Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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

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Top guest favorite
The cabin is set in a secluded wooded area, surrounded by tall trees and colorful foliage. Its exterior features a combination of wood and stone, with a sloped blue metal roof. Sunlight filters through the trees, casting dappled shadows on the ground.
Cabin in Henderson
4.99 out of 5 average rating, 140 reviews

Cox Cabin “Cabin in the Woods”

Relax in this large, secluded multi-family cabin nestled on the outskirts of Chickasaw State Park on Cagle Trail. 2 King, 1 Queen, 2 Twin beds, Futon and plenty of space for personal air mattress for extra sleeping. Ride in/ride out to miles of trails in Chickasaw State Forest. Very secluded and private cabin with plenty of parking and trailers accessible. Minutes to Chickasaw Golf course, State Park amenities, and Henderson the home of Freed Hardeman Uni. We are pet friendly for a FEE per pet.

Top guest favorite
The exterior of the house is displayed, featuring a modern design with an extended roof and large front windows. A stone pathway leads to the entrance, bordered by a landscaped grassy area and scattered trees in the background.
Tiny home in Henderson
4.96 out of 5 average rating, 161 reviews

“The Casita Bonita”

Welcome to “The Casita Bonita” The pretty little house on 130 acres of pure bliss. My wonderful husband Jeremy and I bought 130 acres a few years back and is what we call “our farm” we have had countless picnics and bonfires, Just dreaming of doing something special on our land one day. That is where “The casita bonita” dream came true & it is our pleasure to be able to host guest just like you. I hope you enjoy your stay and the views of our land. Come back to see us soon. Love,Jeremy & Missy

Top guest favorite
A comfortable seating area features a brown sofa facing a rustic wooden coffee table, placed on a patterned area rug. The walls are accented with warm wood panels and metallic trim. A TV is mounted on the wall, and curtains frame the window.
Cabin in Ripley
4.97 out of 5 average rating, 101 reviews

The Outskirts

Take a break and unwind at this peaceful oasis. Quiet country studio cabin located on the outskirts of Ripley. Conveniently located 5 miles from The Red Barn event venue, 8 miles from Ripley's First Monday Flea Market and 15 miles from Blue Mountain Christian College. Only minutes away from Bennet Lake Hunting club and Dumas Lake. For dining: Enjoy a delicious meal at Simmer on Down Steak house 3.5 miles away. For Essentials: Dollar General and Clarks Country Store are only 3 miles away.

Top guest favorite
A well-lit bedroom features a wooden queen bed with a light-colored quilt and decorative pillows. Two nightstands with lamps are positioned beside the bed, and a mirror sits atop a dresser. Natural light filters through windows adorned with soft gray curtains.
Home in Booneville
4.99 out of 5 average rating, 138 reviews

Cozy Getaway Booneville, MS

You will feel right at home! Super cozy and we are 1 minute from the local park! You can walk to the park via the sidewalk in 2 minutes! Large dining and living room for tons of family time! Newly renovated spacious kitchen for all those family meals! Front porch with swing in a peaceful neighborhood for extra relaxation! Fully fenced in backyard for the kids to play in! TVs in all 3 bedrooms with Chromecast and wifi! Large tv in living room with Chromecast! 2 car carport with extra parking.

Top guest favorite
Double glass doors framed in a vibrant yellow provide access to the space. A wooden chair complements a dining area adorned with a soft table setting. Exposed brick walls and natural light enhance the warm, welcoming atmosphere.
Home in Finger
4.99 out of 5 average rating, 155 reviews

La Banque Stylish and comfy stay

Historic bank built in the 1920's restored to it original beauty. Located 5 min from Hwy 45, 8 min from K&M shooting complex and 15 min from Henderson. This is a perfect location for anyone wanting a weekend getaway or a place to rest and reset. Our space reflects peace and quiet, plenty of books to leaf through, a fireplace to warm your feet and a fully stocked kitchen. Spacious bathroom with a beautiful clawfoot tub to soak in. Come get the unique experience of sleeping in bank vault!

