Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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

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Top Guest favourite
Guest suite in Collierville
4.95 out of 5 average rating, 257 reviews

Collierville cottage on 3 acre farm

Spring is starting to bloom 🌸 Come enjoy our family farm located on 3 acres in the peaceful countryside of Collierville. We welcome guests in separate downstairs guest house with private entrance and porch overlooking pool. Look no further for a nature lovers retreat only minutes from city life. No trains or busy street noises just birds singing and crickets chirping. Amazing restaurants and shopping minutes away when you’re ready to explore! The pool is CLOSED until late May. Water is freezing

Top Guest favourite
Guesthouse in Somerville
5 out of 5 average rating, 18 reviews

Quiet Country Garage Apartment - Sleeps 2 Adults +

Small garage apartment on owner's property in quiet country setting. Sleeps 2 adults + 2 children on one queen bed and a futon (makes full-sized bed). Kitchenette: microwave, toaster oven, electric tea kettle w/ instant coffee pkgs, refrigerator. Pots/pans for cooking on outside grill top. WiFi; TV w/ local channels and ROKU. Enjoy sitting on outside deck. 7 mins. to Blue Oval Ford; 30 mins. west to Memphis Wolfchase; 20 mins. west to Arlington (TN); 45 mins. east to Jackson (TN)

Top Guest favourite
The exterior of a spacious brick home is featured, set against a lush green lawn. Large windows allow natural light to enhance the warm brick tones, while the surrounding trees provide a tranquil backdrop.
Home in Oakland
4.97 out of 5 average rating, 72 reviews

The Bartholomew: 3BR/2BA • King + Jacuzzi Tub

Welcome to The Bartholomew—your perfect retreat! This spacious 3-bedroom home with a study offers comfort, tranquility, and modern amenities. Enjoy a fully equipped kitchen with a coffee station, a master suite with Jacuzzi, and a patio with a grill for relaxing evenings. With WiFi, laundry, and self check-in via keyless entry, your stay is effortless. Located in a peaceful neighborhood, unwind, recharge, and create unforgettable memories in this cozy, serene home. “Your Cozy Retreat”

Top Guest favourite
The sun sets over a calm lake, casting warm orange and yellow tones across the sky. Silhouetted trees frame the view, enhancing the serene atmosphere. The reflection of the sunset can be seen on the water, creating a peaceful scene.
Home in Williston
5 out of 5 average rating, 21 reviews

The Cottage at Sunfire Farm

Newly remodeled countryside retreat with peaceful lake views, stunning sunrises and sunsets-the inspiration behind our name, Sunfire Farm. Enjoy fishing from the shore, watching wildlife, and stargazing under quiet country skies. Fully equipped kitchen and all the comforts of home. In the fall, pick your own pumpkin, carve it by the campfire and enjoy the harvest season. The quiet side of life is closer than you think-come unwind, slow down, and let us host your peaceful stay.

Top Guest favourite
A well-appointed kitchenette features a vintage refrigerator and wooden shelves displaying various kitchen items. A small round table and a single chair are positioned on a patterned rug, while natural light fills the space through large windows, creating a bright and airy atmosphere.
Guesthouse in Midtown
4.98 out of 5 average rating, 190 reviews

Birch Cottage: midtown charm & driveway parking

Peaceful guest house with central heat and air, close to everything and no cleaning list! Enjoy driveway parking and complimentary snacks in our comfortable space full of vintage furniture and books. Our historic neighborhood is located blocks from the highway, 7 minutes from downtown, 5 minutes from midtown's best restaurants and shops, & 12 minutes from Graceland and the airport. Explore Memphis and rest in our charming cottage! A full size second bed is available by request.

Guest favourite
A wooden sign reading 'SUNSET' is positioned above a gravel pathway leading to a welcoming country home, surrounded by trees. The inviting entrance opens to a lush green landscape with floral accents and unobstructed views of the fields beyond.
Home in Crawfordsville
4.94 out of 5 average rating, 216 reviews

Sunset Ittelegna

Take it easy at this unique and tranquil getaway. Secluded, country home with lush gardens and saltwater pool. Sunset Ittelegna is just 20 minutes from Memphis, TN. Fully functioning mini kitchen and separate living space. There is a private drive dedicated to the freestanding home.You’ll enjoy sweeping views of the Delta and most breathtaking sunsets through a wall of floor to ceiling windows.Sunset Ittelegna offers privacy and comfort. Perfect for your getaway.

