Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

The front entrance features a decorative door with a stained glass window, accompanied by a mailbox and a welcoming sign that reads 'GATHER here.' The house showcases a combination of textured stone and wood paneling, creating an inviting exterior.

Home in Waynoka

4.91 out of 5 average rating, 113 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

A charming exterior of a single-story home features a covered front porch with two chairs and a table. A garage door is visible on the left, while green grass and seasonal leaves surround the pathway. A vibrant blue door adds a touch of color to the warm-toned façade.

Bungalow in Cherokee

4.93 out of 5 average rating, 151 reviews

"Crazy Cat Lady House" 2 bedroom newly remodeled.

Relax with your family at this peaceful place to stay. Pet friendly with large back yard and large front awning where you can enjoy beautiful sunsets or a morning cup of coffee. Cherokee is a small town with two restaurants, a subway, and quick stop. This home is located in a quiet neighborhood and a quiet town close to the Salt Plains National Wildlife Refuge which provides birding, and beautiful views. There are many other interesting sites within a short drive; the perfect getaway.

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

4.94 out of 5 average rating, 66 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 charming farmhouse is depicted, featuring a light-colored exterior with a metal roof. Large windows allow natural light to fill the interior, while a small porch with seating is visible at the front. The surrounding grassy area blends with the clear blue sky.

Home in Vici

4.88 out of 5 average rating, 42 reviews

Double A Ranch guest house, hunters welcome!

This 100+ year old farm house has 2 bedrooms and 1 bathroom with a large shower. Both bedrooms have queen size beds. Central living room has lots seating and 42" tv. The home also has fully equipped kitchen and laundry rooms and 2 enclosed porches, one is an entry/mud room, but the other could be used as extra sleeping or activity space. Home has central heat and air, with the exception of the porches. Original hardwood floors in living and bedrooms with a lot of character!

Superhost

A well-appointed bedroom features a spacious bed with a cozy quilt in neutral tones. Decorative wall art in simple frames is mounted above the bed. A closet with sliding doors is visible, along with an area rug that adds texture to the wooden floor.

Farm stay in Chester

4.85 out of 5 average rating, 132 reviews

Farmhouse on acreage - Secluded, Cozy, & Modern

Stay at our family farmhouse situated in a grassy meadow in beautiful northwest Oklahoma. Built in the early 1900's, this home has been completely renovated for modern comfort. With acres to explore, you'll witness the ranch at work with cattle grazing, wildlife abounding with deer and quail, and native grasses and flowers flourishing. Inside the home you will find two well-appointed bedrooms, a large loft, an open main room floor plan with a well equipped kitchen.

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

4.91 out of 5 average rating, 223 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

4.9 out of 5 average rating, 42 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

4.86 out of 5 average rating, 22 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

A single-story home is displayed, featuring a white exterior with black accents. A paved driveway leads to a garage on the left. A well-manicured lawn surrounds the house, with small shrubs positioned near the front. The entrance is indicated by a light fixture mounted above the door.

Home in Woodward

4.99 out of 5 average rating, 255 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!!

Top guest favorite

A spacious wooden deck offers views of expansive green fields and scattered trees under a cloudy sky. The railing provides safety while emphasizing the openness of the surrounding landscape.

Farm stay in Geary

4.87 out of 5 average rating, 283 reviews

Historic Schoolhouse Cabin | Stargazing Spot

Sleep in a renovated one-room schoolhouse on a working farm—just off HWY 281 and 15 mins from I-40 & Route 66. Stargaze, spot deer, fish the pond, shower under the sky (yes, really), and unwind by the fire pit. It’s peaceful, private, and a little offbeat—just how we like it. Great for couples or solo folks who need a break from the noise. Read the full listing & check pics before booking!

Top guest favorite

A modern kitchen features dark cabinetry and stainless steel appliances. Countertops are accented by a bowl of fresh lemons and decorative placemats. An open layout is highlighted by a light fixture overhead, providing ample workspace for cooking and meal preparation.

Home in Seiling

5 out of 5 average rating, 7 reviews

The Gifted Stay @ Seiling, OK

The Gifted Stay @ Seiling is a cozy 3-bedroom, 2-bath home perfect for families or small groups. Enjoy a beautiful kitchen, spacious living area, and a central location in Northwest Oklahoma. Explore nearby attractions like Canton Lake, Little Sahara, Gloss Mountains, Boiling Springs, and Great Salt Plains. Comfort, convenience, and adventure await!