Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

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

0 of 0 items showing

1 of 3 pages

Superhost

The front entrance features a sturdy door with a small window, framed by two decorative pots filled with colorful flowers. The exterior showcases textured stone walls and a covered porch, with light fixtures mounted above for security and illumination.

Home in Fairview

4.74 out of 5 average rating, 35 reviews

Country Home/Lake House - Fairview & Seiling area

Check out this brand new remodel! It is the perfect country location to all of NW Oklahoma's best communities and attractions! Sleeping 7 comfortably, with all of the amenities from home, this is the perfect property for a one night get away or a month long stay! With all new appliances & fixtures you wont want to leave this charming country property!!! 5 min to Fairview 8 min to Canton Lake 15 min to Seiling 25 min to Okeene 35 min to Watonga 30 min to Waynoka 40 min to Woodward 40 min to Enid

Top guest favorite

An open room is seen through a wide entryway, featuring a modern sofa in warm orange tones. A stylish coffee table, adorned with decorative items, complements a cozy seating area, while plants add a touch of greenery near the windows.

Guesthouse in Clinton

4.99 out of 5 average rating, 113 reviews

Garden House Retreat

Welcome to our Garden House. We once converted our garage to outfit a coffee roaster and have since curated the space into a cozy apartment nestled between garden beds. What a fulfilling DIY project! Here you will find modern day comforts mixed with finishing touches from days of old. Enjoy our eclectic sensibility and settle in for simple delights. A bath before bed and great coffee in the morning are some of our best bits. Stay for the night or for a while. We hope you relax in our calm space.

Guest favorite

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, 34 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!

Guest favorite

The exterior of Hilltop House is depicted, showcasing a single-story farmhouse with a light-colored facade. The property features a gravel driveway, sparse landscaping, and an adjoining grassy area. A flagpole and antenna are visible, contributing to the rural setting.

Home in Fairview

5 out of 5 average rating, 10 reviews

Hilltop House

Nestled on the top of the highest point in Major County, Hilltop House is an all original farmhouse built in 1950 recently restored in 2023. Whether you’re riding the dunes, visiting family or enjoying the Oklahoma countryside, we hope you choose Hilltop House for your stay! Nearby attractions: 14 miles to the Little Sahara Sand Dunes 24 miles to Gloss Mountains State Park 24 miles to Canton Lake 98 miles to Oklahoma City, OK. We are located 4 miles south of Hwy 412 off of Hwy 281.

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, 147 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.

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, 62 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, 40 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

4.87 out of 5 average rating, 129 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

4.92 out of 5 average rating, 215 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*

Top guest favorite

The charming exterior of a remodeled historical cottage is seen, featuring a wooden facade and a welcoming front porch. Flower pots enhance the entryway, and a grassy lawn extends outward. Large trees provide shade, while a carport is visible on the side of the cottage.

Cottage in Clinton

4.96 out of 5 average rating, 209 reviews

Historical Cottage on Route 66

Relax with the whole family at this peaceful place to stay. Beautiful remodeled historical cottage. 2 bedroom with King size bed in each room and 2 bath located on Route 66. Each bedroom has a Smart TV and there is a Smart TV in the main living area. An 18 hole golf course is located adjacent to the cottage. Private garage or barn to accommodate your vehicles. Come and breath the fresh air and enjoy your stay. 1 mile from downtown Clinton, Oklahoma.

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

4.92 out of 5 average rating, 39 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.

Top guest favorite

A spacious outdoor area showcases a large pool surrounded by a concrete patio. Comfortable seating arrangements are visible, including loungers and sofas. The home features multiple entry points, and string lights are draped overhead, enhancing the ambiance.

Guesthouse in Hinton

4.97 out of 5 average rating, 190 reviews

Hidden Treasure Pool House Near I-40

If you like a little extra in your travels, you're welcome to our 1300 sq. ft. Guest Home on a 17 acre setting just 35 minutes from downtown OKC or 20 minutes from Weatherford OK. Secure location with a gated entry and some quiet scenic country but just a short drive away from the action in OKC. Great place for couples, solo adventurers, business travelers, and a family with children. No parties or large groups. No more than 6 people on the premises.