Find hotels in Chester, IA from $65

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester hotels

Comfort Inn & Suites Rochester South Mayo Clinic

Comfort Inn & Suites Rochester South Mayo Clinic
2.0 star property
Rochester
8.8 out of 10, Excellent, (1,000 reviews)
"Spacious clean room. Friendly staff. Breakfast area was kind of a mess. We went down at 830 amd there was very little food left and the area was super messy."
United States
Linda
$63 nightly
The price is $73
May 9 - May 10
Total with taxes and fees
Comfort Inn & Suites Rochester South Mayo Clinic

AmericInn by Wyndham Osage

AmericInn by Wyndham Osage
2.5 star property
Osage
9.6 out of 10, Exceptional, (282 reviews)
"Room was clean and at good room temperature despite the bitter cold (outside) conditions. friendly and welcoming staff "
United States
Marc
$97 nightly
The price is $109
Apr 26 - Apr 27
Total with taxes and fees
AmericInn by Wyndham Osage

Stone Mill Hotel & Suites

Stone Mill Hotel & Suites
3.0 star property
Lanesboro
9.2 out of 10, Wonderful, (670 reviews)
"Heather at the front desk gave terrific customer service Her knowledge of the town and places to eat made our stay that much more enjoyable. The owner Ann has done a wonderful job in running the hotel. Her friendliness and out going personality is top notch! Kudos to both of you ! "
United States
John
$105 nightly
The price is $113
Apr 9 - Apr 10
Total with taxes and fees
Stone Mill Hotel & Suites

America's Stay Inn Stewartville

America's Stay Inn Stewartville
2.5 star property
Stewartville
8.0 out of 10, Very Good, (430 reviews)
"Good price, clean room."
United States
Susan
$56 nightly
The price is $60
Apr 14 - Apr 15
Total with taxes and fees
America's Stay Inn Stewartville

Country Trails Inn & Suites

Country Trails Inn & Suites
2.0 star property
Preston
9.4 out of 10, Exceptional, (107 reviews)
"We all had fun in the pool and the hot tub Breakfast was good wasnt packed in there could actually sit in there and eat or go outside and eat at the pinic table. Staff was great"
United States
Angela
$126 nightly
The price is $140
Apr 9 - Apr 10
Total with taxes and fees
Country Trails Inn & Suites

Super 8 by Wyndham New Hampton

Super 8 by Wyndham New Hampton
2.0 star property
New Hampton
8.6 out of 10, Excellent, (386 reviews)
"Breakfast good "
United States
Stephen
$88 nightly
The price is $99
May 3 - May 4
Total with taxes and fees
Super 8 by Wyndham New Hampton

Americas Best Value Inn & Suites Spring Valley

Americas Best Value Inn & Suites Spring Valley
2.0 star property
Spring Valley
8.2 out of 10, Very Good, (442 reviews)
"Nice & quiet. Comfortable room& great location. Desk pleasant "
United States
Jodi
$78 nightly
The price is $86
May 3 - May 4
Total with taxes and fees
Americas Best Value Inn & Suites Spring Valley

Super 8 by Wyndham Cresco IA

Super 8 by Wyndham Cresco IA
2.0 star property
Cresco
8.6 out of 10, Excellent, (499 reviews)
"Very clean with friendly staff"
United States
Alexis
$74 nightly
The price is $83
Apr 14 - Apr 15
Total with taxes and fees
Super 8 by Wyndham Cresco IA

Green Gables Inn

Green Gables Inn
2.0 star property
Lanesboro
9.6 out of 10, Exceptional, (74 reviews)
"The stay was wonderful and will definitely return. "
United States
Gerilyn
$103 nightly
The price is $110
Apr 9 - Apr 10
Total with taxes and fees
Green Gables Inn

Country Lodge inn

Country Lodge inn
2.0 star property
Harmony
9.0 out of 10, Wonderful, (40 reviews)
"Old motel but clean, with friendly owners."
United States
Fred
$146 nightly
The price is $161
Apr 9 - Apr 10
Total with taxes and fees
Country Lodge inn

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

Quiet, comfortable bed & breakfast in a gorgeous rural setting!
Spring Valley
10.0 out of 10, Exceptional, (98 reviews)
"Great breakfast, super comfortable bed! The hosts were very friendly and it was a wonderful visit."
United States
Ryan K.
$133 nightly
The price is $142
Apr 9 - Apr 10
Total with taxes and fees
Quiet, comfortable bed & breakfast in a gorgeous rural setting!

Room 4: Sleep Where Prohibition Secrets Were Made - Historic Escape!

Room 4: Sleep Where Prohibition Secrets Were Made - Historic Escape!
Spillville
10.0 out of 10, Exceptional, (4 reviews)
"Great value. Comfy bed & great water pressure i"
United States
Melanie S.
$115 nightly
The price is $121
Apr 9 - Apr 10
Total with taxes and fees
Room 4: Sleep Where Prohibition Secrets Were Made - Historic Escape!

