Holiday houses in Hennessey

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Top-rated holiday rentals in Hennessey

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Top Guest favourite
A spacious bedroom features a four-poster bed with soft blue and white bedding. A dark, tufted bench sits at the foot of the bed, and a bedside table with a lamp is positioned next to a window that allows natural light to enter the room.
Apartment in Edmond
4.95 out of 5 average rating, 40 reviews

1-Br Private Apt. in Gated Community

Enjoy a relaxing stay in our newly renovated unit in Edmond's Antler Farms neighborhood. Just minutes from Quail Springs Mall, dining, and shopping, you're also close to Lake Hefner (8.8 miles), Rose Creek Golf Course (2.6 mi), Downtown OKC (18 miles), and Downtown Edmond (7 miles). Experience the perfect blend of luxury, relaxation and convenience, with easy access to city amenities and local attractions. Ideal for both relaxation and exploration. Unit comprises entire wing of an existing home.

Guest favourite
A welcoming living area features two comfortable leather chairs positioned around a small table. Tall windows with decorative curtains allow natural light to fill the space, while a potted plant adds a touch of greenery. A patterned rug lies beneath, complementing the warm wood flooring.
Home in Kingfisher
4.86 out of 5 average rating, 59 reviews

Kade's Casita

Welcome to Kade's Casita where we invite you and your family to come visit this unique 100 year old home in the heart of Kingfisher. You are greeted by a spacious living room that opens to the formal dining room followed by the kitchen. You will stay in one of three bedrooms outfitted with queen and twin beds. Feel free to take advantage of the washer and dryer as well as enjoy your morning coffee in the sun room. Spacious 2 car attached garage is available with every stay! Come enjoy your stay!

Top Guest favourite
The exterior of a quaint red schoolhouse is viewed at dusk, illuminated by soft pathway lights. A bell tower rests atop the building, while windows reflect a warm glow. Surrounding grass and a fenced area create a welcoming outdoor space.
Guesthouse in Edmond
5 out of 5 average rating, 76 reviews

Red Rooster Retreat - Edmond/Guthrie

Entire 400 sq ft Guesthouse to yourself. This historic-looking schoolhouse was used by two families for homeschooling. It has recently been transformed into a cozy farmhouse cabin for dreamy overnight getaways. Nestled perfectly close to Edmond, Guthrie, and the Lazy E Arena, you're just a hop, skip, and a jump away from concerts, rodeos, and top-notch dining adventures! Ring the schoolhouse bell, enjoy farm animals, and make some memories at this unique and family-friendly place! Enjoy!

Top Guest favourite
A light-filled living area features a wooden loveseat with cushioned seating and a rustic wooden coffee table. A wall-mounted TV is visible above a leather rocker. Large windows frame views of the garden, while subtle brick accents add warmth to the space.
Guest suite in Edmond
4.96 out of 5 average rating, 421 reviews

Hidden Hollow Honey Farm: firepit, wildlife, fun!

Low single occupancy rate, $10/guest thereafter. Tucked away on 5 serene acres in central Edmond, Hidden Hollow Honey Farm offers 540sq ft of safe, quiet lodging w/in walking distance of Edmond restaurants & activities. Close to Mitch Park/Golf/Route 66/OCU & UCO/Soccer/Tennis. 2nd bedroom is a small bunkhouse for kids - see pics. WIFI, 2 big Smart TV’s w/antennas, King bed, toys/books/games, rustic cottage kitchen w/coffees/teas/snacks, patios w/firepits/swings, pond/apiary views, & wildlife.

Top Guest favourite
An inviting open-concept kitchen and dining area displays a rustic wooden dining table surrounded by clear acrylic chairs. A modern chandelier hangs above, complemented by stainless steel appliances and textured glass backsplash. Natural light enters through large windows, adding warmth to the space.
Cabin in Arcadia
4.98 out of 5 average rating, 150 reviews

Farmhouse Retreat

Need a break from the busyness? Just driving through? Coming in to town to see family or friends? Want a weekend getaway? Come stay in a relaxing and well furnished farmhouse located on 40 acres in the hills of Arcadia, OK. The property features over a mile of wooded walking trails, a three acre pond, family friendly farm animals including everyone's favorite, Kenny the Clydesdale, a scenic back porch and more. The property and farmhouse is family friendly and accommodates up to six guests.

Guest favourite
The living area features exposed brick walls and hardwood flooring. A comfortable gray couch and a recliner chair are arranged around a low coffee table, with a wall-mounted television positioned above. Natural light filters through window blinds, creating a relaxed atmosphere.
Apartment in Enid
5 out of 5 average rating, 7 reviews

100 Grand

Located downtown, this renovated building offers a unique space close to all the things that make up Enid. Nightlife, restaurants, David Allen Ballpark and the Stride Center are all nearby and walkable. Built in 1927, This two story building is rumored to have been a one stop shop back in its glory days. With poker and liquor on the ground level and a brothel upstairs, this place has always been hopping! While it’s much more tame today, we still think you’ll feel like a hundred grand here!

