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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, 118 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
A wrap-around deck provides unobstructed views of the private pond, surrounded by lush greenery. The wooden decking is adorned with hanging lights, enhancing the tranquil outdoor setting. A comfortable chair is positioned to invite relaxation while enjoying the picturesque scenery.
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
A unique round cabin with a green exterior and a metal roof is surrounded by tall trees. Windows feature distinctive wooden shutters, while a wrought iron door adds character. The structure is set on a stone path leading to a natural landscape.
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.

Guest favourite
The living area features a spacious sectional sofa with decorative cushions and a reclining chair. A glass coffee table is positioned on a hardwood floor, complemented by neutral gray walls. Soft lighting is provided by a ceiling fan, enhancing the comfortable ambiance of the room.
Home in Water Valley
5 out of 5 average rating, 11 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.

Superhost
A charming yellow farmhouse is shown with a welcoming front porch and white metal roof. Lush green grass surrounds the property, while vibrant red roses bloom in the foreground. A rustic wooden shed is visible to the right, adding to the property's rural character.
Home in Water Valley
4.92 out of 5 average rating, 12 reviews

Twin Lakes/Old Farmhouse B&B

Located 35 minutes from Oxford and 20 minutes from Enid or Grenada Lakes. Our 130 year old farmhouse is cozy and quaint. It will sleep 7 people . There are 2 bedrooms with antique full sized beds. The master bedroom has its own half bath. In addition to the bedrooms, there is a queen sized sleeper sofa and a twin pull out loveseat. Everything has recently been remodeled. You will love our authentic 12 foot farm table that seats 12. Laundry room and fully equipped kitchen. Wifi!

Top guest favourite
A charming farmhouse exterior is shown, featuring a white wood façade with a gabled roof. The entryway is accented by a decorative wreath and flower pots. A spacious porch is visible, leading to a landscaped yard bordered by trees under a clear blue sky.
Farm stay in Oxford
4.99 out of 5 average rating, 432 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!!!

Guest favourite
Loft in Sardis
4.97 out of 5 average rating, 29 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 favourite
Home in Oxford
4.93 out of 5 average rating, 14 reviews

Keystone Cottage

Enjoy your Oxford getaway in this cozy and stylish retreat located just 2.8 miles from Ole Miss! Perfect for game days, campus visits, or weekends exploring the town, this home gives you quick access to the university and all the action while letting you relax in a quiet, comfortable space. After a day cheering on the Rebels or strolling the historic Square, come back to unwind in a welcoming home with everything you need for a stress-free stay!

Guest favourite
A small cabin is illuminated by outdoor lights at dusk, showcasing its white exterior and steps leading to the entrance. Two chairs are positioned on the porch, providing a view of the surrounding grassy area and trees.
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.

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
4.89 out of 5 average rating, 85 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
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.

Top guest favourite
Farm stay in Oxford
4.98 out of 5 average rating, 410 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.

Popular amenities for Oakland holiday rentals

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