Chester Vacation Rentals

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Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Chester vacation rentals

Fridge, microwave, oven, stovetop
Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6.

Vacation Home in Waynoka

Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6.
10.0 out of 10, Exceptional, (22)
"The house was perfect! Newly remodeled bathroom and close to the dunes! We had an issue getting into the house but Miss Kathy was ON IT, and it was resolved immediately!!We will definitely stay again when we go to ride!"
United States
Ronee K.
$315 nightly
The price is $365
Dec 30 - Dec 31
Total with taxes and fees
Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6.
Fridge, microwave, oven, stovetop
Casual Comfort for Duners, Hunters, and Normal Folks

Mobile Home in Waynoka

Casual Comfort for Duners, Hunters, and Normal Folks
10.0 out of 10, Exceptional, (40)
"Enjoyed our stay here. It’s cozy, clean, and conveniently located! We will be back!"
United States
Karly W.
$215 nightly
The price is $249
Dec 31 - Jan 1, 2026
Total with taxes and fees
Casual Comfort for Duners, Hunters, and Normal Folks
Terrace/patio
Just Dune It - East

Mobile Home in Waynoka

Just Dune It - East
9.8 out of 10, Exceptional, (53)
"We really enjoy staying here. Great location."
United States
John M.
$254 nightly
The price is $294
Dec 30 - Dec 31
Total with taxes and fees
Just Dune It - East
Interior
The Ash Street Stables Villas

Villa in Waynoka

The Ash Street Stables Villas
10.0 out of 10, Exceptional, (8)
"This is the best place to stay in the entire town. We were definitely impressed with everything. If you are looking for a place to stay this is definitely the best place! "
United States
Brian R.
$1,165 nightly
The price is $1,349
Dec 31 - Jan 1, 2026
Total with taxes and fees
The Ash Street Stables Villas
Interior
The Ash Street Stables Villas

Vacation Home in Waynoka

The Ash Street Stables Villas
9.6 out of 10, Exceptional, (16)
"Great place to stay. "
United States
Tyler H.
$571 nightly
The price is $661
Dec 30 - Dec 31
Total with taxes and fees
The Ash Street Stables Villas
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.
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Top Chester Hotel Reviews

Best Western Plus Fairview Inn & Suites

Best Western Plus Fairview Inn & Suites

10/10 Excellent
"Good"
Santos 1-night trip
Posted 1 month ago
Best Western Plus Fairview Inn & Suites

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $249 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we offer vacation rentals near the most popular points of interest in Chester, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Chester has to offer?

Red Barn close to lake: Visitors like this Chester vacation home rental. It is located on a lake and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can stay in for a short or long stay in Chester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for small groups.