Guest favourite
A modern living area features a spacious sectional sofa with accent pillows, complemented by two stylish armchairs. A round coffee table is situated in the center, and a flat-screen TV is mounted above a brick fireplace. Natural light enters through large windows, enhanced by soft window treatments.
Home in Enid
4.93 out of 5 average rating, 111 reviews

Spacious 3Bed/2bath -long stay discounts avail

This relaxing, modern 3 bed and 2 bath farmhouse sanctuary is a Perfect location to energize or relax while enjoying the Enid Community. From our welcoming family room/kitchen lounge area to your spacious walk in closet bedrooms. Every inch of this quiet escape is surrounded by a family friendly neighborhood, and fenced backyard with a Personal Concierge and Host, dedicated to assuring your experience is comfortable and relaxing or energizing and active depending on your taste and desire!

Top Guest favourite
A spacious living area is characterized by a light-colored fireplace and a decorative clock on the wall. Comfortable seating is arranged around a coffee table, complemented by a colorful area rug. A dining table is visible in the background, leading to a well-equipped kitchen.
Bungalow in Guthrie
4.95 out of 5 average rating, 224 reviews

Clean and Cozy Craftsman Style Bungalow

This bungalow is blocks from downtown Guthrie, where guests can enjoy shops, the Pollard Theater, and restaurants. It has new furnishings, including amenities such as a washer-dryer, high-speed Wi-Fi, cooking necessities, a large backyard, and parking on the premises. It has a great front porch area with a swing and seating where guests can relax and enjoy the small-town nostalgia of Guthrie. Guests enjoy the character of our historic home with all the modern amenities.

Top Guest favourite
A spacious den features a large sectional sofa adorned with decorative cushions, positioned next to a coffee table. Natural light filters through sheer curtains, creating a bright atmosphere. Artwork and lamps add a touch of character to the inviting space.
Home in Enid
4.98 out of 5 average rating, 98 reviews

Best Enid Neighborhood - Darling 1939 Gem!

Enjoy a peaceful experience at this centrally-located home in the best neighborhood in Enid. The Davis House is a 3 bedroom 1 bath house, built in 1939, full of character, recently renovated and decorated in a minimalist, modern way. Close to Vance Air Force Base, the walking trail, Champlin Park, downtown, both hospitals, shopping and restaurants. This is a low-tox home that is perfect for those who are health conscious or sensitive to harsh cleaners & products.

Top Guest favourite
A modern living area features a gray sofa adorned with decorative cushions. A light fixture hangs from the ceiling. The coffee table is centered on a patterned rug, while a television sits on a cabinet across from a fireplace. A doorway leads to the bedroom.
Home in Helm Farm
4.95 out of 5 average rating, 470 reviews

〰️The Nomad | Walk to Western Ave District

Stylish 100 year old duplex that’s been remodeled with a mid century modern design. 2 minute walk to the best restaurants, bars and coffee shops in the Western Ave District. Keeping with the original semi studio floor plan, the residence has 1 bedroom with a queen bed and the living room has a queen sized sofa bed. **Memory foam mattresses on both beds** Equipped with brand new appliances including a washer/dryer and all the kitchen necessities you’ll need.

Guest favourite
Place to stay in Stillwater
4.83 out of 5 average rating, 582 reviews

Cozy 2BR Private Farmhouse/Full bath/kit/Patio

Welcome to our Cozy Farmhouse on Main St. centrally located less than a mile from Boone Pickens Stadium. Enjoy Free Parking on Game Day and the Cozy Warmth of a 2 bedroom Farmhouse feel with a Large Outdoor Patio. Enjoy Tailgating with family and friends on game day with on our Large Patio, Grill, and Fire Pit. Also included on our Patio, is a Large 40,000 BTU Propane Gas Fire Pit to keep you warm on the cool Fall Football Games.

Top Guest favourite
A comfortable living area features a plush sofa and two modern chairs arranged around a circular coffee table. A textured area rug defines the space, while large windows allow natural light to fill the room. A fireplace adds a cozy focal point, complemented by a decorative plant.
Home in Enid
4.97 out of 5 average rating, 117 reviews

The Blissful Bungalow

Old world charm with all the luxury amenities you've been looking for. A chef's kitchen with high end gas range and oven with air fry capabilities. With an instant hot water tank you'll never run out of hot water. Three generous bedrooms- king, full, and twin trundle beds. High end furnishings and beautiful touches throughout, you'll love your stay at the Blissful Bungalow!

Popular amenities for Hennessey holiday rentals