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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, 120 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 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
4.84 out of 5 average rating, 91 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
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 favorite
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, 20 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 favorite
A charming guest house is framed by lush greenery and a well-maintained lawn. The wooden structure showcases a screened porch with red accents, along with a welcoming American flag. An outdoor seating area is visible, inviting relaxation in a tranquil environment.
Guesthouse in Como
4.98 out of 5 average rating, 161 reviews

Heavens Trees: Small town Guest House

Cute comfortable guest house in small Mississippi town. Como is 40 miles south of Memphis and 40 miles from Oxford , MS. Take in a Ole Miss game or check out Beale St. We are within walking distance of Main Street in Como where you can find great restaurants and antiques. Coffee, tea and continental breakfast with snacks and bottled water provided. Swim in our lovely pool, sip your morning coffee sitting on the screened in porch overlooking the pool and pasture with 4 mini horses.

Guest favorite
An open concept loft is displayed featuring two king beds with white linens. A leather sofa and two colorful chairs offer seating in the living area. Exposed brick walls and modern artwork complement the space, with wooden furniture providing distinct dining and coffee table options.
Loft in Sardis
4.97 out of 5 average rating, 32 reviews

Livie's Loft

This unique place has a style all its own. Stay in a stylish newly renovated Main Street Loft in Sardis, MS. Walk to restaurants and a short drive to I-55. Only a few minutes away from the beautiful Sardis Lake. Close to Oxford. Open concept loft with 2 king beds and memory foam mattresses. Relax on the leather sofa and enjoy watching the smart tv. Enjoy a home cooked meal in the full kitchen and custom kitchen table. Private bathroom with custom barn doors has large tile shower.

Guest favorite
A single-story cabin is framed by lush greenery, featuring a classic metal roof. A wooden porch offers seating with an American flag displayed prominently. Windows allow natural light to enter, while the gravel driveway complements the rustic exterior.
Cabin in Grenada
4.77 out of 5 average rating, 53 reviews

The Bass Shack-2 bedroom cabin w spacious parking

Bass Shack Pet-friendly rustic cabin built for fishing, hunting, and golf trips. Sleeps 3 with 2 bedrooms (Queen + Twin) and 1 bath. Full kitchen, washer/dryer, and free parking. Grill out, relax in the gazebo, or gather around the firepit after a day outdoors. Located just 5 minutes to Grenada Lake & Dogwoods Golf Course and 7 minutes to town. Boat/trailer-friendly parking. Tags: sportsman cabin, hunting, fishing, pet-friendly, firepit, boat/trailer parking

Guest favorite
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, 87 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.

Guest favorite
A charming cottage exterior is framed by lush greenery, featuring a welcoming porch with a small table and two chairs. A rocking chair is positioned nearby, along with a swing. Large windows allow natural light to brighten the entrance, inviting guests to enjoy the serene surroundings.
Cottage in Oxford
4.96 out of 5 average rating, 103 reviews

Firefly Cottage

Beautiful, newly-renovated cottage surrounded by woods, steps away from private lake. Easy to be isolated in this roomy studio with vaulted ceiling and fans, fully outfitted kitchen, queen bed and futon couch. Large shower. Hi-speed Wi-Fi and Roku TV. Porch with seating; charcoal grill & fire pit. Owners' residence on property, plus dogs and chickens. 7 miles from Oxford square, 8 miles from campus.

Top guest favorite
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, 104 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.

Guest favorite
The exterior of a brick home is presented, featuring a wide porch with several chairs. A well-maintained yard is visible, accompanied by bushes and trees that provide shade. The driveway leads to a garage, partially obscured by foliage, maintaining the serene environment of the property.
Home in Grenada
4.88 out of 5 average rating, 24 reviews

Little Sister's Place

Peaceful 3-bedroom, 2-bath brick home near I-55 and downtown Grenada. Includes a full kitchen, formal dining room, two living areas, high-speed Wi-Fi, and free parking. Relax on the back deck or fire up the BBQ grill in the spacious yard. Ideal for families, professionals, and travelers seeking comfort and convenience in a quiet, tree-lined neighborhood.

Top guest favorite
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, 160 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.

Popular amenities for Oakland vacation rentals

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