Chester Vacation Rentals

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Vacation Rentals in Chester

Our top choices for Chester vacation 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."
$178 nightly
The price is $191
Sep 10 - Sep 11
Total with taxes and fees
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)
"Awesome "
Root River Retreat

Friendly-Farm Retreat

10.0 out of 10, Exceptional, (74)
"We loved our stay. Owners were friendly and helpful. All the animals were great. Would for sure stay here again next time we come to the area."
Friendly-Farm 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."
$165 nightly
The price is $173
Sep 1 - Sep 2
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $173 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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 vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near the most popular local attractions in Chester, or you can choose a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Chester?

Harmony Home w/ Fire Pit: 5 Mi to Niagara Cave!: This vacation home rental outside of Chester offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 larger area, you’ll find Four Daughters Vineyard & Winery and Deer Creek Speedway.

What’s a vacation rental in Chester like?

A vacation rental is a private property you can stay in for a long or short time in Chester. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.