Book Hotels in Chester, IA

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Top Chester hotels

Wykoff Historical Jail Haus with Original Jail Cell Bunks.

Wykoff Historical Jail Haus with Original Jail Cell Bunks.

Wykoff MN
$115 nightly
The price is $123 total per night from Sep 8 to Sep 9
$123 total
Sep 8 - Sep 9
Total with taxes and fees
A garden is available at this vacation home.
"Absolutely love this property! It was out second time staying and we already have a return trip booked in a couple months!"

Reviewed on Aug 23, 2026

Opens in a new windowWykoff Historical Jail Haus with Original Jail Cell Bunks.
AmericInn by Wyndham Osage

AmericInn by Wyndham Osage

3 out of 5
2212 Highway 218 Osage IA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from Sep 27 to Sep 28
$121 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy ...
"Front desk check-in staff was amazing. Propped service great information told us everything we needed to know. Room was clean and very comfortable. Breakfast was good and staff at breakfast was very helpful. Thanks for a wonderful stay."

Reviewed on Aug 23, 2026

Opens in a new windowAmericInn by Wyndham Osage
Country Trails Inn & Suites

Country Trails Inn & Suites

2 out of 5
809 U.S. 52 Preston MN
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $140 total per night from Aug 30 to Aug 31
$140 total
Aug 30 - Aug 31
Total with taxes and fees
An attached winery and an indoor pool are featured at this smoke-free hotel. Enjoy the hot tub and free perks like continental breakfast and free self parking. ...
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Reviewed on Aug 27, 2026

Opens in a new windowCountry Trails Inn & Suites
Country Lodge inn

Country Lodge inn

2 out of 5
525 Main Ave N Harmony MN
$152 nightly
The price is $168 total per night from Aug 30 to Aug 31
$168 total
Aug 30 - Aug 31
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
"The rpm was clean and owner pleasant"

Reviewed on Aug 20, 2026

Opens in a new windowCountry Lodge inn
Super 8 by Wyndham Cresco IA

Super 8 by Wyndham Cresco IA

2 out of 5
511 Second Ave SE, Hwy 9 & 5th Street Cresco IA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Sep 20 to Sep 21
$82 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is ...
"Far exceeded what I thought staying at a Super 8 could be! I’ll be back next year to paddle another stretch of the Iowa River."

Reviewed on Aug 14, 2026

Opens in a new windowSuper 8 by Wyndham Cresco IA
Americas Best Value Inn & Suites Spring Valley

Americas Best Value Inn & Suites Spring Valley

2 out of 5
745 N Broadway St Spring Valley MN
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Sep 8 to Sep 9
$98 total
Sep 8 - Sep 9
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"Clean room, ççcccccccccccçccccccccccffffffffffghjhhh"

Reviewed on Aug 24, 2026

Opens in a new windowAmericas Best Value Inn & Suites Spring Valley
Valley Farmhouse

Valley Farmhouse

Spring Valley MN
$235 nightly
The price is $253 total per night from Sep 7 to Sep 8
$253 total
Sep 7 - Sep 8
Total with taxes and fees
A hot tub is featured at this farm stay, along with laundry facilities and barbecue grills.
Worst travel experience ever
"Our large family traveled to the property. Other people were staying there and we were turned away by the owner. Nothing was done to find ys a new place, so we turned around and drove home. It was a waste of time, money and gas. Nothing was done to make situation right."

Reviewed on Jul 29, 2024

Opens in a new windowValley Farmhouse
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St, Osage IA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Sep 4 to Sep 5
$78 total
Sep 4 - Sep 5
Total with taxes and fees
The motel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
Opens in a new windowWestern Inn & Suites
Cozy house / small town living. Attractions include trout capital of Minnesota

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

Preston MN
This vacation home features a garden, laundry facilities, and barbecue grills.
Get rates
Opens in a new windowCozy house / small town living. Attractions include trout capital of Minnesota
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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.

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Take some of the hassles out of traveling with little ones by opting for a family-friendly Chester hotel. From special amenities to more services, these stays feature perks that'll make your getaway smooth sailing: The whole team will enjoy staying at Sage Street Retreat, a quiet and relaxing getaway. A playground and animal viewing activities are just a couple of the things that help make this property a sought-after option. Super 8 by Wyndham Cresco IA is another excellent choice. After a big day of exploring, come home to your cozy room and perks like complimentary breakfast and pet-friendly facilities.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is $78. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 27 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during January, March and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as February, April and September.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

Country Trails Inn & Suites

Country Trails Inn & Suites

5 out of 5
Posted 1 day ago
Travelocity Verified Review
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A verified traveler stayed at Country Trails Inn & Suites
Country Trails Inn & Suites