Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Top guest favourite
A spacious bed is centered against a wooden headboard, with light bedding and decorative pillows. Soft lamps flank the bed on each side, and a wooden tray holds a drink and floral arrangement at the foot. Natural light streams through windows with blinds.
Farm stay in Arlington
5 out of 5 average rating, 23 reviews

1B1B FarmCharm getaway | Near to Memphis & winery

Experience the peaceful countryside of Arlington/Lakeland TN, with a stay at our charming farmhouse retreat. This is our smaller-sized accommodations, perfect for couples, budget-conscious travelers and small groups. Just a short drive to Memphis, TN (& 15min to the closest town), our comfortable home offers a 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.

Guest favourite
The kitchen features blue cabinetry, equipped with glass-fronted upper cabinets displaying dishware. A white refrigerator sits beside a wooden cart with an oven and fruits. Natural light filters through a window above the sink, enhancing the bright, inviting space.
Guest suite in Rhodes View
4.96 out of 5 average rating, 130 reviews

Rhodes Midtown Haven | The Hallwood Loft

Welcome to our luxurious upstairs suite, a stone's throw from Rhodes College. Nestled in a gated property with secure parking, this comfy haven boasts a separate entrance for your privacy. Relax on the rooftop patio, or unwind indoors with our massive 85" 4K TV. The suite features a king-sized bed for supreme comfort, a well-stocked kitchen, and a dedicated workspace with fast WIFI. Perfect for work travel or visiting parents, our space offers a blend of luxury, security, and prime location.

Guest favourite
The exterior of the cottage is framed with natural wood and features a screened porch, allowing for views of the surrounding forest. A wooden staircase leads to the entrance, and a stone pathway guides visitors through the lush, green landscape.
Cottage in Coldwater
4.95 out of 5 average rating, 176 reviews

Wynnewood - Odell Cottage

Country get-away! Only 30 Minutes from Downtown Memphis, TN, yet out in the country on a 62 acre estate. Nature trails through the property allow for beautiful, peaceful strolls. We have fishing (in season). **** This cottage is set back in the woods and there is not a TV in this unit but there is Wifi. We have created a serene and unplugged experience. We have the "Wynnewood Elizabeth Cottage" and the "Wynnewood Jettie Jewel cottage" on our property that are listed separately.

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, 71 reviews

"The Bartholomew” 3 Bed 2 Bath King w/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 cozy living room area is showcased, featuring a dark sofa and a light-colored coffee table. Accent pillows add warmth to the seating options. A lamp and two candles create a soft glow, while a wall-mounted mirror enhances the space's depth.
Guest house in Cordova
4.92 out of 5 average rating, 261 reviews

BE OUR GUEST: Adorable Guest House in EastMemphis

Perfect for passing through Memphis. Located in a beautiful neighborhood near 140. Weather you’re touring Memphis for the weekend or in for rotations at work, we have your home away from home waiting for you. Those who love being out doors will enjoy the wooded yard with a sitting area around the fire-pit. There is also a Sofa-sleeper (queen bed) for additional guest. Very centrally located and near I-40 allowing you to be most anywhere you need to be in 20 minutes.

Top guest favourite
Guest suite in Collierville
4.95 out of 5 average rating, 244 reviews

Collierville cottage on 3 acre farm

Fall is here 🍁 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 due to cold temps.

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, 128 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 Cordova
4.85 out of 5 average rating, 399 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
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, 232 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
4.85 out of 5 average rating, 184 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
4.98 out of 5 average rating, 169 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.

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.
Guest house in Cordova
4.95 out of 5 average rating, 253 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