Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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, 122 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 favorite
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, 38 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 wrap-around deck is visible, offering a view of lush greenery and a tranquil body of water nearby. Two chairs with teal cushions are positioned on the deck, providing an inviting spot for relaxation amid nature.
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 favorite
A modern kitchen features white cabinetry and marble countertops. Stainless steel appliances are positioned efficiently. A spacious island provides additional prep space, while wood-style flooring contributes to a warm and welcoming environment. Natural light fills the area, creating an inviting atmosphere for cooking and gathering.
Home in Yalobusha County
4.92 out of 5 average rating, 26 reviews

Coffeeville getaway minutes from Grenada lake

Looking for a relaxing getaway near outdoor adventure? You have found it! Just minutes from Grenada Lake and only 30 minutes from Oxford/Ole Miss. This recently remodeled home features three bedrooms and two bathrooms with plenty of space for family and friends. Enjoy a fenced-in, pet-friendly backyard, covered parking, and a spacious back porch perfect for grilling and unwinding after a day at the lake. Gas heat, stove, and grill included—everything you need for a comfortable weekend escape.

Guest favorite
A quaint cabin is surrounded by tall trees, featuring a unique octagonal design. The exterior is clad in muted green siding with wooden shutters framing large windows. A circular fire pit is visible in the gravel area in front, enhancing the outdoor space.
Home in Pope
5 out of 5 average rating, 21 reviews

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

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.

Guest favorite
Home in Grenada
4.93 out of 5 average rating, 15 reviews

Serene Countryside Escape

Welcome to The Serene Countryside Escape. We are so excited to have you stay at our newly renovated retreat. Our charming home offers 3 spacious bedrooms and 2 full bathrooms, providing the perfect setting for relaxation and comfort. Whether you’re here for a peaceful getaway or to explore the beauty of the countryside, we hope you feel right at home.Feel free to make use of all the amenities, unwind in our cozy living spaces, and enjoy the tranquility of the surrounding area.

Superhost
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, 128 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 favorite
A three-story historic building is showcased, featuring a series of balconies with black railings. Large windows are visible on the ground floor, while bright signage is displayed on adjacent storefronts. The scene captures the essence of a vibrant downtown area, framed by clear skies.
Apartment in Water Valley
4.93 out of 5 average rating, 14 reviews

Thompson Suites

Suite 30 is centrally located in downtown Water Valley, offering easy access to shops, dining, and more. Housed in a restored historic hotel, this modern suite features one bedroom, one bathroom, a full kitchen, living room, a pull out couch, closet, washer and dryer. Enjoy views of Main Street from your private balcony in the heart of the historic district. Guests also receive complimentary day passes to the gym located conveniently next door.

Guest favorite
A modern kitchen features wooden cabinetry and a spacious island topped with a polished surface. The kitchen includes stainless steel appliances and a window allowing natural light to illuminate the workspace. Four wooden stools are arranged around the island, providing seating for guests.
Cabin in Pope
4.9 out of 5 average rating, 92 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 cozy living area is highlighted by wooden walls and ceiling, enhanced by natural light from large windows. A stone fireplace serves as a focal point, accompanied by a mounted television above. Comfortable seating is arranged near a patterned rug, creating an inviting space.
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!

Top guest favorite
A wooden dock extends over the water, featuring a seating area with chairs and an umbrella. A gently sloped ramp leads to the dock, providing access. The home, with a screened porch, is situated behind the dock, surrounded by greenery.
Home in Sardis
4.94 out of 5 average rating, 166 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 favorite
A modern kitchen features dark cabinetry paired with light countertops. An island with two wooden stools sits at the center, accompanied by stainless steel appliances. Soft lighting enhances the workspace, and a large window allows natural light to fill the area.
Home in Courtland
4.97 out of 5 average rating, 61 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 vacation rentals

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