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
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
A spacious sleeping area features a queen bed with decorative pillows. A small table stands at the foot of the bed. Framed artworks adorn the walls, and light enters through windows with soft curtains, contributing to a serene environment.
Guesthouse in Midtown
4.98 out of 5 average rating, 228 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.

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, 438 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

Top Guest favourite
Tiny home in Olive Branch
4.98 out of 5 average rating, 171 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
Home in Stanton
5 out of 5 average rating, 26 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.

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