Book Hotels in Chester, IA

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Chester hotels

Quiet, comfortable bed & breakfast in a gorgeous rural setting!

Quiet, comfortable bed & breakfast in a gorgeous rural setting!

Spring Valley MN
$125 nightly
The price is $134 total per night from Nov 12 to Nov 13
$134 total
Nov 12 - Nov 13
Total with taxes and fees
This bed & breakfast includes a garden and barbecue grills.
"We loved the clean unit in the beautiful & quiet setting! We loved playing pool on the great table. The owners are so helpful & easy to talk to. The breakfast was delicious—especially the homemade cinnamon rolls!"

Reviewed on Nov 9, 2026

Opens in a new windowQuiet, comfortable bed & breakfast in a gorgeous rural setting!
Lots of charm and only blocks away from the Root River and Bike trails

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

Preston MN
This vacation home includes a garden and laundry facilities.
"."

Reviewed on Nov 1, 2026

Get rates
Opens in a new window Lots of charm and only blocks away from the Root River and Bike trails
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 Nov 15 to Nov 16
$82 total
Nov 15 - Nov 16
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 ...
"room was clean, staff was very helpful, the breakfast was a little under whelming. it was very basic."

Reviewed on Nov 3, 2026

Opens in a new windowSuper 8 by Wyndham Cresco IA
Western Inn & Suites

Western Inn & Suites

2 out of 5
1530 Main St, Osage IA
$60 nightly
The price is $67 total per night from Nov 10 to Nov 11
$67 total
Nov 10 - Nov 11
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 ...
"It was clean and convenient. Staff was helpful although hard to understand."

Reviewed on Nov 9, 2026

Opens in a new windowWestern Inn & Suites
Steps to Root River: Home w/ Large Yard!

Steps to Root River: Home w/ Large Yard!

Preston MN
This vacation home includes a garden and laundry facilities.
"I want my money back. This place is not like the picture. There were bugs everywhere, even in the bed! The shower was full of hair in the mat and wouldn't drain. I had to clean everything before using it.The dishes were dirty the floors were dirty the worst experience I've had."

Reviewed on Sep 9, 2026

Get rates
Opens in a new windowSteps to Root River: Home w/ Large Yard!
AmericInn by Wyndham Osage

AmericInn by Wyndham Osage

3 out of 5
2212 Highway 218 Osage IA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Dec 6 to Dec 7
$113 total
Dec 6 - Dec 7
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 ...
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 Nov 10 to Nov 11
$140 total
Nov 10 - Nov 11
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. ...
Opens in a new windowCountry Trails Inn & Suites
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
$79 nightly
The price is $87 total per night from Nov 12 to Nov 13
$87 total
Nov 12 - Nov 13
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 ...
Opens in a new windowAmericas Best Value Inn & Suites Spring Valley
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 Nov 10 to Nov 11
$168 total
Nov 10 - Nov 11
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Opens in a new windowCountry Lodge inn
Don't see what you're looking for?
See all available properties in Chester
View all properties
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 $67. 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 24 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

Quiet, comfortable bed & breakfast in a gorgeous rural setting!

Quiet, comfortable bed & breakfast in a gorgeous rural setting!

5 out of 5
Posted 12 hours ago
Travelocity Verified Review
"We loved the clean unit in the beautiful & quiet setting! We loved playing pool on the great table. The owners are so helpful & easy to talk to. The breakfast was delicious—especially the homemade cinnamon rolls!"
A verified traveler stayed at Quiet, comfortable bed & breakfast in a gorgeous rural setting!
Quiet, comfortable bed & breakfast in a gorgeous rural setting!