Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Waynoka
4.91 out of 5 average rating, 127 reviews

Gather here! Nice home. 3-1/2 miles to the Dunes

Relax after a day at the dunes in this quiet home at the edge of town. It's a 3-1/2 mile drive to the dunes. With a permit from the city, you can drive your ATV right to the park! This two-bedroom, one-bath home has excellent central air and heat and ceiling fans. One bedroom offers a queen bed and the second has two twin beds. The sofa opens into a queen-size bed. We added a new stackable washer and dryer—perfect for small loads. Plenty of parking in the back for your truck, trailer, and ATV.

Top guest favorite
Farm stay in Sharon
5 out of 5 average rating, 38 reviews

Refurbished dairy barn on Shady Elm Farm.

This property is a remodeled dairy barn that is 750 sq ft with 10ft ceilings. The remodel was done with high end materials & has hardwood floors everywhere but the bathroom. Floor to ceiling cabinetry make this great for longer stays. We lived in it for 3 years with no problem! It has a built in king-sized bed. New washer/dryer unit installed for you! Get away from the hustle bustle of city living & enjoy the fresh country air & quiet environment. You'll love the covered patio and parking!

Top guest favorite
The spacious cabin exterior is illuminated at dusk, highlighting its rustic wooden structure. A well-maintained lawn is visible, bordered by outdoor lighting, while seating areas are set under the covered porch, offering a welcoming place to relax outdoors.
Cabin in Mooreland
5 out of 5 average rating, 10 reviews

Cabin on the 80

Escape to this unique and peaceful getaway. Relax and enjoy plenty of privacy in our charming modern rustic cabin. With a cozy welcoming atmosphere, this cabin is the perfect place to unwind and create lasting memories. In addition to fresh air and beautiful views, enjoy cozy evenings under the stars, hang out around the fire pit, do some grilling in the outdoor cooking area or enjoy gathering in the silo for fun and entertainment. Get refreshed in the outdoor shower and unique outhouse.

Top guest favorite
An aerial view captures a sprawling rural property featuring a modern house with a large lawn, surrounded by trees. Outbuildings are positioned nearby, with a solar panel system prominently displayed on the ground. The expansive landscape extends into the horizon, showcasing the serene country setting.
Farm stay in Mooreland
4.95 out of 5 average rating, 84 reviews

Grandma and Grandpa's Country Home

The Old Wolf House, where I live is a Historical, Oklahoma site. This area was settled right before the land run and this house is extremely old and hard to live in. It is haunted, It has issues with almost everything that is modern and I do believe the old soul of the house rejects and destroys anything modern. I LOVE IT! Don't worry that is not where you will be staying. My parents retired in 2003 and built a nice place right behind the old Wolf House. All modern and nice!

Guest favorite
A sectional couch with black and white accent pillows is positioned around a rustic wooden coffee table. Two wall art pieces featuring bold lettering are displayed above the seating area. A window allows natural light to brighten the space, which is complemented by a patterned floor.
Home in Waynoka
4.9 out of 5 average rating, 255 reviews

After Dune Delight - Ride Straight to the Dunes!

Come and go at your leisure! Ride straight to the dunes from After Dune Delight. Stay with us at this 4 bedroom, 2 bathroom house near the 24 hour trail. With one queen bed in each bedroom, you can sleep 8 comfortably. Curl up on the sectional couch and watch your favorite shows on Netflix and Hulu if you need a break from the dunes. There is parking in the front yard and fenced backyard. Hit "see more" for more information about staying with us! *PET FEE REQUIRED*

Guest favorite
An entrance to a barndominium is depicted, with a metal exterior and a white door framed by wooden beams. A rustic bench made of reclaimed wood sits nearby, accompanied by a propane grill positioned next to it. Two small windows allow natural light to enter.
Ranch in Seiling
4.91 out of 5 average rating, 55 reviews

Brae Ranch - Getaway & Enjoy The Outdoors

Looking to get away from the city? At Brae Ranch you can get away from it all. Stay in a barndominium all to yourself. Check out our newly updated kitchen, bathroom, and living room! We are located in NW Oklahoma with canyons all around and a view that goes for miles. Our private 1000 acre ranch has hiking trails throughout and a beautiful fishing pond. During your stay you can also signup for a fishing or hunting experience!! Message us for more details.

Superhost
A charming brick home with a sloped roof is situated in a spacious yard. Two dogs are seen in the foreground, with a driveway leading to an attached garage. A fenced yard is visible in the background, providing a sense of privacy.
Home in Vici
4.81 out of 5 average rating, 32 reviews

Brick Home with Large Backyard

This charming brick home is in a peaceful neighborhood on the edge of town. The large, fenced back yard offers a private and secure place for you and your pets to enjoy. The home features central heat and air, TVs in the bedrooms, plus a 70" TV in the living room for your entertainment. The kitchen and laundry room provide all the essentials. Though the appliances and carpets are original, they add to the home’s unique character and cozy atmosphere.

Top guest favorite
The kitchen features a modern layout with light cabinetry and a large island, equipped with multiple seating options. Stainless steel appliances complement the design, while pendant lighting adds illumination over the workspace. A textured backsplash adds visual interest above the countertops.
Home in Woodward
4.99 out of 5 average rating, 276 reviews

Meadowview House

Fully renovated home in a great location! Fall in love with the open floor plan, gorgeous kitchen, and covered patio. The fenced in backyard gives you some privacy to enjoy your evenings with your other guests, or even for some "alone time" to read or work outside. Everything in this home has been redone, so it should be a worry-free experience! Enjoy old school gaming and cornhole while you are here!!

Superhost
An outdoor deck area features overhead string lights illuminating the space. Seating options include benches and tables arranged around a central fire pit. The wooden structure is surrounded by rustic wooden railings and trees, creating a secluded and inviting atmosphere.
Cabin in Waynoka
4.89 out of 5 average rating, 36 reviews

Mirage 1

Rustic cabin hideaway on Little Sahara Sand trail. 2 bedroom, 1 bath with full kitchen. Outdoor lighted deck with fire pit and grill. Private road with plenty of parking. No need to trailer your ORV, Direct access to the trail from the property.

Guest favorite
A single-story house with a light-colored exterior is visible, complemented by a set of steps leading to the entrance. Three windows framed in white are arranged symmetrically at the front, with a small brick planter bordered by grass in the foreground.
Home in Fairview
4.89 out of 5 average rating, 47 reviews

Cozy retreat

Take it easy at this unique and tranquil getaway. This place does not have a TV but does have Wi-Fi. It's located a few blocks from the hospital and nursing home. And is fairly close to a grocery store.

Superhost
A full-size pool table occupies the center of a spacious room, with a set of colorful billiard balls arranged on the green felt. Natural light enters through large windows, illuminating the surrounding seating area with a mix of striped cushions and soft furnishings.
Vacation home in Longdale
4.84 out of 5 average rating, 31 reviews

Canton Lake 58 Escape

Bring the whole family or work crew to this great place with lots of Games and entertainment and large rooms for fun and Relaxing

Top guest favorite
A shaded outdoor patio area is visible, featuring two wooden chairs and a small table. The surrounding trees provide natural cover, while a bright wall and windows enhance the inviting space. A grill can be seen in the background, completing the tranquil setting.
Cabin in Carmen
5 out of 5 average rating, 21 reviews

Byrd Homestead - Get Away

Take it easy at this unique and tranquil getaway. Retreat into nature, surrounded by wildlife.

Popular amenities for Chester vacation rentals

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  2. United States
  3. Oklahoma
  4. Major County
  5. Chester