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Top Holiday Rentals in Chester

Our top choices for Chester holiday rentals

Lots of charm and only blocks away from the Root River and Bike trails

9.8 out of 10, Exceptional, (27)
"Had a great time here with my family of 5, including twin toddlers. Plenty of space and even had a children's play room stocked with toys that the kids loved!"
Lots of charm and only blocks away from the Root River and Bike trails

Cozy house / small town living. Attractions include trout capital of Minnesota

5.4 out of 10, (11)
"We came up for the weekend for our fanily reunion . The house is old & smells like an old house, which isn't a bad thing. The house was clean & tidy. We couldn't find the hot tub,but it was all good. We didn't spend much time at the house, except for sleeping & watching tv in the evening. Thank you for a pleasant stay."
The price is £145
includes taxes & fees
10 Sept - 11 Sept
Cozy house / small town living. Attractions include trout capital of Minnesota

Steps to Root River: Home w/ Large Yard!

3.0 star property
6.0 out of 10, (1)
"Dirty dishes, dirty pots and pans, dirty utensils, dusty and unswept floors"
Steps to Root River: Home w/ Large Yard!

Root River Retreat

9.6 out of 10, Exceptional, (38)
"Clean, comfortable (great mattresses/pillows), safe, 2 bedroom, garage. Close to Root River beautiful paved bicycle/hiking trail and good restaurants/shops. "
Root River Retreat

Sage Street Retreat, a quiet and relaxing getaway

10.0 out of 10, Exceptional, (6)
"We really were happy with everything about our stay. Very clean & good beds & quiet neighborhood. Would definitely book again."
The price is £131
includes taxes & fees
1 Sept - 2 Sept
Sage Street Retreat, a quiet and relaxing getaway

Harmony Home w/ Fire Pit: 5 Mi to Niagara Cave!

3.0 star property
Harmony Home w/ Fire Pit: 5 Mi to Niagara Cave!
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

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 £131 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.

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

Lots of charm and only blocks away from the Root River and Bike trails: This holiday home rental outside of Chester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Chester?

While you're exploring the area, Forestville Mystery Cave State Park and Niagara Cave are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Four Daughters Vineyard & Winery and Deer Creek Speedway.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.