Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Guest favourite
Home in Waynoka
4.91 out of 5 average rating, 121 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 favourite
The kitchen features rich wooden cabinetry and a spacious granite countertop island. Stainless steel appliances, including a microwave and a refrigerator, are visible. A tile backsplash complements the kitchen's sleek design, while natural light filters through the window, illuminating the workspace.
Farm stay in Sharon
5 out of 5 average rating, 36 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 favourite
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, 9 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 favourite
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, 80 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 favourite
The living area features a spacious sectional sofa adorned with decorative pillows, complemented by a round coffee table on a soft area rug. Natural light filters through a window, enhancing the neutral color palette. A simple artwork hangs on the wall, adding a touch of style.
Home in Woodward
4.97 out of 5 average rating, 76 reviews

Cozy 3BR | 5 Beds | Crews, Families & Long Stays

Welcome to your home away from home! This spacious 3-bedroom, 5-bed home is perfect for work crews, travelers, families, or small groups. Whether you're here for a few nights or a few weeks, this cozy space offers comfort, convenience, and everything you need for a relaxing stay. Sleeping Arrangements: • BR 1: Queen bed • BR 2: Queen bed • BR 3: 1 Single bed, 1 Double bed & 1 Sofa bed Ideal For: • Crews (oil & gas, wind, construction, etc.) • Families • Short or extended stays

Guest favourite
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
4.89 out of 5 average rating, 47 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!

Top guest favourite
A spacious living room features comfortable seating arranged around a central coffee table. Natural light enters through large windows, accompanied by a decorative clock on the wall. A cozy fireplace is situated below a television, creating a warm ambiance. A neutral color palette is present.
Home in Woodward
4.98 out of 5 average rating, 52 reviews

The Cozy Casa : Comfort Awaits!

3 bed/2 bath home in the heart of Woodward, Oklahoma. This comfortable retreat offers all the amenities you need for a relaxing stay. Enjoy the spacious living areas, fully equipped kitchen, and cozy bedrooms designed for a restful night's sleep. Convenient location, just minutes away from local attractions and outdoor activities. Our home provides the perfect base for all your Woodward adventures. Book your stay now and experience the comfort and convenience of our cozy haven!

Superhost
An inviting covered outdoor bar area features a wooden bar with several rattan stools arranged around it. Ceiling fans facilitate airflow, while additional seating options are present nearby. The space is surrounded by lush greenery, providing a serene backdrop for relaxation.
Home in Woodward
4.75 out of 5 average rating, 4 reviews

Spacious “El Cortez” home in town on two acres

Spacious 5 bed, 5 bath home on 2.5 acres in the heart of Woodward. With 4,200 square feet of living space there is room for the whole crew to spread out and relax. Enjoy quiet evenings on the back porch watching local wildlife. This clean well equipped home offers full amenities, fast Wi-Fi, and everything needed for a relaxing long-term stay. Centrally located and close to shops, dining and more. Perfect for families or traveling workers looking for comfort and convenience.

Top guest favourite
An open living area is showcased, featuring a brown leather couch with a colorful throw blanket. Wooden beams and a ceiling fan add to the space. Mounted deer heads decorate the walls, while large windows allow ample natural light, illuminating the wooden dining area nearby.
Home in Taloga
4.95 out of 5 average rating, 20 reviews

Stidham’s Cabin

Relax with family or friends at our peaceful country cabin. There is an abundance of cattle, horses and wildlife from your back porch view. This cabin is located 3 miles from town with access to the South Canadian River! It is a 3 bedroom, 2 bath home with 7 beds that sleep 12 people comfortably. You can enjoy playing a game of basketball on the court with the kids! If interested, inquire about our fishing and hunting at the Ranch! We hope you enjoy your country getaway!

Guest favourite
A well-maintained grassy area is bordered by a wooden fence, providing privacy. The foundation of the building is visible alongside a set of steps leading to the entrance. Bright blue skies and greenery enhance the peaceful surroundings.
Farm stay in Watonga
4.91 out of 5 average rating, 45 reviews

Bedford Ranch Airbnb

If you like dirt roads, farm animals, and fishing, this is just the place! We are close, & there is plenty of hospitality from our cats, chickens, cows, horses, and dogs. Not to worry, though. We have a privacy fence for your comfort where you can overlook and see the beauty of green grass and enjoy the fresh air. Take a peek out to the pasture, and see if the cattle are close by grazing. Most of all, being able to enjoy the countryside and the turning of windmills.

Guest favourite
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, 245 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 favourite
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, 53 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.

Popular amenities for Chester holiday rentals

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