Western Inn & Suites

Western Inn & Suites
2.0 star property
Osage
6.2 out of 10, (58 reviews)
"It was very good for the price."
United States
Khalid
$58 nightly
The price is $65
Apr 9 - Apr 10
Total with taxes and fees
Western Inn & Suites

Charming farmhouse with 4 bedrooms and WiFi, AC near Spring Valley

Charming farmhouse with 4 bedrooms and WiFi, AC near Spring Valley
SPRING VALLEY
10.0 out of 10, Exceptional, (1 review)
"House was clean and everything was in great condition. Planning on staying again. "
United States
William Sylvester S.
$291 nightly
The price is $312
Apr 12 - Apr 13
Total with taxes and fees
Charming farmhouse with 4 bedrooms and WiFi, AC near Spring Valley

Taylor Made Bed and Breakfast

Taylor Made Bed and Breakfast
3.0 star property
Spillville
10.0 out of 10, Exceptional, (4 reviews)
"Property was all decked out for Christmas! We were greeted by the owners, room so comfy and warm and in winter in Iowa that's important, fresh delicious breakfast too!"
United States
Anonymous traveler
Taylor Made Bed and Breakfast

Oak Meadow Farmhouse

Oak Meadow Farmhouse
Spring Valley
9.8 out of 10, Exceptional, (15 reviews)
"Great area, Midwest charm"
United States
Larry H.
$279 nightly
The price is $300
Apr 9 - Apr 10
Total with taxes and fees
Oak Meadow Farmhouse

*CLOSED FOR 2026 SEASON* Schmidt Farm: an interactive farm experience

*CLOSED FOR 2026 SEASON* Schmidt Farm: an interactive farm experience
Preston
10.0 out of 10, Exceptional, (97 reviews)
"A very unique getaway perfect for families with young children."
United States
Bonnie E.
*CLOSED FOR 2026 SEASON* Schmidt Farm: an interactive farm experience

Room 2: Sleep Where Prohibition Secrets Were Made - Historic Escape!

Room 2: Sleep Where Prohibition Secrets Were Made - Historic Escape!
Spillville
9.0 out of 10, Wonderful, (2 reviews)
"Unique and cool place to stay, very convenient having food and drink just downstairs. Can’t beat it for the price. "
United States
Dan D.
$125 nightly
The price is $131
Apr 9 - Apr 10
Total with taxes and fees
Room 2: Sleep Where Prohibition Secrets Were Made - Historic Escape!

Valley Farmhouse

Valley Farmhouse
Spring Valley
4.8 out of 10, (5 reviews)
"Dan was super nice and accommodating. If you are looking for a 5 star hotel, look elsewhere. It you want a large, clean farmhouse, this place is for you. Being a working family farm, expect to see a tractor or two going in and out. We really enjoyed sitting on the wrap around porch with a book watching the cows. Lilly, the family's dog, was super friendly and may come to visit you. We will definitely go back! Thanks again Dan!"
United States
Kim A.
$229 nightly
The price is $246
Apr 10 - Apr 11
Total with taxes and fees
Valley Farmhouse

Room A1 at Green Gables Inn - Garden Rooms on the Riverside in Lanesboro, MN

Room A1 at Green Gables Inn - Garden Rooms on the Riverside in Lanesboro, MN
Lanesboro
Room A1 at Green Gables Inn - Garden Rooms on the Riverside in Lanesboro, MN
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

Top Chester Hotel Reviews

More cheap stays in Chester

Hotels in Chester with star-rating

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is the downtown area, particularly around Main Street, for its convenient access to local establishments and the town's central activities.

The downtown area of Chester is the heart of the community, characterized by its traditional main street layout. You'll find a selection of local businesses, eateries, and the town's historical landmarks concentrated here. This area is easily walkable and serves as a central point for exploring Chester.

Couples often find downtown Chester appealing for its relaxed pace and local charm. It provides a pleasant setting for strolls, enjoying local meals, and visiting town attractions like the Chester Historical Society Museum without needing to travel far. It's a nice setting for a quiet getaway.

For solo travelers, staying downtown offers the most convenient access to amenities and social opportunities within Chester.
When is the best time to go to Chester?
The best time to visit Chester, Iowa, is during the late spring (May to early June) and early autumn (September to October) when the weather is most pleasant.

Late spring offers mild temperatures, typically ranging from the 60s to low 70s Fahrenheit, making it ideal for outdoor activities like exploring the local park trails or visiting nearby farms. The landscape is lush and green, and local produce starts to become available in markets. This period is particularly good for families looking for comfortable weather for outdoor excursions.

Early autumn also provides comfortable temperatures, generally in the 60s, with lower humidity. The changing leaves create picturesque scenery, especially around the Upper Iowa River. This season is great for couples seeking a tranquil getaway, perhaps enjoying scenic drives or visiting local harvest festivals. The cooler evenings are also great for enjoying a meal at one of Chester's few dining spots.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a Chester hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Chester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from $65 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia