Holiday rentals in Chancellor

Downtown Private Suite

Enjoy your own private entrance into the home through the back patio, leading directly into a private living room with an attached master bedroom, bathroom and walk in closet. The home is centrally located near downtown Enterprise. Please note: This is a shared home; however, no living spaces are shared. A locked door separates both sections of the home to ensure complete privacy. Recreational drug use and smoking of any kind are strictly prohibited inside the home and anywhere on the property.

Beautiful and Spacious 3 BR/2BA with KING bed

Our "Home Sweet Home" is a beautiful full residential 3 BR/2 full BA home in a quiet family-oriented neighborhood. Master BR: 1 King bed, BR has jacuzzi tub 2nd BR: 1 Queen bed 3rd BR: 2 Twin beds Living room: Comfortable sofa and optional rollaway bed if needed, 55" Smart TV with all the streaming apps, kid games Kitchen: Fully Stocked Coffee Bar, cookware, double oven, microwave, dishwasher, plates, glasses, wine glasses and more. Garage: 2 car private Entry Way: Keyless Entry Pet Friendly

The Byrd Nest in the Heart of Downtown Enterprise

Welcome to our little home away from home in the heart of Enterprise! Our century-old house blends historic charm with modern comfort and convenience. Just steps from downtown restaurants, shops, pubs, and local attractions, it’s the perfect spot for guests who want to experience everything the Boll Weevil City has to offer. And it's only a short drive to the Fort Rucker gate! Whether you’re visiting for work, family, or a weekend getaway, we’re excited to host you and hope your stay is great.

"The Clubhouse" Pvt Apt w/Mstr BR & 2bed Kids Loft

I spent 2 years custom building this apartment to be used exclusively as an Abnb rental. It was handcrafted using tongue & groove pine milled here in AL. All of the oak/pine used for the trim, cabinet doors, and custom furniture were milled in VA using my stepfather's personal sawmill with lumber harvested both from my property here in AL, and my families property in VA. Even the door/drawer pulls and switch/outlet covers were hand forged in PA by an Amish guy at his home forge in his basement.

Come Chill at our Cute 2 bedroom Cottage

Enjoy yourself in this completely renovated and remodeled cottage located in the heart of Enterprise, AL. This space has been designed with the guest in mind. We offer full kitchen, laundry, high speed fiber optic internet, and all new furnishings in this modern take of an original WWII era home. We aim to please and, although new to Airbnb, we have hosted over 1000 - 5 Star trips on other P2P platforms. You'll love coming back to the Come Chill cottage. New Pickleball Courts 3 min away!

BEST VALUE Private Suite; "Clean & Peaceful"

"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;

Relax at the Ridge | 4BR/3BA

Welcome to Relax at the Ridge. This home is conveniently located right outside Ft. Rucker (Faulkner Gate) and minutes from Downtown, and Johnny Henderson Park. lt is also only about an hour and half away from the world's most beautiful beaches, the Gulf of Mexico. With 4 bedrooms and 3 bathrooms, it has plenty of room for families visiting Enterprise. The entire home is exclusively yours to enjoy. Equipped with smart technology and enhanced security measures, this could be your perfect stay.

The Gulf Breeze cottage

Built in 1945, this family-friendly historic cottage, welcomes everyone. Renovated historical home in 2019. Cozy space with beautiful wood floors perfect for a small family or 3 couples. Great area to stay that’s close to Panama City Beach, Florida. Day trip to a local spring or enjoy one of the many local parks or lakes in the area. Also close to fun places for the kids to enjoy. Check out our guidebook and see everything the area has to offer. Stay here for a peaceful small town charm

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!

Perfect for Big Families, Sleeps 14, Fort Rucker A

Located in one of Enterprise, AL's finest neighborhoods, Cotton Creek, this 4 bedroom home offers an exceptional stay. With 3 King beds, 4 Full beds, 2 queen sleeper sofas, and 2 baths, it's ideal for larger families on a PCS or visiting Enterprise. Just minutes away from Fort Rucker, John Henderson Family Park, and the Enterprise Country Club. Enjoy the convenience of smart technology and security throughout the entire home, allowing you to unwind and make the most of your time.

River Retreat in Geneva, Alabama

Nestled along the picturesque banks of the Choctawhatchee River, our charming River House in Geneva, Alabama, offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a peaceful weekend getaway or a longer vacation, this river house promises a rejuvenating experience like no other. Read on to discover what makes this property a hidden gem in the heart of the South.

Family Home 4BR | King Bed | Fast WIFi | PCS/TDY

Perfect for PCS, TDY, training, or visiting family at Fort Novosel. This furnished farmhouse-style home sits on a quiet corner lot off Rucker Blvd with quick access to base, dining, and shopping. Enjoy high-speed Wi-Fi, a full kitchen, laundry, and a comfortable setup for extended stays. Great for military guests, families, and long-term travelers alike. Discounts available.