Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
An aerial view captures the farmhouse nestled amid expansive green fields and trees. The property features a red-roofed house with outdoor spaces, horse grazing areas, and clear skies above, illustrating a serene countryside setting.
Farm stay in Arlington
5 out of 5 average rating, 81 reviews

FarmCharm getaway outside Memphis | Nearby winery

Experience the peaceful countryside of Arlington/Lakeland, just outside of Memphis, TN, with our charming family-friendly farmhouse retreat. Just a short drive from the big city (and just 15 min to the closest town), our comfortable home offers the perfect blend of relaxation and convenience. Featuring a fully equipped kitchen, outdoor seating, fishing pond access, BBQ grill, fire pit, and delightful interactions with our horses. Unwind on the front porch and enjoy the tranquil surroundings.

Top Guest favourite
A wooden dock extends into a serene pond, where a gentle fountain creates ripples on the water's surface. Soft lighting highlights the surrounding lush grass and trees under a fading sunset, contributing to a peaceful outdoor ambiance.
Guesthouse in Covington
5 out of 5 average rating, 66 reviews

Peaceful, Private Studio 1Bath

Relax and unwind with the sounds of nature without the hustle and bustle of the city noise around you. You will be able to enjoy the peaceful surrounding like the beautiful pond, and 8 acres of land that would be great for running, walking or just enjoying a picnic. Enjoy summer nights under the covered patio while you cool off from a full day of adventures. Located 30 minutes from Blue Oval City and about 50 minutes from Downtown Memphis. Unpack, unwind and find Serenity. **5g Wifi**

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, 73 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
Guest suite in Collierville
4.95 out of 5 average rating, 261 reviews

Collierville cottage on 3 acre farm

Spring is in full 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 officially open.

Top Guest favourite
A modern kitchen is highlighted, featuring a sleek island with three high-backed stools. Light fixtures hang above the island, and stainless steel appliances are present. Neutral tones are complemented by textured backsplash tiles, while natural light fills the space through a nearby window.
Home in Millington
4.98 out of 5 average rating, 124 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
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 Cordova
4.86 out of 5 average rating, 429 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

Top Guest favourite
Home in Stanton
5 out of 5 average rating, 20 reviews

Hillcrest Cottage

Make yourself at home at Hillcrest Cottage. Perfect for small families, short term work contracts, or business. **discount available for long term rentals** The home is located in a peaceful and beautiful community. Less than 5 minutes from Blue Oval City and I-40. The home is a 2 bedroom 1 bathroom with separate laundry room, spacious kitchen, formal dining room, and living room. There is an attached carport at the back door and a cozy front porch.

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, 243 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, 213 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
4.97 out of 5 average rating, 190 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.

Guest favourite
Home in Mason
5 out of 5 average rating, 13 reviews

Blue Oval City-Workers welcome! Wifi/truck parking

Relax with the whole family at Beaver Creek Farms, just minutes from Blue Oval City with easy access to Hwy 70 and I-40. This peaceful 4-bedroom, 3-bath home sleeps 8 and rests among rolling pastures, backing up to quiet woods for added privacy. Enjoy your morning coffee or unwind after a long day on the front or rear deck while watching deer and wildlife in the serene beauty of the Tennessee countryside.

Top Guest favourite
The front exterior of the cottage is depicted, showcasing a modern design with white vertical siding and a contrasting dark roof. A welcoming entrance is framed by a wooden overhang, with two symmetrical windows on either side. A garden bed with colorful flowers is visible near the pathway.
Guesthouse in Cordova
4.96 out of 5 average rating, 272 reviews

Cozy Cottage 1-BR Private Screened Porch

This one bedroom private cottage is tucked back in a little oasis we created for our family and guests. While enjoying morning coffee you will find space that insists you relax on the large screened-in porch and watch deer and other wildlife travel through the yard. Whether you are here to relax or work, there is no place better to do so than at your own oasis. We'd love for you to be our guest!

Popular amenities for Oakland holiday rentals

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