Holiday houses 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.

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

Secluded Riverfront Cabin Skylights, High Ceiling

Escape to this stunning riverfront cabin surrounded by towering oak trees and peaceful nature. With soaring ceilings, three large skylights, and expansive windows, the home is filled with natural light and beautiful river views. Enjoy an open kitchen and living area, a canopy queen master bed, plus two additional private sleeping spaces separated by curtains for comfort and flexibility. Relax in the spa-like bathroom featuring a soaking tub, tiled walk-in shower, and double sinks.

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.

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.

Lake Escape

Relax with the whole family at this peaceful place to stay. This home offers a place to get away and enjoy the views from your own private secluded lake. The house includes a king size bed with 2 additional bedrooms and 2 bathrooms. Enjoy the large patio with gas grill and plenty of outdoor space to explore. Bring your fishing pole and enjoy catching bass off of the new dock in the stocked lake. This house is the perfect place to get away and enjoy the outdoors.

"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.

The Hideaway Treehouse: Romantic Fireplace & View

Escape to The Hideaway in the Trees! 🌳 Spring brings birdsong through our massive picture window, just minutes from GCSU & downtown Milledgeville. Enjoy a cozy gas fireplace, queen bed, and rainfall shower. The kitchenette features a Keurig, cooktop, and toaster oven (no oven), plus a park-style BBQ and fire pit outside. With fast WiFi and cold A/C, it’s the perfect blend of childhood wonder and modern comfort. 🌿 Book your peaceful spring retreat today! ✨

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.

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.