Holiday houses in Chester

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.

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!

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!

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*

Lazy B Ranch House

The Lazy B Ranch House is located 2.4 miles from Weatherford OK. The master bedroom has a king size bed with jacuzzi tub and walk in shower. The other two bedrooms have queen size beds. It has a large living room, dining area, and full kitchen. There is a computer / office area as well. Free wifi covers the entire house. The laundry room has a washer, dryer, iron and ironing board. Outside you will find a fenced in back yard as well as charcoal and gas grills.

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.

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.

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!!

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!