Holiday rentals in Toomsboro

Adorable 1-bedroom guesthouse on the river

Guesthouse at TURKEY HILL COTTAGE Relax in this calm, stylish woodland retreat just 6 miles off 1-16 on the Oconee River. Dublin is 15 min. away, VA Hospital & Fairview Park Hospital 20 min. Southern Pines Rec. prk, 12 min. Extra large bedroom with queen bed and loft. Can accommodate at least 4 adults, 2 children. Full kitchen with bar. Amenities include internet, cable, VCR, HVAC. All linens, dishes, & cookware provided. Apartment located above separate garage. Community boat ramp available.

Granny’s House-3/2- 25ish min Milledgeville/Dublin

Welcome to Granny’s House; your peaceful and comfortable retreat. This charming 3-bed, 2-bath home is designed with families in mind and comfortably sleeps 7(up to 9) see notes on beds. The warm and inviting atmosphere makes Granny’s House feel like home. The layout includes two separate living spaces, giving your group plenty of room to spread out. The home is furnished with comfort and practicality in mind. Granny’s House is the perfect place to relax, reconnect, and make lasting memories.

Best Dam View at Sinclair! Big Water Pets Welcome

Lovely sunrises & moon views. 5 min to downtown, 2 min from The Club at Lake Sinclair & DG. Sleeps 6-8 people, (air mattresses/beds) Perfect for entertaining with outdoor dining areas. Fire pit with lots of seating. Big views of water & nearby sandbar, across from an island with beachfront space. Tons of amenities you may need, including a pack-n-play. For the hot-natured, white noise lovers we have large floor fans! Kayaks & paddleboards on site & Rubber Dockie that will entertain the kids.

Old Capital - Prof. Design, Mins to GCSU, DT, Lake

Enjoy comfort at Old Capital, our professionally designed retreat, just minutes to Downtown Milledgeville, Georgia College, and Lake Sinclair. This bright, modern home sleeps 5 and features high-speed WiFi, smart TVs, a fully stocked kitchen, and comfortable bedrooms designed for easy, relaxing stays. ☀ 5 min drive to Downtown Milledgeville ☀ 5 min drive to GCSU ☀ 10 min drive to Lake Sinclair Meredith and I are local hosts with 4.99★ ratings across our homes and hundreds of happy stays!

Historic Macon Luxury Lodge with updated decor

Nestled in the heart of town, our Historic Macon Lodge has everything you need to relax and feel like you have escaped into nature. 3 bedrooms, 2.5 bathrooms, with 2 stone fireplaces and large glass windows. There is a spacious backyard with a fire pit and breathtaking wooded walking trails to a nearby historic Grotto. This Lodge is perfect for romantic couples and families with small children. There will be no parties, groups or gatherings allowed. Please acknowledge in your message

Renovated 1928 cottage on a former asylum campus

Into the macabre? Stay on the campus of what once was the largest mental asylum in the world. Stay in a fully renovated craftsman, 1920's cottage situated on the corner of a large pecan grove, across from the Central State Hospital infirmary. Walking, driving or trolly tours are available to learn all about the history of one of the nation's oldest and largest institutions for the mentally ill. Note: Buildings are closed to the public. There are no tours inside buildings.

Cottage at the Blue Goose

The Cottage at the Blue Goose is the perfect space to relax or work remotely. It's surrounded by established gardens full of perennials and native plants. From the front porch rocking chairs enjoy watching the the hummingbirds dart from flower to flower. The Cottage also has a Southern style screened in porch with haunt blue ceiling and lots of comfortable seating. Parking is under the lighted breezeway connected to the cottage.

Cozy Wooded Cabin w/ Tub, Rain Shower & Pergola

Fall Tiny House Hideaway! 🍂 Escape to this Milledgeville gem in a quiet retreat just 5 mins from downtown. Embrace the crisp autumn air with cozy evenings by the fire pit or relaxing under the pergola. Indoors, soak in the luxury tub with a Smart TV, or step outside for a rinse in the private outdoor rain shower under the stars. Perfect for couples or friends looking to sneak away, connect, and enjoy the season!

The Farmhouse

Peaceful farm house cottage. Enjoy a weekend in the country just a few minutes from Milledgeville, and a short drive to Dublin or Macon. Safe, warm, and cozy. You and your family will enjoy chickens crowing in the distance, watching horses graze from the front porch, and the spacious yard providing plenty of safe, secure parking.

719 Wildwood Ranch 2 Bedrooms 3 beds

Take it easy at Wildwood, a unique and tranquil space. This 2 bedroom 2 bath cottage with a pull out sleeper sofa is tucked away and surrounded by nature, yet conveniently located next door to a wedding venue and just minutes from local activities. We promise you won't want to leave.

The Little Pink House

Cozy little home that is a historical landmark unique to the Sandersville area. Great outdoor living space to relax and unwind. Home has full amenities and everything you may need. 2 Bedroom, 2 Full Bath, and Pullout couch, home sleeps total of 6.

Cyprus Custom Cabin

Enjoy tranquility and peace on one-thousand acres of beautiful land. Catch glimpses of wildlife, enjoy refreshing walks, and sit around the fire while recharging. (No Hunting)