Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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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, 14 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
A curved driveway leads to a modern home surrounded by lush greenery. Large windows reflect the blue sky, and several trees provide shade, creating a pleasant entrance. The architecture features a single-story design with a welcoming atmosphere, set against an expansive outdoor landscape.
Farm stay in Coffeeville
4.97 out of 5 average rating, 39 reviews

Remodeled Mid-Century Farm House Close to Oxford

Come experience a peaceful get-a-way at the farm. This newly remodeled home sits on 18 acres over-looking a row crop and cattle farm. While it is in the peaceful country, it is also only 30 minutes from Oxford, MS, 30 minutes to Grenada Lake, and 30 minutes to Enid lake. So whether you are looking for a quiet, family retreat, a game day house to share with friends, an easy drive to Grenada lake for a fishing weekend, or a fun filled summer weekend at Enid Lake; this is the perfect home for you.

Superhost
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, 94 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
4.95 out of 5 average rating, 38 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!

Top guest favourite
A spacious dining area features a round table surrounded by wooden chairs, complemented by a decorative area rug. Large windows invite natural light and provide views of the outdoors, while a chandelier hangs gracefully overhead, enhancing the room's charming design.
Barn in Oxford
4.96 out of 5 average rating, 144 reviews

Unique Barndominium Private Retreat Experience

*Converted barn, incredible accommodations, more than just another place to stay. *10 minutes to Square & Campus *KING en suite *2nd FULL BR *Wi-Fi *Parking *Furnished kitchen w/ice machine *Coffee/tea bar *Movie theater w/projector & screen (seasonal use) *POOL-across the driveway *Lg back porch with picnic table *Patio with fire pit & grill *Indoor/outdoor Bar *Peaceful view of meadow, mixed woods forest *Gazebo *Unique experience *Dogwash station BOOK your getaway now or WISHLIST us.

Guest favourite
A ranch-style home is seen with a covered porch featuring comfortable seating arrangements. Large windows allow natural light to brighten the interior. The surrounding greenery adds a peaceful touch, while the roof is lined with trees, creating a serene outdoor atmosphere.
Home in Water Valley
5 out of 5 average rating, 13 reviews

Cowboy’s Rebel Ranch

Relax with the whole family at this peaceful ranch style home, an ideal retreat in Mississippi! This delightful 3-bedroom home is conveniently located just 2 minutes from a boat landing for fishing or water-sports. It’s only 18 miles from the vibrant campus of Ole Miss University. Perfect for catching a game or enjoying the local dining and shopping options in the charming town of Oxford, known for its vibrant culture and southern hospitality. This home is the perfect space for your stay.

Guest favourite
The exterior of the remodeled farmhouse is shown at night, featuring a spacious front porch with two red chairs. Softly illuminated by lights, the door and windows provide a warm and inviting entryway. A pathway leads up to the porch, surrounded by grassy areas.
Cottage in Grenada
4.82 out of 5 average rating, 125 reviews

Ms Maggie's Place

Miss Maggie's Place is a true country farmhouse that has been remodeled with a modern amenities. The house was built originally as a double shotgun farmhouse. It was originally located on Grenada Lake, for engineers that built the lake. Relax with the whole family at this peaceful place to stay. House is located on 3 acres, in the city limits. Close to shopping areas highways and interstate 55. Large front porch and back porch. Enjoy watching the deer & remodeled large bathroom.

Guest favourite
A single-story cabin is presented with a neutral-colored exterior and a bright red roof. A welcoming porch features two chairs and a porch railing. An American flag gently flutters beside the front door, framed by a grassy area and trees in the background.
Cabin in Grenada
4.93 out of 5 average rating, 131 reviews

The Crappie-2 bedroom cabin with spacious parking

Crappie Cabin Cozy 2BR cabin in Hugh White State Park—your ideal basecamp for Grenada Lake adventures. Sleeps 4 (Queen + 2 Twins). Full kitchen, washer/dryer, and full-size shower. Relax outside with a new firepit, gazebo, and grill. Only 5 minutes to legendary crappie fishing at Grenada Lake and Dogwoods Golf Course, plus 7 minutes to town. Boat-friendly parking included. Tags: crappie fishing, Grenada Lake, cabin getaway, boat/trailer, firepit, gazebo, golf nearby

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, 22 reviews

“The Spinney” at Enid Lake • Book now for fall!

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. New amenity as of July 2026: high speed internet/wifi! We hope you enjoy what The Spinney has to offer!

Guest favourite
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
4.91 out of 5 average rating, 95 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.

Superhost
A two-story cabin is situated among tall trees, with a wraparound deck that provides ample outdoor space. The gravel driveway leads to the entrance, while soft sunlight filters through the branches, illuminating the natural surroundings.
Cabin in Oakland
4.85 out of 5 average rating, 26 reviews

Oryza Glen Ranch at Enid Lake

A piece of mind on 12 acres in the country. Located on boat ramp road of Enid Lake. 30min drive to Sardis Lake, Grenada Lake, & Ole Miss! Recreation area with huge deck, picnic tables, pool table, ping pong, fooseball with a commercial kitchen&dining. Wraparound deck overlooks pond. Prime location w/ horse trails. Plenty of parking for vehicles and boats. Serene country getaway or great for Crappie Fishing!

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
4.94 out of 5 average rating, 170 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.

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