Chester Vacation Rentals

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Chester

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

5.6 out of 10, (9)
"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."
$170 nightly
The price is $183
Jul 16 - Jul 17
Total includes taxes and fees
Cozy house / small town living. Attractions include trout capital of Minnesota

Sage Street Retreat, a quiet and relaxing getaway

10.0 out of 10, Exceptional, (5)
"We really were happy with everything about our stay. Very clean & good beds & quiet neighborhood. Would definitely book again."
$206 nightly
The price is $216
Jul 16 - Jul 17
Total includes taxes and fees
Sage Street Retreat, a quiet and relaxing getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Lots of charm and only blocks away from the Root River and Bike trails: This vacation 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 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 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.