Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Top guest favourite
The exterior of the cabin features a metal roof and light-colored siding, flanked by large windows. A welcoming entrance with double wooden doors is flanked by potted plants. A small seating area with two chairs and a table is positioned on the porch, surrounded by gravel landscaping.
Cabin in Sardis
4.95 out of 5 average rating, 19 reviews

Newly Renovated Cabin- Sardis Lake- Cabin #1

Welcome to your perfect Sardis/Oxford-area getaway! This beautifully renovated cabin offers the charm of country living with all the modern comforts. Nestled just mins. from Sardis Lake, and a short drive to Ole Miss and Oxford’s iconic Square, this is the ideal retreat for outdoor lovers, football fans, and anyone looking to unwind in a peaceful, central location. Whether you’re in town for a game, a weekend of lake adventures, or just looking to relax, this cabin is your home base for it all.

Guest favourite
A cozy living area is presented with a light-colored sofa and a floor lamp, enhancing the space’s warmth. Large windows provide views of the surrounding greenery, while a wooden door leads to a deck. Exposed beams and log walls contribute to a rustic atmosphere.
Cabin in Pope
4.83 out of 5 average rating, 88 reviews

Cabin w/Pond, Fire Pit, Boat Ramp & Hunting Access

Perfect location for your next lake adventure! Nestled in Plum Point, a peaceful neighborhood at Enid Lake, with a boat ramp just around the corner and trails leading to a sandy beach you can access on foot. Enjoy coffee on the deck overlooking the 3-acre private pond. The property features a fire pit with Adirondack seating and is directly connected to Corps of Engineers land-offering access to hundreds of acres to hunt. A true hunter’s paradise, whether you’re fishing, paddling, or unwinding.

Guest favourite
An inviting living area is presented, featuring a comfortable gray sofa facing a white brick fireplace beneath a wall-mounted television. Shelves on either side of the fireplace display decorative items. A natural fiber rug covers the floor, complementing the wood-style flooring.
Home in Pope
4.97 out of 5 average rating, 32 reviews

Newly Renovated Near Enid Lake

Relax with the family in this cozy country house or bring your fishing buddies and enjoy nearby lakes with plenty of room to park a boat! This newly renovated house features an open floor plan with three bedrooms and two full bathrooms. Plenty of room to comfortably sleep 6-8 people. Located a mile from I-55, this property is an easy 30 minute drive to Oxford and an hour to Memphis. For visiting fishermen, it is only a few mins from Enid Dam, 20 mins from Sardis Dam, & 30 mins from Grenada Dam!

Guest favourite
A welcoming living area features two striped armchairs, a wooden side table, and a comfortable sofa. A large TV is positioned on a wooden stand, while natural light enters through a window. A barn-style door leads to another room, enhancing the cozy atmosphere.
Home in Pope
5 out of 5 average rating, 17 reviews

“The Spinney” at Enid Lake

Your cozy getaway awaits on Enid Lake at “The Spinney”. Just steps away from Wallace Creek Campground, approx. 0.5 miles to McCurdy Point boat ramp and 1 mile from I-55, The Spinney has the amenities and location to be a fisherman’s dream! With 3 full beds in 2 bedrooms, as well as a sofa bed, this cozy property offers a comfortable stay for guests. Whether your visit entails water experiences on the lake or exploring amenities in the area, we hope you enjoy what The Spinney has to offer.

Top guest favourite
A cozy bedroom features a four-poster bed with a white comforter and decorative pillows. Natural light enters through a nearby window adorned with light curtains. A mirrored accent and bedside lamps contribute to the inviting ambiance, while a stylish cowhide rug adds warmth to the wooden floor.
Farm stay in Oxford
4.99 out of 5 average rating, 430 reviews

The Cottage, 2BR Farm Stay by Velvet Ditch Villas

Escape to The Cottage, a charming farmhouse getaway just 8 miles from Oxford. Set on 4 peaceful acres, this cozy retreat blends vintage and shabby chic décor for a warm, inviting vibe. Start your day with fresh eggs, meet our friendly farm animals, and enjoy evenings by the fire pit under stunning starry skies. Perfect for a romantic escape or quiet retreat, The Cottage offers countryside serenity with easy access to Oxford’s dining, shopping, and entertainment. Book your stay today!!!

