Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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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, 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 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, 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 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, 93 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
4.94 out of 5 average rating, 36 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 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, 25 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 favourite
Home in Pope
5 out of 5 average rating, 21 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 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, 163 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 favourite
A comfortable living area features a sectional sofa adorned with decorative pillows. A stylish rug in a warm yellow hue covers the floor, complemented by a standing lamp next to a small side table. Natural light enters through yellow-curtained windows.
Home in Grenada
4.92 out of 5 average rating, 13 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 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
4.9 out of 5 average rating, 93 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 cozy outdoor area features a gas fire pit surrounded by four chairs with red cushions. A hot tub, illuminated with soft blue lights, is nearby, creating a relaxing ambiance. Decorative lights hang in the background, enhancing the evening setting.
Cabin in Oxford
4.97 out of 5 average rating, 101 reviews

Cheerful House with POOL, Hot Tub, and Fire Pit

Spend some quality time with your family by relaxing at our cottage. There is a hot tub and TV outside for you to watch the football game or just listen to music. There is also a gas fire pit and a outdoor kitchen with a gas grill. Come make a wonderful family memory or bring your best friends for a weekend get away. Swimming Pool close October to May each year. No Parties, unless approved before booking.

Guest favourite
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!

Popular amenities for Oakland holiday rentals

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