Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Chester

Fridge, microwave, oven, stovetop
Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park

Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park

Waynoka
10.0 out of 10, Exceptional, (9)
"The house is in a great location. Close to access road to the dunes. Plenty of parking."
United States
Jim V.
Escape to Waynoka: Your Ultimate 4-Bedroom Retreat Near Little Sahara State Park
Interior
The Ash Street Stables Villas

The Ash Street Stables Villas

Waynoka
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
Nov 16 - Nov 17
Total with taxes and fees
The Ash Street Stables Villas
Terrace/patio
Just Dune It - East

Just Dune It - East

Waynoka
9.8 out of 10, Exceptional, (52)
"Great place...very clean, great parking, great dune access. Wonderful hosts! Will definitely stay again!"
United States
Mark Y.
Just Dune It - East
Smart TV
Red Barn close to lake

Red Barn close to lake

Longdale
10.0 out of 10, Exceptional, (1)
"Relaxing!!!"
United States
Roy M.
Red Barn close to lake
Fridge, microwave, oven, stovetop
Casual Comfort for Duners, Hunters, and Normal Folks

Casual Comfort for Duners, Hunters, and Normal Folks

Waynoka
10.0 out of 10, Exceptional, (40)
"Great place to stay! "
United States
David S.
$215 nightly
The price is $249
Nov 16 - Nov 17
Total with taxes and fees
Casual Comfort for Duners, Hunters, and Normal Folks
Terrace/patio
Just Dune It - West

Just Dune It - West

Waynoka
10.0 out of 10, Exceptional, (47)
"Rented both housing units due to large group. Accommodations were amazing. Number one place to stay in waynoka. Rocky treats you like family. "
United States
Brian H.
Just Dune It - West
Outdoor dining
Fun Cabin in the Woods

Fun Cabin in the Woods

Longdale
9.6 out of 10, Exceptional, (4)
"Nice place well stocked. Loved the outdoor area. "
United States
bart b.
Fun Cabin in the Woods
Interior
The Ash Street Stables Villas

The Ash Street Stables Villas

Waynoka
9.6 out of 10, Exceptional, (15)
"The unit slept 12 but not enough towels, cookware, glassware or eating utensils for even the 7 of us. There were no linens for the sleeper sofa, the top of the mattresses on the bottom bunks were only 12 inches off the ground. and maytresses not that great. No extra dish soap, soap or shampoo. 2 kitchen towels only. Thecounters and floor weresticky when we went in. The only 12 inces off"
United States
Tammy G.
$571 nightly
The price is $661
Nov 16 - Nov 17
Total with taxes and fees
The Ash Street Stables Villas
Fridge, microwave, oven, stovetop
Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6.

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

Waynoka
9.8 out of 10, Exceptional, (20)
"The check in was easy as well as check out. The door has a code lock so you dont have to keep up with keys. Snacks extra toothbrush bath stuff was a nice extra touch in case you forget it"
United States
Samantha N.
$319 nightly
The price is $370
Nov 15 - Nov 16
Total with taxes and fees
Nancy Mae’s Cottage your home away from home, it’s all you need. Sleeps 6.
Dining
COZY CANTON GETAWAY 3 Bedroom/2 Bath Near Canton Lake With Extra Parking!

COZY CANTON GETAWAY 3 Bedroom/2 Bath Near Canton Lake With Extra Parking!

Canton
9.6 out of 10, Exceptional, (4)
"Host was friendly; property clean and comfortable!"
United States
JoAnn P.
COZY CANTON GETAWAY 3 Bedroom/2 Bath Near Canton Lake With Extra Parking!
Fridge, microwave, oven, stovetop
The Gifted Stay @ Seiling - 3BR/2BA In The Heart of Western Oklahoma!

The Gifted Stay @ Seiling - 3BR/2BA In The Heart of Western Oklahoma!

Seiling
10.0 out of 10, Exceptional, (1)
"Very nicehome. "
United States
Shelley B.
The Gifted Stay @ Seiling - 3BR/2BA In The Heart of Western Oklahoma!
Fridge, microwave, oven, stovetop
Spacious Lake Retreat 3BR Home Near Canton Lake w/ Huge Living Room Boat Parking

Spacious Lake Retreat 3BR Home Near Canton Lake w/ Huge Living Room Boat Parking

Canton
10.0 out of 10, Exceptional, (2)
"Friendly host; clean and comfortable"
United States
JoAnn P.
Spacious Lake Retreat 3BR Home Near Canton Lake w/ Huge Living Room Boat Parking
Outdoor dining
IV Rozes Ranch Charming 3-bedroom country house with AC and WiFi in Longdale.

IV Rozes Ranch Charming 3-bedroom country house with AC and WiFi in Longdale.

Longdale
10.0 out of 10, Exceptional, (2)
"Bryon is a great host and has a great place for you to stay if you’re looking for somewhere in the Canton/Longdale area. We had 5 in our group and had more than enough room. Bryon’s place has all the amenities as if you were at your own home. There is a great back porch area and large living room with a pool table and multiple couches for everyone to hang out. Bryon was very easy to get ahold of and very helpful with whatever questions I had."
United States
Michael W.
IV Rozes Ranch Charming 3-bedroom country house with AC and WiFi in Longdale.
House, 2 Bedrooms, Patio | Property grounds
Family Friendly Site With 24 Hour Access to Dunes

Family Friendly Site With 24 Hour Access to Dunes

2.0 star property
Waynoka
10.0 out of 10, Exceptional, (1)
"Very clean and had everything we needed. Ample parking for your trailer and buggies. Direct access to the dunes! Friendly little town. Owners were friendly and will definitely stay there again next time! "
United States
Amber
Family Friendly Site With 24 Hour Access to Dunes
Exterior detail
Hoot Owl Cabin: weekly discount $$ available!

Hoot Owl Cabin: weekly discount $$ available!

Longdale
Hoot Owl Cabin: weekly discount $$ available!
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.
View all properties
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

The Ash Street Stables Villas

The Ash Street Stables Villas

10/10 Excellent
"Clean, easy communication. "
Eric D. 3-night trip
Posted 8 days ago
The Ash Street Stables Villas

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?

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.