Holiday rentals in Toomsboro

Adorable 1-bedroom guesthouse on the river

Kick back and relax in this calm, stylish woodland space. Just 7 miles off 1-16 on the Oconee River. Dublin is 15 min. away. Carl Vinson VA Hospital and Fairview Park Hospital 20 min. away. Southern Pines 12 min. Extra large bedroom with queen bed and loft. Can accommodate at least 4 adults, 2 small children. Full kitchen with bar. Amenities include internet, cable, VCR. Air& heat. All linens, dishes, and 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!

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.

Cozy Wooded Cabin w/ Tub, Rain Shower & Pergola

Summer Tiny House Hideaway! ☀️ Escape to this gorgeous Milledgeville gem, tucked in a cool, wooded retreat just 5 minutes from downtown. Beat the summer heat with a refreshing rinse in your private outdoor rain shower under the stars, or hide out in the crisp AC and soak in the luxury indoor tub with a Smart TV. End your warm summer nights cozying up by the fire pit or relaxing under the pergola. Perfect for couples or friends looking to sneak away, connect, and unwind!

Tiny Cabin in the Country

Our tiny cabin is on a secluded, wooded 20 acre homestead in a very rural area. It's a quiet place where everyone is welcome. There is almost no light pollution here; on a clear night you'll have an amazing view of the stars. The cabin has internet and a smart TV. We're one mile from downtown Irwinton's gas station, local diner, small local market, and Dollar General. Dublin, Macon, Milledgeville, I-75 and I-16 are all about a 30 minute easy drive with little traffic.

"Wimberly Plantation-Gleesom Hall" 3br Guest House

Charming guest house located on the grounds of historic "Gleesom Hall", an antebellum home built in 1844. There are 27 acres to enjoy, with azaleas, dogwoods, camellias, honeysuckle, and wildlife. Located within 25 minutes of Downtown Macon or Warner Robins AFB, and 35 minutes from Dublin. Gleesom Hall is inhabited by 7th and 8th generation descendants of the original family. Great place for enjoying country peace and quiet in a wonderful, historic setting.

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.

Inspirational Lake Front Escape

This is a weekend escape unlike any other. Enjoy breath taking views from almost every room! Dock is great for fishing or just taking in the inspirational views! This property also has a private boat ramp across the street- so bring your boat!! It can be tied off to the dock for easy weekend use! Newly renovated inside and out. New furniture, appliances, and dock! Water is only about 30 ft from door! Gradual slope to water

Pet Friendly|FencedYard|Dock|Beach|PrivateBoatRamp

License STR2026 159. Two bedroom Lake Sinclair waterfront home with king bedroom plus bunk room sleeping up to 4 guests. Massive private fenced point lot includes private boat ramp, two large docks, pavilion with fire pit, and panoramic lake views. Paddleboard, kayak, pool floats, bucket golf, and cornhole provided. Updated kitchen with coffee bar, lake view, and back deck with propane grill.

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.