Top Guest favourite
A modern kitchen is featured, with light-colored cabinetry and a spacious island at the center. Elegant pendant lights hang above, while stainless steel appliances and a coffee maker are visible. A window allows natural light to illuminate the area, complemented by decorative wall elements.
Home in Millington
4.99 out of 5 average rating, 121 reviews

The Cottage at Kerrville

A cozy 3 bedroom cottage in the historic community of Kerrville, Tennessee. Situated on 5 acres with plenty of room to roam. Newly renovated, fully furnished. Complete with kitchen, laundry room, and oversized shower with endless hot water. Beds are queen size with new memory foam mattresses and ceiling fans in each bedroom. Covered carport with well-lit exterior. Seven minutes from the Navel Air Station in Millington, and 25 minutes from Downtown Memphis.

Top Guest favourite
The tiny house features a rustic wooden exterior with a red metal roof. Soft ambient lights are strung around the door area, which is framed by greenery and flower beds. Outdoor seating is provided by two white chairs on a gravel patio, creating a welcoming space.
Tiny home in Olive Branch
4.98 out of 5 average rating, 149 reviews

The Pony

-Boasting a small hoofprint of 128 square feet with a loft. Ideally situated in a safe area for those visiting/passing through Memphis. -Tranquil views of open fields, horses, and a variety of other furry friends at a working horse boarding barn. -Stay solo or with someone you don't mind cozying up to. Ideal for mobile guests comfortable with stairs and tighter spaces. Locals or those without positive reviews will be rejected. Our property is non smoking.

Top Guest favourite
A cozy corner of the living room features a brown sofa adorned with decorative cushions. A small side table adds functionality. Natural light enters through the window, which is partially covered by blinds. A large mirrored frame reflects the inviting atmosphere.
Guest suite in Shelby County
4.86 out of 5 average rating, 417 reviews

Duplex attached to our house! Safe Memphis suburb!

Private outdoor entrance. There is no access from the main house to the duplex and vice versa. Private! No shared spaces, no hidden cleaning fees. This cozy duplex has a living room with kitchenette ( mini fridge, microwave) and a bathroom and is attached to our house. Sleeps 2 adults, and up to 2 small children. We don’t accept guests from Memphis and don’t feel our property is right for romantic getaways considering we live next door and have kids and dogs

Guest favourite
The exterior of a spacious log home is depicted, featuring a large wraparound porch supported by muted stone columns. The roof is gently sloped, and multiple windows elevate the design. Surrounding greenery offers a serene atmosphere, while a stone wall partially encloses the property.
Guest suite in Lakeland
4.95 out of 5 average rating, 241 reviews

Log Cabin with Covered Bridge

Our property isn't just a place to spend the night, its a destination. A place to relax. We have been blessed to call this beautiful farmstead home for over 30 years. Upon entering the property you will traverse along the winding drive, rolling hills, across the lake on the covered bridge, and up the hill to the log home. Be sure to look around for the many deer, geese, ducks, turkeys, and other wildlife that also call our farm home.

Guest favourite
The exterior of a green tiny house is highlighted, featuring a covered porch with a wooden railing. Two potted plants with yellow flowers are positioned near the entrance, which includes a doorbell and window. Natural surroundings provide a serene atmosphere.
Tiny home in Atoka
4.86 out of 5 average rating, 210 reviews

Cozy and Quiet

This cozy tiny house is located off hwy. 14 on the edge of Shelby County and Tipton County. This tiny home sleeps 2 in a queen bed and 1 on a futon. Downtown Memphis is 30 min away. Millington, Bartlett, Atoka, Stanton, Arlington, and Lakeland are 20 min away. This home is in the country surrounded by beautiful trees. There is a pond, old barn, a few barn cats and chickens roaming the property. The property is gated and very quiet.

Top Guest favourite
A spacious bedroom features a comfortable bed dressed in light linens, complemented by decorative pillows. Two bedside lamps provide soft lighting, while a large window allows natural light to enter. A dresser with multiple drawers and wall art adds to the room's inviting decor.
Home in Arlington
4.98 out of 5 average rating, 185 reviews

Arlington/65” HDTV/25 min to BLUE OVAL/garage

Enjoy a stylish experience at this conveniently-located zero-lot home in Arlington on the edge of Memphis right off of interstates I-40 and 385 (exit 25). Plenty of room for the entire family in this 1,900 sq ft home with king bed in primary, queen in room down, queen in loft, and queen in 4th bedroom. Large table to dine around, 65” TV in den, additional smart TVs in all bedrooms. Fiber high speed internet. 2 car garage.

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Fayette County
  5. Oakland