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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chester vacation rentals

A hotel room with a bed, a TV mounted on the wall, and a wooden dresser.

1. King Bed Non-Smoking

King Bed Non-Smoking
Seiling, OK
10.0 out of 10, Exceptional, (96 reviews)
"Loved the cozy atmosphere here!"
United States
Anonymous traveler
$54 nightly
The price is $59
Oct 2 - Oct 3
Total with taxes and fees
King Bed Non-Smoking
A hotel room with two beds, a small table, a chair, and a heater.

2. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Seiling, OK
10.0 out of 10, Exceptional, (82 reviews)
"Great value for what you get. Comfy beds and free parking helped us enjoy our stay more without overspending."
United States
Anonymous traveler
$56 nightly
The price is $62
Oct 3 - Oct 4
Total with taxes and fees
2 Queen Beds Non-Smoking
A hotel room with a bed, a TV mounted on the wall, and a wooden dresser.

3. Accessible King Bed|Seiling, OK

Accessible King Bed|Seiling, OK
Seiling, OK
10.0 out of 10, Exceptional, (80 reviews)
"Clean rooms made the stay so much easier!"
United States
Anonymous traveler
$52 nightly
The price is $56
Oct 2 - Oct 3
Total with taxes and fees
Accessible King Bed|Seiling, OK
A wooden porch with a stone wall, a blue door, and outdoor furniture.

4. Casual Comfort for Duners, Hunters, and Normal Folks

Casual Comfort for Duners, Hunters, and Normal Folks
Waynoka
10.0 out of 10, Exceptional, (46 reviews)
"Very clean and friendly and very nice people"
United States
NATE W.
$215 nightly
The price is $249
Oct 4 - Oct 5
Total with taxes and fees
Casual Comfort for Duners, Hunters, and Normal Folks
A compact kitchen with dark wooden cabinets, a black refrigerator, a microwave, and a stove. There is a dining table with four chairs and a decorative vase.

5. Just Dune It - East Home

Just Dune It - East Home
Waynoka
10.0 out of 10, Exceptional, (62 reviews)
"Always a great stay."
United States
Chad
$332 nightly
The price is $384
Oct 4 - Oct 5
Total with taxes and fees
Just Dune It - East Home
A living room with a dark brown sofa, a wooden coffee table, a wooden rocking chair, a black armchair, a small table with a lamp, and a painting on the wall.

6. 3-bedroom house in delightful Waynoka with cool AC breeze

3-bedroom house in delightful Waynoka with cool AC breeze
Waynoka
10.0 out of 10, Exceptional, (1 review)
"Great property and communication"
United States
John W.
$398 nightly
The price is $461
Oct 5 - Oct 6
Total with taxes and fees
3-bedroom house in delightful Waynoka with cool AC breeze
A gravel bed with blue crystals, a metal structure, and a building with a metal roof.

7. The Ash Street Stables Villas

The Ash Street Stables Villas
Waynoka
9.6 out of 10, Exceptional, (18 reviews)
"Nice worked great for the guys"
United States
Amy C.
$513 nightly
The price is $594
Oct 5 - Oct 6
Total with taxes and fees
The Ash Street Stables Villas
A concrete structure with blue glass pieces, surrounded by gravel and wooden planks.

8. The Ash Street Stables Villas

The Ash Street Stables Villas
Waynoka
10.0 out of 10, Exceptional, (9 reviews)
"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
Oct 4 - Oct 5
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

Fairview Inn

Fairview Inn

10/10 Excellent
"Front desk was welcoming and friendly. Room was clean and comfy. Will stay again."
Amanda 1-night trip
Posted 5 days ago
Fairview Inn

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 $56 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?

Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park: Visitors like this Chester vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.