Holiday houses in Headland

4.95 out of 5 average rating, 128 reviews

Guesthouse in Dothan

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 needed.

5 out of 5 average rating, 53 reviews

Home in Headland

Dixieland Delight

BRAND NEW 2bed/2 bath peaceful getaway in the heart of historic and charming Headland, AL! Open-concept living area. Ample seating and a large flat-screen TV! 2 bedrooms and 2 full baths. The master bedroom offers a king-sized bed and an en-suite bathroom. The 2nd bedroom has a full-sized bed and an additional bathroom is conveniently located in the hallway. Explore charming downtown Headland, visit the nearby Headland Square, or head into Dothan for shopping, restaurants, and entertainment.

Superhost

Townhouse in Dothan

4.85 out of 5 average rating, 155 reviews

Stay & Play w Gameroom 2BR/2.5BA Short & Long Term

This 2 story townhome, over 1,400 sq ft, sleeps 6 and is centrally located in Dothan, AL with multiple parking. Located 5 minutes from hospitals, RTJ+DCC golf courses, Westgate Recreation Park and area shopping and restaurants. Keyless entry for self check-in. Newly renovated and fully equipped kitchen with new stainless steel appliances, granite, washer/dryer, fast/free wifi & more. Enjoy in home gameroom with 6ft. pool table, ping pong, ring toss & more. Long & short term stays are welcome!

Guest suite in Enterprise

4.98 out of 5 average rating, 556 reviews

BEST VALUE - No Cleaning Fee

"Relaxing, calm, quiet, peaceful"--all used to describe the 1,200 sq. feet of guest space attached to our home--Read a complete description under "The Space." The private guest suite includes a family room, two bedrooms and bath on our micro-farm just 4 minutes from Fort Rucker and Enterprise. Southern hospitality at its best--Read our reviews! Ammenities include personal-size fridge, coffee, microwave, pool table, WiFi, TV, DVD, Wii, games and toys; laundry room; Handicap/ADA accessible;

4.99 out of 5 average rating, 116 reviews

Tiny home in Headland

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.

4.93 out of 5 average rating, 144 reviews

Twin Pines | Luxury Getaway

Welcome to Dothan's Gem! A beautifully designed dream home! Bringing the whole family? Working remotely? Rest assured, you'll have high speed internet no matter what, with speeds up to 500mbps! While there's plenty of privacy, this location makes it easy for you to get around You are only: 4 mins to Flower's Hospital 5 mins to Westgate Recreation Park 5 mins to Forever Wild Trails 10 mins to the heart of Downtown Dothan 1.5 hrs to PCB & surrounded by Dothan's best restaurants!

4.95 out of 5 average rating, 255 reviews

Cottage in Dothan

The Oak Nest Garden District

Our cozy cottage home is 900 square feet and it is located behind our home in the beautiful garden district-a quiet, peaceful neighborhood. This adorable cottage has a full, spacious kitchen(sink, refrigerator,stove/oven, microwave, dishwasher basic cooking needs),living room, dining room, bar seating,bedroom with a queen-sized bed, walk-in closet, and stack unit washer/dryer. We are convenient to ACOM and 30 minutes to Fort Rucker. There are 2 nearby parks as well as hospitals.

5 out of 5 average rating, 113 reviews

Townhouse in Dothan

Special Rates For Summer! Chadwick Townhouse

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, you're just moments from championship golf at RJT and DCC, thrilling water fun at Water World, exciting games at the Westgate Baseball and Tennis Complex, the serene beauty of Forever Wild trails, and conveniently close to both area hospitals. Unwind in comfort with a fully equipped kitchen, perfect for whipping up delicious meals and stay connected with blazing-fast Wi-Fi.

4.99 out of 5 average rating, 194 reviews

Cottage in Dothan

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.

4.98 out of 5 average rating, 64 reviews

The Copper Door Cottage*No Cleaning Fee*

Excellent central location! Minutes to downtown Dothan. Plant Farley 30 min away. Just an hour & 25 min drive to beautiful PCB. Quiet and quaint neighborhood. Cozy, simple, and family friendly home with everything you need! SUPER comfy beds including a king DReAMCLoUD and a queen BEaUtySLeEp! Super HIGH SPEED FIBER OPTIC INTERNET. A 55” smart tv in the living room and a 32” smart tv in the king bedroom! Make yourself at home! Excellent communication with Host.

4.91 out of 5 average rating, 450 reviews

Apartment in Dothan

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.

4.98 out of 5 average rating, 144 reviews

Tiny home in Slocomb

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The spacious kitchen has new appliances. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Novosol is 12 miles away.

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Other great holiday rentals in Headland

4.79 out of 5 average rating, 102 reviews

Netty's Nest

RickRating, 5 stars2 weeks ago

I was looking for a relaxing getaway for my wife’s birthday where she could just lounge by the pool. Netty’s Nest definitely fit the bill. The house was clean and the pool was refreshing. The master bed was extremely comfortable and everything was as described. The host was extremely responsive and helpful.

5 out of 5 average rating, 41 reviews

Garden District Hideaway, King Bed

WenxianRating, 5 stars1 month ago

Dora is a very nice and friendly host, who kept me closely informed about her place and our stay in Dothan. Her house is very clean and well maintained, everything is good and as we expected, we had thorough enjoyed our visit to AL and had a wonderful three-day stay at this lovely home, thank you so much Dora!

4.99 out of 5 average rating, 75 reviews

Loft in Headland

Downtown Main St. Gem - Loft 5

GentryRating, 5 stars1 week ago

I really enjoyed my stay! The loft is very cozy and relaxing. Melissa was very attentive. Tye ceiling in the bedroom is lower but I didn't notice have an issue being an average size man in height, thus I did not bump my head on those old beams. I highly recommend staying here, you will not be disappointed!

4.75 out of 5 average rating, 114 reviews

Four bedroom home steps away from Westgate Park!

JonathanRating, 5 stars1 month ago

Great place to stay in a very quiet and safe neighborhood! Place was clean and had everything we needed for our short trip visiting family. Great location very close to restaurants and groceries. Amanda was a great host and very responsive!

Superhost

4.9 out of 5 average rating, 61 reviews

Baker’s Stay & Play

DanielRating, 5 starstoday

Mrs. Sandra is an amazing, classy southern young lady! Nicest host I have ever had the pleasure of working with. She responded immediately when I needed her. Her home was a blessing! Spotless, comfortable and my kids loved all the games and pool! 10 STARS!!!

4.95 out of 5 average rating, 80 reviews

Cabin in Ashford

The Cabin

AdamRating, 5 stars4 months ago

My wife and I were looking for a peaceful escape to disconnect from the world and reconnect with each other—this cabin was the perfect place for it. After unloading the car and taking a quick walk around, we never felt the need to leave. It was comfortable, quiet, and surrounded by nature. Birdwatchers will love the variety of feathered visitors, and the soothing sounds of the outdoors make for a truly relaxing stay. Even with the distant hum of Dothan Motor Speedway practice for a few hours, the serenity remained. We heard about the neighborhood cow that likes to escape and pay a visit, though we didn’t get to see it this time. We’re already looking forward to our next stay in the near future!