Top guest favorite
A serene lake is framed by vibrant autumn foliage and tall trees, reflecting the colorful surroundings. A white fence runs along the edge, enhancing the natural beauty of this tranquil scene, inviting peace and relaxation.
Home in Henderson
5 out of 5 average rating, 137 reviews

The Oliver Lakehouse

Nestled in the rolling hills of Chickasaw State Forest, the Oliver House is located on 38 acres with 2 lakes, 2 kayaks, 2 canoes and the sweetest muscovy ducks you will ever meet. Oliver is the oldest duck the inspiration behind our name! Our place is the perfect place to unwind, unplug and to just be in nature. Whether you prefer fishing, napping on the swing or reading a good book out on the deck, we are sure you’ll find it all here. Take a deep breath, relax and enjoy. We welcome you!

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.

Top guest favorite
A living room features a dark blue couch adorned with decorative pillows, positioned near large windows dressed with light curtains. A coffee table sits centrally, displaying a stack of books and small plants. Wall sconces and a mirror add to the room's inviting ambiance.
Cottage in New Albany
4.9 out of 5 average rating, 662 reviews

The Cottage in Downtown New Albany, MS

Come and enjoy The Cottage in Downtown New Albany, MS! This newly renovated property boasts detailed interiors and modern luxuries, while still maintaining the cozy comforts of a weekend cottage. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

Top guest favorite
The exterior of a newly renovated home features a charming front porch supported by decorative columns. Large windows allow natural light to illuminate the space, while a well-maintained lawn and neatly arranged shrubs enhance the welcoming entryway.
Home in New Albany
4.99 out of 5 average rating, 139 reviews

The Queen on Cleveland

Come and enjoy The Queen on Cleveland in Downtown New Albany, MS! This new AirBNB is a sister property to “The Cottage”. This newly renovated home boasts detailed interiors and modern luxuries. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

Guest favorite
A wooden deck extends outward, providing a view of a vast, open grassy field. A lone tree stands in the distance against a backdrop of scattered clouds and blue sky, with greenery stretching toward the horizon.
Cabin in Shiloh
4.99 out of 5 average rating, 116 reviews

The Shiloh Retreat

Love being outside but don't love tents to sleep in at night? Come to The Shiloh Retreat for a relaxing place to stay on over 12 acres only 2 minutes from Shiloh National Military Park, 18 minutes from Pickwick Lake, 12 minutes to the Tennessee River, and 13 minutes from Adamsville, Tn home of Bufford Pusser. - Plenty of space to park your boat or trailer. - Smal kitchenette with refrigerator, sink, and a microwave, oven, air fryer combo.

Guest favorite
The exterior of the home is presented, featuring a welcoming entrance with a star motif. Two chairs are situated on the porch, and greenery surrounds the area, creating a comfortable environment for guests and pets. Natural light filters through the windows, enhancing the inviting facade.
Home in Holly Springs
4.83 out of 5 average rating, 224 reviews

Gallop-Inn Bungalow

PETS are welcome but please no more than 2 pets. Super easy self check in with keypad. Great location just outside the city and just a short drive to Historic Downtown Collierville, TN or how about a 30 minute drive to Downtown Memphis/Beale Street, Tunica Casinos, and Graceland. Plenty of Acreage for your pets to exercise. Enjoy the local sights of the area like Pickwick Lake and State Park less than an hour drive. Enjoy all the conveniences of home.

Top guest favorite
The sleeping area features a queen bed with a rustic quilt, accented by supporting wooden nightstands and a bench at the foot. Warm wood paneling and a decorative star motif are visible on the floor, enhancing the cozy barn atmosphere.
Barn in Pocahontas
5 out of 5 average rating, 206 reviews

The Bedroom in the Barn

Welcome to Smith’s Farm Horseshoe Haven. A wonderful place to step back to the times of days gone by, where life is a little slower and simpler and enjoy a stay in our rare little gem "The Bedroom in the Barn" Lose yourself in the country, unwind and smell the fresh air and listen to the sounds of horses around you. A sweet experience you won't forget!

Popular amenities for Ashland vacation rentals

  1. Airbnb
  2. United States
  3. Mississippi
  4. Benton County
  5. Ashland