Superhost
An open living area features a high wooden ceiling with exposed beams and a stone fireplace. Comfortable seating is provided by brown leather sofas and a cozy armchair. A coffee table sits in the center, with a decorative plant and a dog bed nearby. Natural light shines through large windows.
Cabin in Oakland
4.77 out of 5 average rating, 13 reviews

The Presidential Lodge

Make this your very own happy place. The Presidential Lodge is fully furnished, nestled in a rustic area, surrounded by Cossar State Park and the Corp of Engineers recreational area, only 1.2 miles from Enid Lake & Cossar boat ramp. Perfect location for Ole Miss sports, fishing trips, "Gramping" (grandparents and grandkids), family vacations, family reunions and wedding celebrations. Pack for a night, a weekend escape or a fun-filled week away. Come enjoy our little piece of heaven.

Top guest favourite
A spacious studio apartment features a queen-sized bed with a blue and white patterned quilt, complemented by decorative pillows. A dual recliner loveseat and writing desk are included. Tall windows allow natural light to fill the room, while a private entrance is visible in the background.
Guest suite in Oxford
4.92 out of 5 average rating, 265 reviews

Spacious Oxford Retreat - Large Yard

Spacious studio apartment with 10 ft ceilings and tall windows make it bright and airy. Located in a quiet, wooded neighborhood just a 10 minute drive from campus or the Square. Queen-sized bed, dual recliner loveseat, writing desk, bar top dining table, washer/dryer unit, and kitchen with full size refrigerator, microwave, and stovetop. Private outdoor patio that is fenced-in. Personalized door lock code for added security. Roku TV and free WiFi.

Top guest favourite
A bright living area is presented, featuring a large flat-screen television mounted on the wall and a comfortable white sofa. A coffee table and stylish side tables complement the space, while ceiling fans add ventilation. French doors lead to a balcony that offers views of greenery.
Apartment in Oxford
4.93 out of 5 average rating, 120 reviews

A New Luxury Oxford Condo Close to Everything!

Newly Renovated Building in Oxford’s HOT Rowandale Village! Experience the best of Oxford in this newly renovated building, ideally located in the vibrant Rowandale Village. Enjoy fantastic amenities like pools, pickleball courts, volleyball, and more! Best of all, you're just minutes away from the Square and Ole Miss Campus, putting you in the heart of all the action. This property is located on the third floor and does not have elevator access.

Guest favourite
Tiny home in Enid
4.91 out of 5 average rating, 32 reviews

Jason and Vicki's Love Shack

This unique place has a style all its own. Filled with local art. The Love Shack is located in beautiful Tallahatchie County, and about an hour from Memphis. Only a half hour drive to Oxford and Ole Miss. Overlooks our 40 acre property and 3 acre pond. It has is own private entrance and parking area. Like the song from the B52's--- Well it's set way back in the middle of a field, Just a funky old shack and I gotta get back.

Guest favourite
The exterior of a single-story home is shown, featuring a metal roof and a front porch with seating. Nearby, a satellite dish is mounted. The home is surrounded by trees and a gravel driveway leads up to it, emphasizing its peaceful rural setting.
Home in Yalobusha County
4.88 out of 5 average rating, 17 reviews

Coffeeville getaway minutes from Grenada lake

Looking for a little getaway not far from some outdoor adventure? This is for you! Minutes from Grenada lake; and only 30 minutes from Oxford/Ole Miss. Three bedrooms and two bathrooms. fenced inlet friendly backyard. Covered parking. Great for a weekend getaway to head to the lake for some fishing and sight seeing. Gas heat, stove, and grill. Great back porch for grillin and chillin. Recently remodeled.

Top guest favourite
A cozy sleeping area features a queen bed with white linens and decorative pillows. Colorful artwork adorns the walls, while a dark patterned area rug covers the floor. A plush chaise lounge provides additional seating, complemented by two bedside lamps for soft lighting.
Farm stay in Oxford
4.98 out of 5 average rating, 408 reviews

Art Gallery Apartment

This basement apartment is below Oxford Treehouse Gallery in beautiful Lafayette County. It is nestled in the trees down a private drive only 6.5 miles from the Oxford Square. It has a private entrance with an outside covered seating area and access to the screened porch off the gallery.

Top guest favourite
A spacious living area features a sectional sofa with decorative pillows and a plush chair, oriented towards a coffee table. Natural light enters through large windows, adorned with sheer curtains. A dining area is visible in the background, accommodating a round table with seating for four.
Home in Courtland
5 out of 5 average rating, 45 reviews

Cuckoos Nest

Traveling nurses and out of town construction workers are welcomed. Enjoy a stylish experience at this centrally-located place. A 45 minute to an hour drive to Memphis, Tennessee, and 25 minutes from Oxford, Mississippi. this home is not only beautiful, but very relaxing.

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Mississippi
  4. Yalobusha County
  5. Oakland