Search Vacation Homes in Chester

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Vacation Homes in Chester

Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
Property grounds

Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!

10.0 out of 10, Exceptional, (23)
"The property was spotless and the location was perfect. Quiet, peaceful & not too far from town. "
Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
WATERFRONT HOME ON LAKE MADISON
Fridge, microwave, oven, stovetop

WATERFRONT HOME ON LAKE MADISON

10.0 out of 10, Exceptional, (26)
"Everything was great! Thank you!"
WATERFRONT HOME ON LAKE MADISON
Beautiful year round lake home! Sleeps 8 comfortably!
Fridge, microwave, oven, stovetop

Beautiful year round lake home! Sleeps 8 comfortably!

10.0 out of 10, Exceptional, (30)
"Great location overlooking the lake Nice environment Plenty of Room"
Beautiful year round lake home! Sleeps 8 comfortably!
The Grandview Lake House, Dog Friendly, Near Lake Madison, Outdoor Patio
Fridge, microwave, oven, stovetop

The Grandview Lake House, Dog Friendly, Near Lake Madison, Outdoor Patio

9.6 out of 10, Exceptional, (5)
"Great spot to stay if you want to be near a quiet little town. It’s also within driving distance of some cool South Dakota attractions!"
The Grandview Lake House, Dog Friendly, Near Lake Madison, Outdoor Patio
Beautiful large lake home for a family retreat, have fun by the water!
Terrace/patio

Beautiful large lake home for a family retreat, have fun by the water!

7.6 out of 10, Good, (4)
"Wonderful experience! The property was great! Pictures do not do it justice. Beautiful home, amazing deck for watching the water. Owners were great to work with. Highly recommend!"
Beautiful large lake home for a family retreat, have fun by the water!
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
Interior

Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.

9.2 out of 10, Wonderful, (48)
"Lots of room inside and plenty of parking space. Well arranged for a large group visiting and dining. Very noisy outside with almost constant traffic on Hwy 38. Could use some repairs and cleanup on the outside."
Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.
Sportsman's Outpost
2 bedrooms, free WiFi, bed sheets

Sportsman's Outpost

$145 nightly
The price is $155
Aug 13 - Aug 14
Total includes taxes and fees
Sportsman's Outpost
Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8
Fridge, microwave, oven, stovetop

Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8

10.0 out of 10, Exceptional, (4)
"Very pretty and relaxing!! Great for fishing swimming and making memories!"
Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8
Summit Splendor, a splendid place to stay while in Madison, SD
Microwave, oven, stovetop, dishwasher

Summit Splendor, a splendid place to stay while in Madison, SD

2.0 star property
10.0 out of 10, Exceptional, (5)
"Beautifully renovated home in a quiet neighborhood!"
Summit Splendor, a splendid place to stay while in Madison, SD
Welcome DSU, Aviation Students & Madison Families! Cute, Clean & Well Stocked!
Fridge, microwave, oven, stovetop

Welcome DSU, Aviation Students & Madison Families! Cute, Clean & Well Stocked!

10.0 out of 10, Exceptional, (5)
"We loved the layout of the house and how organized everything was inside the kitchen. It was perfect for our visit!"
Welcome DSU, Aviation Students & Madison Families! Cute, Clean & Well Stocked!
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
Sign in
Sign up, it's free

Top Chester Hotel Reviews

AmericInn by Wyndham Hartford SD

AmericInn by Wyndham Hartford SD

10/10 Excellent
"Friendly staff and clean. Enjoyed being in the countryside but close to the interstate. The surrounding farmland is beautiful. The only drawback was road construction which has nothing to do with the hotel! "
Anne 1-night trip
Posted 21 hours ago
AmericInn by Wyndham Hartford SD