: This holiday home rental outside of Chester offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Chester?

Elzie C. Segar Memorial Park and Mississippi River 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 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.