Holiday houses in Oakfield

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Top-rated holiday rentals in Oakfield

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Top Guest favourite
A spacious bedroom features a comfortable bed with crisp white linens. Light filters through sheer curtains on either side of two windows. A wooden nightstand holds a glass lamp, while a woven basket and a clothing rack add functional elements to the inviting space.
Apartment in Jackson
4.96 out of 5 average rating, 180 reviews

The Waffle House: Historic Full Downtown Apartment

The apartment is called Waffle House because it was the home of Waffle House founder Joe Rogers. The space is a full apartment with kitchen, laundry, living room, bathroom and bedroom with a separate entrance. Located on W Deaderick it’s just a short walk to Restaurants , Farmer's Market, and Hub City Brewing. I am the brewmaster at Hub City Brewing & Rock’n Dough Pizza + Brewery, and my wife works for Hitachi Energy. We live in the downstairs unit so are nearby if there is anything you need.

Top Guest favourite
The studio features a comfortable queen size bed covered with a grey quilt and decorative pillows. A small desk with a chair is positioned next to the bed. Warm lighting enhances the cozy atmosphere, while a kitchenette is visible in the background.
Guesthouse in Henderson
4.95 out of 5 average rating, 526 reviews

Studio Apt on 5th

The Studio on 5th in Henderson, TN is close to Freed-Hardeman University (3/4 mile) & 25 min. from Jackson. This studio w/ 1 queen size bed, 1 bath & kitchenette guesthouse is good for couples & solo adventurers. It is located in a quiet neighborhood next to the host's family home. Includes: Off-street parking, complementary coffee & snacks, Wi-Fi, soaps, shampoo, fresh towels & linens, & outdoor seating. **Simple Check in & Check Out! No "to do" lists!** **Super hosts for over 6 years!**

Guest favourite
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
4.97 out of 5 average rating, 125 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 favourite
The exterior of a rustic cottage is shown, featuring a welcoming porch with two metal chairs. Lush greenery surrounds the entrance, and a path leads to the front steps. The building has a light-colored facade and a classic metal roof, set against a peaceful rural backdrop.
Guesthouse in Bradford
4.92 out of 5 average rating, 119 reviews

Spacious and Private Guesthouse in the Country

Rustic, refined cottage with all amenities. 1930s farm home updated for modern life. Soak in the peace and quiet. Perfect for EXTENDED STAYS (CHECK DISCOUNTS!), artists/writers, looking for quiet inspiration. Full kitchen, Keurig coffee-maker, washer/dryer, stereo. Unlimited Internet through local company (TEC). Central heat/ air. Large screen TV w/ Amazon Prime. No smoking or pets, please. No minor children. Adults only. Very Private backyard. Welcome persons of all beliefs & backgrounds.

Guest favourite
A covered front porch features two yellow rocking chairs positioned next to a small round table. A striped outdoor rug lies beneath them. Lush plants are placed in decorative pots, enhancing the welcoming atmosphere of this vintage bungalow.
Bungalow in Milan
4.97 out of 5 average rating, 423 reviews

The "Heart of Milan" Guest House

This is a vintage 1920's craftsman style bungalow that has recently been redecorated. You will be renting the whole house to include a large master bedroom, a second private bedroom, two bathrooms, a fully equipped kitchen, office, living space and common room with an extra twin bed. Washer and dryer included. Hardwood floors throughout the home. This house is an ideal rental for executives or travelers who are looking for a more home like environment or anticipate an extended stay.

Top Guest favourite
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
5 out of 5 average rating, 128 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 favourite
A spacious home is showcased, featuring a combination of stone and brick exterior elements. The entrance is highlighted by large, inviting wooden double doors flanked by greenery. Well-maintained landscaping surrounds the home, complemented by a manicured lawn and the welcoming symmetry of shuttered windows.
Home in Jackson
4.99 out of 5 average rating, 129 reviews

I'm Goin' to Jackson

Clean and cozy home less than 10 minutes from I-40, Union University, and north Jackson shopping, parks, restaurants, and entertainment. Great layout comfortably sleeps up to 8 guests yet cozy enough for 1-2 people. Our family frequents Airbnb properties when we travel and have brought that experience to our home to make it as comfortable as possible. Feel free to use the elliptical or venture outside for a walk or bike ride to see one of two water wheels and ponds in the neighborhood.

Guest favourite
A scenic view captures the entrance to The Farm at Casey Jones Village, framed by a wooden archway. Expansive green fields are dotted with rustic buildings, including a barn and sheds. A well-maintained path leads past vibrant sunflowers and seating areas, inviting relaxation amidst the natural landscape.
Bungalow in Jackson
4.96 out of 5 average rating, 179 reviews

Pearl Cottage in Casey Jones Village

Step back to a gentler time in this pre-civil war shotgun house in the historic Casey Jones Village. A perfect getaway spot for couples for their honeymoon or anniversary or people wanting to get away for a spiritual retreat. Pearl House is complete with a claw foot tub, a huge shower and his and her robes. There are some wonderful books to read at Pearl, many about history and a great collection of cookbooks. It features a complete kitchen, washer and dryer; all the modern amenities.

Guest favourite
Home in Jackson
4.95 out of 5 average rating, 298 reviews

"Hospitality House"3 br 2 bth house N Jackson TN

You are renting the entire property. 3 bedroom 2 bathroom house with patio. Located in north Jackson close to I 40, restaurants, and shopping. Great quiet Cove neighborhood safe for evening walks. Will accommodate families, traveling nurses, students, or corporate traveler. No pets. Exceptions can be made, contact host. No large parties or events can be hosted. 10 or more pl. Non smoking home smoking in this property will result in $250 cleaning fee Quiet time between 9pm-6am

Top Guest favourite
A welcoming living room features a grey sofa and loveseat, arranged around a dark coffee table. A soft area rug is laid over warm wood flooring. Natural light filters through sheer curtains, enhancing the space, while decorative elements include a shelf and wall art.
Home in Jackson
4.98 out of 5 average rating, 144 reviews

Swan House

This two bedroom, newly renovated 1950’s home exhibits historic midtown charm paired with modern style. Our quiet, dead-end street offers the space to get away, while being conveniently located ½ a mile from the Hospital and right around the corner from the local shops and restaurants of downtown Jackson. Two minutes from the bypass for a quick drive up north; ten minutes from Union University.

Top Guest favourite
The kitchen features a blend of modern and vintage elements, with dark cabinetry contrasting against wooden accents. A central island with a marble top is surrounded by high stools. Pendant lights illuminate the space, enhancing the inviting atmosphere for cooking and dining.
Apartment in Huntingdon
4.99 out of 5 average rating, 102 reviews

Huddleston Hall

Huddleston Hall is in the heart of Downtown Huntingdon in the upstairs of a historic building that dates back to the late 1800s. Located within walking distance of restaurants, coffee shops, boutiques, and two theaters...The Dixie Performing Arts Theatre and Court Theatre makes it the perfect spot.

Top Guest favourite
A welcoming front porch is shown with two rocking chairs positioned beside potted yellow flowers. A bench sits to the side, and a wooden railing surrounds the porch. Lush greenery is visible in the background, enhancing the peaceful atmosphere.
Home in Jackson
4.97 out of 5 average rating, 181 reviews

Welcome to The Lily Pad!

Keep it simple at this peaceful and centrally-located place. Located just minutes from downtown Jackson, Jackson Madison County General Hospital, The Lift, The Ballpark at Jackson, shopping and restaurants, The Lily Pad is ready for your overnight stop, weekend getaway, work trip or extended stay.

Popular amenities for Oakfield holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Madison County
  5. Oakfield