Holiday rentals 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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Guest favourite
A rustic cabin is shown with a green metal roof and wooden façade, complemented by a wraparound porch featuring a set of stairs. Gravel surrounds the cabin, and two large trees provide shade in the foreground.
Home in Oakland
4.92 out of 5 average rating, 116 reviews

Hidden Treasure at Enid Lake

This peaceful location will have you relaxing and unwinding in no time. This is a true rustic cabin experience approximately 1 mile from George Cossar State Park. This is great for hunting, fishing or just relaxing with family. The park offers a playground, a putt putt golf course, and a disc golf course. The cabin has 3 bedrooms, living room, kitchen and 1.5 baths. The exterior has a 3-sided wrap around porch, 30x40 enclosed garage, and fish cleaning station. Parties & events are not allowed

Guest favourite
The exterior of the home is highlighted by a well-maintained brick facade and a welcoming porch, framed by lush greenery. Two front-facing windows allow natural light to illuminate the interior, while the surrounding lawn offers ample space for outdoor activities.
Home in Pope
5 out of 5 average rating, 12 reviews

Near Enid Lake & Ole Miss

Newly updated 3 BR 2.5 BA home w/ all new beds/bedding, updated furniture/amenities for a comfortable stay. Included: AC/heat, WiFi, wash/dryer, iron and board. Carport for parking along with room for boat/trailer parking. You'll feel at home while you're traveling in north Mississippi. Great location just off I-55 & within an hour of the Memphis International Airport. Close to Enid, Sardis and Grenada Lakes for the fisherman/outdoors fans. Sports fans only have a 35+- minute drive to Ole Miss.

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, 16 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, 425 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
A spacious great room features two light-colored leather sofas and a wooden coffee table positioned on a textured area rug. Warm wood accents are complemented by a large ceiling fan and natural light from the windows. A dining table is visible in the background.
Cabin in Pope
4.9 out of 5 average rating, 80 reviews

Cheerful & Modern 3 bedroom Cabin with Fire Pit

Have fun with the whole family at this stylish place. Nestled amongst the trees, and just a short walk to Enid Lake, Enjoy your peaceful stay in this quiet modern cabin. Have fun fishing in the ponds, float out on the lake, or roast some smores in the fire pit in the backyard. A great location to escape the hustle and bustle of the city, or take a short day trip to Jackson or Memphis. Ole Miss is a 38 minute drive away.

Top guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows. Two accent chairs flank a glass coffee table, which holds magazines. Soft lighting is provided by two lamps, while a large artwork of a bull head serves as a focal point above the sofa.
Apartment in Oxford
4.94 out of 5 average rating, 376 reviews

Contemporary, The Oxford Retreat, Walk to Games!

The Oxford Retreat – Your Hub for Ole Miss Excitement! Stay in the heart of the action, walking distance to Ole Miss Stadium, Swayze Field, and The Grove. The Oxford Retreat offers modern contemporary décor with mid-century accents. Serene, neutral colors and comfort are at the forefront. Vaught-Hemingway Stadium – 0.9 miles Swayze Field – 0.9 miles Oxford Square – 1.8 miles The perfect spot for game day and relaxation!

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, 16 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
The historic house is depicted in soft evening light, showcasing an inviting front porch with a swing and decorative columns. Lush greenery and well-maintained flower beds frame the front yard, while the surrounding neighborhood is visible in the background.
Home in Water Valley
4.99 out of 5 average rating, 103 reviews

The Cedars 1863 Guesthouse

My place is close to Downtown, walking distance to the shops, banks, coffeehouses and restaurants. You’ll love my place because it was built in 1863. Whether you are relaxing on the front porch swing, eating a snack on the veranda or maybe just meditating on the back porch, my place offers a quiet place to unwind. My place is good for couples, solo adventurers, and business travelers.

Top guest favourite
A spacious home is surrounded by greenery, featuring a screened-in porch along the front. The building's design includes large windows that invite natural light. A gravel driveway leads to the entrance, enhancing the welcoming appearance of the property.
Home in Sardis
4.93 out of 5 average rating, 153 reviews

Cabin on the water at the lower lake of Sardis

Wonderful home located on the water at the lower lake of Sardis. There is a private dock and a boat ramp only 1 house over. Located 3 mins from the upper lake & the marina. Screened in front & back porch. Firepit in backyard. Great getaway spot! OWNERS HAVE NO ADVANCE KNOWLEDGE OF WATER LEVELS ON THE LOWER LAKE OR IF THE DOCK WILL BE ACCESSIBLE.

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, 40 reviews

Cuckoos Nest

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