Vacation rentals in Headland

Comfy 3 bedroom house with hot tub and game room.

Relax and unwind in this space, or even come to work or play. You will have the entire 3 bedroom, 2 full bath house to yourselves. Equipped with washer/dryer, kitchen, hot tub, work space, Wi-Fi, and even a little bar with ping pong table & dartboard. This is our house we have been remodeling and use as our own little getaway on date night, it’s far from upscale fancy, but it is cozy and with a soak in the hot tub can even be romantic. Welcome gift provided, message with any special requests.

State Park Cottage - Quiet Yet Centrally Located

Cottage is in the middle of a 2 1/2 acre wooded lot. It is in the middle of town, but your stay will be quiet and private. The neighborhood park, Solomon Park, is just one block away. Neighborhood is great for a stroll or run. You will be a short car ride from more than a dozen places to eat, grocery stores and shopping. We live on the property, but the cottage is a detached structure. If you need anything at all, we will be close by to provide as much or as little assistance as need

Home in Heart of Headland

Quaint cottage located on the grounds of the beautiful and historical Covington Home that was built in 1902. Headland, AL better known as the “Gem of the Wiregrass” was rated one of the safest cities in AL in 2019 and is a designated Main Street community. The cottage is walking distance to the square where you will find soft music playing as you stroll the streets, picturesque oak trees, stylish boutiques and cuisine to fit any taste pallet. It is less than 10 miles to the Dothan Airport.

Just Simply Convenient

This 3/2 home is convenient to most major shopping centers and movie theaters. Great restaurants and Winn Dixie/Publix grocery stores are within 5 min. Westgate park is a 7 min drive. We provide WiFi and Roku TVs in den & all bedrooms. We also provide individually wrapped bath soap, dishwasher powder, laundry detergent and fabric softener that should be enough for short stays and a nice starter for extended stays. Keurig and a standard coffee pot is provided along with a variety of K-cups.

Cozy Cottage in the Pines

Enjoy a quiet stay just outside of town on a farm! Listen to the breeze whisper through the pines and relax in this peaceful country setting. The cottage is 2 miles north of Cottonwood and is just under 10 miles to The Ross Clark Circle in Dothan. Dothan has a lot to do…..shopping, dining, and entertainment. Also, the cottage is only a few miles from the Florida line and the Georgia line if you’re going there for something fun! WiFi is fast so working from the cottage is easy as well!

Bridal Cottage at Adams Acres

Relax & unwind at the Adams Acres Bridal Cottage, where modern comfort meets countryside charm. 🛌 Features You’ll Love: • Comfortable king-size bed in private bedroom + pull-out queen bed in sitting area • Spacious sitting area and vanity stations for getting ready • Private bathroom with a rainfall shower. Just minutes from Dothan, Adams Acres Bridal Cottage offers peaceful mornings and stunning sunsets with a nearby park featuring a walking trail, pickle ball court & more

Juju’s Pond House on Smith Pond

Take it easy at this unique and tranquil getaway located on 100 acres and nestled quietly on a private pond. The house was originally built in 1921 and in 2018 we had the house moved down to the pond and did a full renovation while preserving as much original character as we could. Enjoy your morning coffee and watch the sunrise from the screen porch swing or one of the docks at the pond. The property has nature trails to explore, fishing, and plenty of wildlife.

Claire’s Cottage with privacy gate

Everything you need in a quaint, modern space located on 7 secluded acres with a privacy gate only minutes from the Ross Clark Circle and downtown, Wi-Fi, Smart TV with YouTube TV subscription included (over 70 channels), brand new fridge, spacious rooms. Washer and dryer available. We allow pets on a case by case basis and charge a one time $10 fee per pet upon guests arrival. We also offer EV level 2 charging (40 amp) for a flat $10 fee.

The Blackshear Place

A 100 year old house on land that was homesteaded in the 1800’s. Plenty of character, peaceful, private and quiet. 18 minutes from Ross Clark Circle, Dothan Al., 15 minutes from Headland Al. 19 minutes from Blakely Ga. 15 minutes to Log Cabin Restaurant in Georgia and Huggin Molly’s in Abbeville Al. Nearest grocery and gas is 10 minutes in Columbia Al. No WIFI hot spots work well Verizon tower 2 miles away

Hartford Art Studio and Loft

This treasure is a stand alone art studio with a loft surrounded by beautiful lawn and gardens. The Studio is 45 feet (read close) to the house. There are agricultural fields on three sides. The artist, Beverly Mayfield, is now deceased, but has filled the studio with masterful paintings.

At my place on Foster Apt.1

Located in Old Downtown Dothan, convenient to shopping, dinning, entertainment and local coffee shops. 20.6 miles to Farley Nuclear Plant, 2.2 miles to Southeast Health Medical Center, 4.2 miles to Alabama College of Osteopathic Medicine.

Little House Behind the Cedars

Cute studio space in our front yard, that sleeps 4 with a half kitchen (NO STOVE OR OVEN) in a quiet country setting. Feels like you’re way out in the country but are inside the city limits. Minutes to all Dothan has to offer.