Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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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, 71 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, 74 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, 29 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
Guesthouse in Somerville
5 out of 5 average rating, 27 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, k-cup coffee, 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
Guest suite in Collierville
4.95 out of 5 average rating, 265 reviews

Collierville cottage on 3 acre farm with pool

Summer has arrived 💦 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 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
4.98 out of 5 average rating, 127 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 Shelby County
4.86 out of 5 average rating, 437 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) bedroom, 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

Superhost
The exterior of the home is presented, featuring a welcoming entrance with a star motif. Two chairs are situated on the porch, and greenery surrounds the area, creating a comfortable environment for guests and pets. Natural light filters through the windows, enhancing the inviting facade.
Home in Holly Springs
4.83 out of 5 average rating, 231 reviews

Gallop-Inn Bungalow

PETS are welcome but please no more than 2 pets. Super easy self check in with keypad. Great location just outside the city and just a short drive to Historic Downtown Collierville, TN or how about a 30 minute drive to Downtown Memphis/Beale Street, Tunica Casinos, and Graceland. Plenty of Acreage for your pets to exercise. Enjoy the local sights of the area like Pickwick Lake and State Park less than an hour drive. Enjoy all the conveniences of home.

Top Guest favourite
Home in Stanton
5 out of 5 average rating, 25 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.

Top 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
4.96 out of 5 average rating, 247 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.

Top 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
4.87 out of 5 average rating, 224 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.

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, 194 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